{5,5′-Dimeth­oxy-2,2′-[1,1′-(2,2-dimethyl­propane-1,3-diyldinitrilo)­diethyl­idyne]diphenolato-κ4O,N,N′,O′}copper(II) monohydrate

Ghaemi, A.; Rayati, S.; Elahi, E.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681103889X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1445-m1446

https://doi.org/10.1107/S160053681103889X

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{5,5′-Dimethoxy-2,2′-[1,1′-(2,2-dimethylpropane-1,3-diyldinitrilo)diethylidyne]diphenolato-κ⁴O,N,N′,O′}copper(II) monohydrate

Akbar Ghaemi,^a ‡ Saeed Rayati,^b Ehsan Elahi,^a Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, Saveh Branch, Islamic Azad University, Saveh, Iran, ^bDepartment of Chemistry, K. N. Toosi University of Technology, PO Box, 16315-1618, Tehran, Iran, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 21 September 2011; accepted 22 September 2011; online 30 September 2011)

The tetradentate dianion in the title complex hydrate, [Cu(C₂₃H₂₈N₂O₄)]·H₂O, provides the Cu^II atom with a cis-N₂O₂ donor set. There is a significant twist from a regular square-planar geometry with the dihedral angle formed between the two six-membered CuOC₃N chelate rings being 32.14 (8)°. The water molecule forms hydrogen bonds to each of the coordinating O atoms of a given complex molecule. Supramolecular layers in the bc plane are formed in the crystal packing through C—H⋯O and C—H⋯π interactions.

Related literature

For the catalytic potential of Schiff base complexes of Cu^II, see: Gupta & Sutar (2008 ); Rayati et al. (2010 ). For the structure of the ligand, see: Ghaemi et al. (2011 ). For crystallization conditions, see: Harrowfield et al. (1996 ).

Experimental

Crystal data

[Cu(C₂₃H₂₈N₂O₄)]·H₂O
M_r = 478.03
Triclinic, $[P \overline 1]$
a = 10.4721 (7) Å
b = 10.8023 (9) Å
c = 10.8487 (7) Å
α = 106.699 (7)°
β = 99.823 (5)°
γ = 100.035 (6)°
V = 1125.37 (14) Å³
Z = 2
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 294 K
0.40 × 0.40 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.643, T_max = 1.000
11143 measured reflections
5034 independent reflections
4332 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 0.99
5034 reflections
285 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—O2	1.8825 (16)
Cu—O3	1.8776 (15)
Cu—N1	1.9597 (17)
Cu—N2	1.9524 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯O2	0.84	2.12	2.832 (3)	142
O1w—H2w⋯O3	0.84	2.32	3.035 (3)	143
C7—H7c⋯O1wⁱ	0.96	2.55	3.476 (5)	163
C16—H16c⋯O2ⁱⁱ	0.96	2.52	3.409 (3)	153
C14—H14b⋯Cg1ⁱⁱ	0.97	2.62	3.426 (2)	141
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: https://doi.org/10.1107/S160053681103889X/hg5100sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103889X/hg5100Isup2.hkl

checkCIF report

Comment top

Synthetic copper(II) Schiff base complexes have long been of great interest because of their potential as catalysts in the oxidation of various organic compounds (Gupta & Sutar, 2008). In continuation of research in this field (Rayati et al., 2010), the title complex, (I), was investigated.

The tetradentate dianion in the title monohydrate, (I), Fig. 1, provides a cis-N₂O₂ donor set, Table 1. Three six-membered chelate rings are formed as a result of coordination of the dianion. The CuNC₃N ring adopts a half-chair conformation. While the CuOC₃N chelate ring containing the O3 atom approaches planarity with a r.m.s. deviation of 0.031 Å, the other ring displays significant distortions. Thus, the r.m.s. deviation for the O2-containing CuOC₃N chelate ring is 0.163 Å with maximum deviations of 0.162 (2) Å for atom O2 and -0.159 (1) Å for the Cu atom. The dihedral angle formed between the two CuOC₃N chelate rings is 32.14 (8)° indicating a significant distortion from a regular square planar geometry. Each of the methoxy groups is co-planar with the benzene ring to which it is attached as seen in the values of the C7—O1—C3—C2 and C23—O4—C20—C19 of -0.8 (4) and -179.3 (3)°, respectively. The water molecule of solvation is associated with the complex, forming a bridge via its hydrogen atoms between the two coordinated oxygen atoms, Table 2.

The crystal packing features C—H···O and C—H···π interactions, Table 2, that assemble molecules into layers in the bc plane, Fig. 2, which stack along the a axis, Fig. 3.

Related literature top

For the catalytic potential of Schiff base complexes of Cu^II, see: Gupta & Sutar (2008); Rayati et al. (2010). For the structure of the ligand, see: Ghaemi et al. (2011). For crystallization conditions, see: Harrowfield et al. (1996).

Experimental top

The title complex was obtained by the template method in a branch tube (Harrowfield et al., 1996). The recently described (Ghaemi et al., 2011) N,N'-bis(2-hydroxy-4-methoxyacetophenone)-2,2-dimethylpropane-1,3-diamine (0.40 g, 1 mmol) and copper(II) acetate monohydrate (0.199 g, 1 mmol) were placed in the main arm of a branched tube. Ethanol was added to fill both arms. The tube was sealed and the main arm immersed in an oil bath at 333 K while the other was held at ambient temperature. After one week, crystals deposited in the cooler arm. These were filtered off and air dried. Yield: 75%. FT—IR data: ν(C═N) 1595 cm^-1.

Structure description top

The crystal packing features C—H···O and C—H···π interactions, Table 2, that assemble molecules into layers in the bc plane, Fig. 2, which stack along the a axis, Fig. 3.

For the catalytic potential of Schiff base complexes of Cu^II, see: Gupta & Sutar (2008); Rayati et al. (2010). For the structure of the ligand, see: Ghaemi et al. (2011). For crystallization conditions, see: Harrowfield et al. (1996).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular layer in the bc plane in (I) sustained by C—H···O and C—H···π interactions shown as blue and black dashed lines, respectively. The O—H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 3. A view in projection down the c axis of the unit-cell contents of (I), highlighting the stacking of layers along the a axis. The C—H···O and C—H···π interactions shown as blue and black dashed lines, respectively, and the O—H···O hydrogen bonds are shown as orange dashed lines.

{5,5'-Dimethoxy-2,2'-[1,1'-(2,2-dimethylpropane-1,3-diyldinitrilo)diethylidyne]diphenolato-κ⁴O,N,N',O'}copper(II) monohydrate top

Crystal data top

[Cu(C₂₃H₂₈N₂O₄)]·H₂O	Z = 2
M_r = 478.03	F(000) = 502
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4721 (7) Å	Cell parameters from 5694 reflections
b = 10.8023 (9) Å	θ = 2.3–29.3°
c = 10.8487 (7) Å	µ = 1.01 mm⁻¹
α = 106.699 (7)°	T = 294 K
β = 99.823 (5)°	Block, dark-brown
γ = 100.035 (6)°	0.40 × 0.40 × 0.20 mm
V = 1125.37 (14) Å³

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	5034 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4332 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.024
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scan	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→13
T_min = 0.643, T_max = 1.000	l = −14→11
11143 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0531P)² + 0.3861P] where P = (F_o² + 2F_c²)/3
5034 reflections	(Δ/σ)_max = 0.002
285 parameters	Δρ_max = 0.26 e Å⁻³
6 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Cu(C₂₃H₂₈N₂O₄)]·H₂O	γ = 100.035 (6)°
M_r = 478.03	V = 1125.37 (14) Å³
Triclinic, P1	Z = 2
a = 10.4721 (7) Å	Mo Kα radiation
b = 10.8023 (9) Å	µ = 1.01 mm⁻¹
c = 10.8487 (7) Å	T = 294 K
α = 106.699 (7)°	0.40 × 0.40 × 0.20 mm
β = 99.823 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	5034 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4332 reflections with I > 2σ(I)
T_min = 0.643, T_max = 1.000	R_int = 0.024
11143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 0.99	Δρ_max = 0.26 e Å⁻³
5034 reflections	Δρ_min = −0.47 e Å⁻³
285 parameters

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	U_iso*/U_eq
Cu	0.48963 (3)	0.47337 (3)	0.24182 (2)	0.04175 (11)
O1	0.04084 (19)	−0.0426 (2)	−0.1635 (2)	0.0746 (6)
O2	0.40205 (16)	0.30214 (16)	0.12419 (15)	0.0519 (4)
O3	0.62185 (18)	0.39699 (17)	0.30882 (16)	0.0580 (5)
O4	0.96607 (19)	0.3235 (2)	0.60237 (19)	0.0702 (5)
O1w	0.5646 (3)	0.1173 (3)	0.1144 (3)	0.1143 (10)
H1w	0.4956	0.1403	0.0867	0.171*
H2w	0.6121	0.1815	0.1794	0.171*
N1	0.40191 (19)	0.55577 (19)	0.12292 (18)	0.0440 (4)
N2	0.54285 (18)	0.63414 (17)	0.39652 (18)	0.0404 (4)
C1	0.2881 (2)	0.2697 (2)	0.0363 (2)	0.0429 (5)
C2	0.2249 (2)	0.1342 (2)	−0.0152 (2)	0.0472 (5)
H2	0.2638	0.0743	0.0155	0.057*
C3	0.1068 (2)	0.0873 (3)	−0.1098 (2)	0.0553 (6)
C4	0.0476 (3)	0.1766 (3)	−0.1551 (3)	0.0685 (8)
H4	−0.0329	0.1462	−0.2182	0.082*
C5	0.1076 (3)	0.3079 (3)	−0.1070 (3)	0.0607 (7)
H5	0.0664	0.3657	−0.1392	0.073*
C6	0.2299 (2)	0.3623 (2)	−0.0100 (2)	0.0461 (5)
C7	0.0998 (3)	−0.1364 (3)	−0.1189 (3)	0.0780 (9)
H7A	0.0449	−0.2245	−0.1647	0.117*
H7B	0.1071	−0.1161	−0.0255	0.117*
H7C	0.1869	−0.1317	−0.1367	0.117*
C8	0.2965 (2)	0.5025 (3)	0.0267 (2)	0.0481 (6)
C9	0.2384 (3)	0.5809 (3)	−0.0542 (3)	0.0696 (8)
H9A	0.2902	0.6711	−0.0212	0.104*
H9B	0.1480	0.5795	−0.0475	0.104*
H9C	0.2401	0.5420	−0.1452	0.104*
C10	0.4828 (3)	0.6911 (2)	0.1535 (2)	0.0520 (6)
H10A	0.4573	0.7230	0.0801	0.062*
H10B	0.5759	0.6882	0.1623	0.062*
C11	0.4675 (3)	0.7898 (2)	0.2811 (3)	0.0511 (6)
C12	0.3407 (3)	0.8406 (3)	0.2542 (3)	0.0714 (8)
H12A	0.3482	0.8891	0.1932	0.107*
H12B	0.3301	0.8980	0.3358	0.107*
H12C	0.2646	0.7665	0.2170	0.107*
C13	0.5910 (3)	0.9054 (3)	0.3299 (3)	0.0732 (8)
H13A	0.5994	0.9441	0.2615	0.110*
H13B	0.6688	0.8732	0.3519	0.110*
H13C	0.5822	0.9713	0.4070	0.110*
C14	0.4513 (2)	0.7208 (2)	0.3848 (2)	0.0456 (5)
H14A	0.4652	0.7883	0.4703	0.055*
H14B	0.3604	0.6681	0.3623	0.055*
C15	0.6363 (2)	0.6611 (2)	0.5039 (2)	0.0434 (5)
C16	0.6651 (3)	0.7919 (2)	0.6149 (3)	0.0632 (7)
H16A	0.6322	0.8562	0.5812	0.095*
H16B	0.7596	0.8230	0.6508	0.095*
H16C	0.6218	0.7794	0.6831	0.095*
C17	0.7159 (2)	0.5667 (2)	0.5215 (2)	0.0423 (5)
C18	0.8061 (3)	0.5949 (3)	0.6445 (2)	0.0564 (6)
H18	0.8115	0.6730	0.7120	0.068*
C19	0.8854 (3)	0.5134 (3)	0.6686 (3)	0.0635 (7)
H19	0.9418	0.5351	0.7516	0.076*
C20	0.8819 (2)	0.3976 (3)	0.5691 (2)	0.0508 (6)
C21	0.7941 (2)	0.3632 (2)	0.4486 (2)	0.0459 (5)
H21	0.7917	0.2854	0.3822	0.055*
C22	0.7074 (2)	0.4443 (2)	0.4242 (2)	0.0425 (5)
C23	0.9685 (3)	0.2051 (4)	0.5051 (3)	0.0800 (9)
H23A	1.0308	0.1625	0.5422	0.120*
H23B	0.9951	0.2259	0.4315	0.120*
H23C	0.8812	0.1465	0.4754	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.04730 (18)	0.04062 (18)	0.03637 (16)	0.01857 (13)	0.00166 (12)	0.01100 (12)
O1	0.0582 (11)	0.0691 (13)	0.0700 (12)	0.0033 (10)	−0.0159 (10)	0.0074 (10)
O2	0.0550 (9)	0.0437 (9)	0.0456 (9)	0.0209 (8)	−0.0136 (7)	0.0063 (7)
O3	0.0669 (11)	0.0539 (10)	0.0417 (8)	0.0319 (9)	−0.0107 (8)	0.0014 (7)
O4	0.0647 (12)	0.0861 (14)	0.0622 (11)	0.0343 (11)	−0.0056 (9)	0.0297 (11)
O1w	0.0964 (18)	0.0788 (16)	0.153 (2)	0.0434 (14)	−0.0017 (17)	0.0207 (17)
N1	0.0504 (10)	0.0491 (11)	0.0414 (9)	0.0236 (9)	0.0130 (8)	0.0198 (8)
N2	0.0443 (10)	0.0368 (9)	0.0434 (9)	0.0130 (8)	0.0108 (8)	0.0154 (8)
C1	0.0449 (12)	0.0550 (13)	0.0294 (9)	0.0224 (10)	0.0044 (9)	0.0110 (9)
C2	0.0471 (12)	0.0536 (14)	0.0371 (11)	0.0195 (11)	0.0007 (9)	0.0099 (10)
C3	0.0486 (13)	0.0643 (16)	0.0437 (12)	0.0144 (12)	0.0010 (10)	0.0087 (12)
C4	0.0521 (15)	0.087 (2)	0.0535 (15)	0.0173 (15)	−0.0137 (12)	0.0185 (15)
C5	0.0559 (15)	0.0807 (19)	0.0504 (14)	0.0302 (14)	−0.0010 (12)	0.0283 (14)
C6	0.0480 (12)	0.0607 (15)	0.0348 (10)	0.0256 (11)	0.0063 (9)	0.0178 (10)
C7	0.0662 (18)	0.0586 (17)	0.086 (2)	0.0091 (15)	−0.0071 (16)	0.0059 (16)
C8	0.0545 (13)	0.0627 (15)	0.0400 (11)	0.0308 (12)	0.0133 (10)	0.0251 (11)
C9	0.0762 (19)	0.079 (2)	0.0666 (17)	0.0324 (16)	0.0040 (14)	0.0419 (16)
C10	0.0565 (14)	0.0581 (15)	0.0553 (14)	0.0217 (12)	0.0194 (11)	0.0313 (12)
C11	0.0610 (14)	0.0421 (12)	0.0596 (14)	0.0211 (11)	0.0165 (12)	0.0242 (11)
C12	0.087 (2)	0.0629 (17)	0.0770 (19)	0.0444 (16)	0.0179 (16)	0.0274 (15)
C13	0.084 (2)	0.0560 (16)	0.081 (2)	0.0073 (15)	0.0165 (17)	0.0320 (15)
C14	0.0522 (13)	0.0409 (12)	0.0482 (12)	0.0187 (10)	0.0169 (10)	0.0136 (10)
C15	0.0487 (12)	0.0373 (11)	0.0406 (11)	0.0041 (10)	0.0098 (10)	0.0113 (9)
C16	0.086 (2)	0.0412 (13)	0.0514 (14)	0.0139 (13)	0.0024 (13)	0.0066 (11)
C17	0.0414 (11)	0.0394 (11)	0.0411 (11)	0.0037 (9)	0.0021 (9)	0.0136 (9)
C18	0.0568 (14)	0.0482 (14)	0.0470 (13)	0.0036 (12)	−0.0092 (11)	0.0069 (11)
C19	0.0554 (15)	0.0667 (17)	0.0531 (14)	0.0070 (13)	−0.0161 (12)	0.0173 (13)
C20	0.0406 (12)	0.0599 (15)	0.0524 (13)	0.0119 (11)	0.0003 (10)	0.0252 (12)
C21	0.0434 (12)	0.0536 (14)	0.0422 (11)	0.0174 (10)	0.0060 (9)	0.0169 (10)
C22	0.0400 (11)	0.0478 (12)	0.0378 (11)	0.0098 (10)	0.0018 (9)	0.0157 (9)
C23	0.082 (2)	0.099 (2)	0.077 (2)	0.056 (2)	0.0146 (17)	0.0381 (19)

Geometric parameters (Å, º) top

Cu—O2	1.8825 (16)	C9—H9C	0.9600
Cu—O3	1.8776 (15)	C10—C11	1.538 (3)
Cu—N1	1.9597 (17)	C10—H10A	0.9700
Cu—N2	1.9524 (18)	C10—H10B	0.9700
O1—C3	1.358 (3)	C11—C13	1.528 (4)
O1—C7	1.428 (3)	C11—C14	1.535 (3)
O2—C1	1.316 (3)	C11—C12	1.538 (3)
O3—C22	1.312 (3)	C12—H12A	0.9600
O4—C20	1.361 (3)	C12—H12B	0.9600
O4—C23	1.412 (4)	C12—H12C	0.9600
O1w—H1w	0.8400	C13—H13A	0.9600
O1w—H2w	0.8400	C13—H13B	0.9600
N1—C8	1.296 (3)	C13—H13C	0.9600
N1—C10	1.469 (3)	C14—H14A	0.9700
N2—C15	1.310 (3)	C14—H14B	0.9700
N2—C14	1.466 (3)	C15—C17	1.458 (3)
C1—C2	1.400 (3)	C15—C16	1.512 (3)
C1—C6	1.421 (3)	C16—H16A	0.9600
C2—C3	1.374 (3)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.390 (4)	C17—C22	1.412 (3)
C4—C5	1.353 (4)	C17—C18	1.414 (3)
C4—H4	0.9300	C18—C19	1.359 (4)
C5—C6	1.420 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.387 (4)
C6—C8	1.459 (4)	C19—H19	0.9300
C7—H7A	0.9600	C20—C21	1.373 (3)
C7—H7B	0.9600	C21—C22	1.411 (3)
C7—H7C	0.9600	C21—H21	0.9300
C8—C9	1.511 (3)	C23—H23A	0.9600
C9—H9A	0.9600	C23—H23B	0.9600
C9—H9B	0.9600	C23—H23C	0.9600

O3—Cu—O2	87.70 (7)	C13—C11—C10	107.4 (2)
O3—Cu—N2	93.30 (7)	C14—C11—C10	110.41 (18)
O2—Cu—N2	161.99 (8)	C13—C11—C12	110.3 (2)
O3—Cu—N1	156.09 (8)	C14—C11—C12	106.3 (2)
O2—Cu—N1	91.13 (7)	C10—C11—C12	110.7 (2)
N2—Cu—N1	95.08 (8)	C11—C12—H12A	109.5
C3—O1—C7	117.2 (2)	C11—C12—H12B	109.5
C1—O2—Cu	126.53 (14)	H12A—C12—H12B	109.5
C22—O3—Cu	128.03 (15)	C11—C12—H12C	109.5
C20—O4—C23	118.3 (2)	H12A—C12—H12C	109.5
H1w—O1w—H2w	107.4	H12B—C12—H12C	109.5
C8—N1—C10	123.47 (19)	C11—C13—H13A	109.5
C8—N1—Cu	128.32 (17)	C11—C13—H13B	109.5
C10—N1—Cu	108.06 (14)	H13A—C13—H13B	109.5
C15—N2—C14	121.92 (19)	C11—C13—H13C	109.5
C15—N2—Cu	127.82 (15)	H13A—C13—H13C	109.5
C14—N2—Cu	109.93 (14)	H13B—C13—H13C	109.5
O2—C1—C2	116.13 (19)	N2—C14—C11	114.24 (18)
O2—C1—C6	124.1 (2)	N2—C14—H14A	108.7
C2—C1—C6	119.7 (2)	C11—C14—H14A	108.7
C3—C2—C1	121.7 (2)	N2—C14—H14B	108.7
C3—C2—H2	119.1	C11—C14—H14B	108.7
C1—C2—H2	119.1	H14A—C14—H14B	107.6
O1—C3—C2	124.5 (2)	N2—C15—C17	121.6 (2)
O1—C3—C4	116.1 (2)	N2—C15—C16	120.9 (2)
C2—C3—C4	119.4 (3)	C17—C15—C16	117.5 (2)
C5—C4—C3	119.7 (2)	C15—C16—H16A	109.5
C5—C4—H4	120.1	C15—C16—H16B	109.5
C3—C4—H4	120.1	H16A—C16—H16B	109.5
C4—C5—C6	123.6 (2)	C15—C16—H16C	109.5
C4—C5—H5	118.2	H16A—C16—H16C	109.5
C6—C5—H5	118.2	H16B—C16—H16C	109.5
C5—C6—C1	115.8 (2)	C22—C17—C18	116.3 (2)
C5—C6—C8	120.7 (2)	C22—C17—C15	124.43 (19)
C1—C6—C8	123.2 (2)	C18—C17—C15	119.3 (2)
O1—C7—H7A	109.5	C19—C18—C17	123.1 (2)
O1—C7—H7B	109.5	C19—C18—H18	118.5
H7A—C7—H7B	109.5	C17—C18—H18	118.5
O1—C7—H7C	109.5	C18—C19—C20	119.9 (2)
H7A—C7—H7C	109.5	C18—C19—H19	120.1
H7B—C7—H7C	109.5	C20—C19—H19	120.1
N1—C8—C6	121.1 (2)	O4—C20—C21	124.7 (2)
N1—C8—C9	122.0 (2)	O4—C20—C19	115.5 (2)
C6—C8—C9	116.9 (2)	C21—C20—C19	119.7 (2)
C8—C9—H9A	109.4	C20—C21—C22	120.9 (2)
C8—C9—H9B	109.4	C20—C21—H21	119.6
H9A—C9—H9B	109.5	C22—C21—H21	119.6
C8—C9—H9C	109.6	O3—C22—C21	115.4 (2)
H9A—C9—H9C	109.5	O3—C22—C17	124.6 (2)
H9B—C9—H9C	109.5	C21—C22—C17	119.95 (19)
N1—C10—C11	113.23 (19)	O4—C23—H23A	109.5
N1—C10—H10A	108.9	O4—C23—H23B	109.5
C11—C10—H10A	108.9	H23A—C23—H23B	109.5
N1—C10—H10B	108.9	O4—C23—H23C	109.5
C11—C10—H10B	108.9	H23A—C23—H23C	109.5
H10A—C10—H10B	107.7	H23B—C23—H23C	109.5
C13—C11—C14	111.8 (2)

O3—Cu—O2—C1	178.8 (2)	C5—C6—C8—N1	174.0 (2)
N2—Cu—O2—C1	85.3 (3)	C1—C6—C8—N1	−13.1 (3)
N1—Cu—O2—C1	−25.1 (2)	C5—C6—C8—C9	−7.1 (3)
O2—Cu—O3—C22	−158.8 (2)	C1—C6—C8—C9	165.8 (2)
N2—Cu—O3—C22	3.2 (2)	C8—N1—C10—C11	108.3 (3)
N1—Cu—O3—C22	113.6 (2)	Cu—N1—C10—C11	−76.0 (2)
O3—Cu—N1—C8	104.7 (3)	N1—C10—C11—C13	158.1 (2)
O2—Cu—N1—C8	17.8 (2)	N1—C10—C11—C14	36.0 (3)
N2—Cu—N1—C8	−145.2 (2)	N1—C10—C11—C12	−81.4 (2)
O3—Cu—N1—C10	−70.8 (2)	C15—N2—C14—C11	113.8 (2)
O2—Cu—N1—C10	−157.67 (15)	Cu—N2—C14—C11	−72.3 (2)
N2—Cu—N1—C10	39.26 (15)	C13—C11—C14—N2	−75.8 (3)
O3—Cu—N2—C15	−2.6 (2)	C10—C11—C14—N2	43.7 (3)
O2—Cu—N2—C15	90.1 (3)	C12—C11—C14—N2	163.8 (2)
N1—Cu—N2—C15	−160.20 (19)	C14—N2—C15—C17	172.1 (2)
O3—Cu—N2—C14	−176.04 (14)	Cu—N2—C15—C17	−0.6 (3)
O2—Cu—N2—C14	−83.4 (2)	C14—N2—C15—C16	−7.6 (3)
N1—Cu—N2—C14	26.38 (15)	Cu—N2—C15—C16	179.70 (18)
Cu—O2—C1—C2	−163.66 (16)	N2—C15—C17—C22	4.5 (4)
Cu—O2—C1—C6	18.1 (3)	C16—C15—C17—C22	−175.7 (2)
O2—C1—C2—C3	−178.5 (2)	N2—C15—C17—C18	−173.7 (2)
C6—C1—C2—C3	−0.2 (3)	C16—C15—C17—C18	6.0 (3)
C7—O1—C3—C2	−0.8 (4)	C22—C17—C18—C19	2.6 (4)
C7—O1—C3—C4	179.8 (3)	C15—C17—C18—C19	−179.0 (2)
C1—C2—C3—O1	−180.0 (2)	C17—C18—C19—C20	1.4 (4)
C1—C2—C3—C4	−0.6 (4)	C23—O4—C20—C21	2.8 (4)
O1—C3—C4—C5	−179.7 (3)	C23—O4—C20—C19	−179.3 (3)
C2—C3—C4—C5	0.9 (4)	C18—C19—C20—O4	179.2 (2)
C3—C4—C5—C6	−0.4 (5)	C18—C19—C20—C21	−2.9 (4)
C4—C5—C6—C1	−0.3 (4)	O4—C20—C21—C22	178.0 (2)
C4—C5—C6—C8	173.1 (3)	C19—C20—C21—C22	0.3 (4)
O2—C1—C6—C5	178.8 (2)	Cu—O3—C22—C21	178.78 (16)
C2—C1—C6—C5	0.7 (3)	Cu—O3—C22—C17	−0.6 (4)
O2—C1—C6—C8	5.6 (3)	C20—C21—C22—O3	−175.6 (2)
C2—C1—C6—C8	−172.6 (2)	C20—C21—C22—C17	3.9 (4)
C10—N1—C8—C6	172.0 (2)	C18—C17—C22—O3	174.3 (2)
Cu—N1—C8—C6	−2.9 (3)	C15—C17—C22—O3	−4.0 (4)
C10—N1—C8—C9	−6.9 (4)	C18—C17—C22—C21	−5.1 (3)
Cu—N1—C8—C9	178.26 (18)	C15—C17—C22—C21	176.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O2	0.84	2.12	2.832 (3)	142
O1w—H2w···O3	0.84	2.32	3.035 (3)	143
C7—H7c···O1wⁱ	0.96	2.55	3.476 (5)	163
C16—H16c···O2ⁱⁱ	0.96	2.52	3.409 (3)	153
C14—H14b···Cg1ⁱⁱ	0.97	2.62	3.426 (2)	141

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

Experimental details

Crystal data
Chemical formula	[Cu(C₂₃H₂₈N₂O₄)]·H₂O
M_r	478.03
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	10.4721 (7), 10.8023 (9), 10.8487 (7)
α, β, γ (°)	106.699 (7), 99.823 (5), 100.035 (6)
V (Å³)	1125.37 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.643, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11143, 5034, 4332
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 0.99
No. of reflections	5034
No. of parameters	285
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.47

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu—O2	1.8825 (16)	Cu—N1	1.9597 (17)
Cu—O3	1.8776 (15)	Cu—N2	1.9524 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O2	0.84	2.12	2.832 (3)	142
O1w—H2w···O3	0.84	2.32	3.035 (3)	143
C7—H7c···O1wⁱ	0.96	2.55	3.476 (5)	163
C16—H16c···O2ⁱⁱ	0.96	2.52	3.409 (3)	153
C14—H14b···Cg1ⁱⁱ	0.97	2.62	3.426 (2)	141

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

Footnotes

‡Additional correspondence author, e-mail: akbarghaemi@yahoo.com.

Acknowledgements

We gratefully acknowledge practical support of this study by K. N. Toosi University of Technology, Islamic Azad University (Saveh Branch), and thank the University of Malaya for supporting the crystallographic facility.

References

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