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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages m205-m206
https://doi.org/10.1107/S205698901501960X

Crystal structure of {2-[({2-[(2-amino­ethyl)amino]­ethyl}imino)­meth­yl]-6-hy­dr­oxy­phenolato-κ4N,N′,N′′,O1}(nitrato-κO)copper(II) ethanol 0.25-solvate

Shabana Noor,a* Sarvendra Kumar,b* Suhail Sabir,a Rüdiger W. Seidelc and Richard Goddardc

aDepartment of Chemistry, Aligarh Muslim University, Aligarh, 202 002, India, bFaculty of Pharmaceutical Science, Tokyo University of Science, Noda, Japan, and cMax-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz-1, 45470 Mülheim an der Ruhr, Germany
*Correspondence e-mail: shabanachem0711@gmail.com, s.kumar@msn.com

Edited by T. N. Guru Row, Indian Institute of Science, India (Received 15 September 2015; accepted 16 October 2015; online 24 October 2015)

In the crystal structure of the title mononuclear CuII complex, [Cu(C11H16N3O2)(NO3)]·0.25C2H5OH, the complex molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a dimer with an approximate non-crystallographic twofold rotation axis of symmetry. In the monomeric unit, the Cu2+ ion exhibits a distorted square-pyramidal configuration, whereby the anionic [HL]− Schiff base ligand binds in a tetradentate fashion via the O and the three N atoms which all are approximately coplanar. The O atom of a nitrate anion occupies the fifth coordination site, causing the CuII atom to move slightly out of the approximate basal plane toward the bound nitrate group. The structure exhibits disorder of the ethanol solvent mol­ecule.

CCDC reference: 1410216

Similar articles

1. Related literature

For the corresponding Schiff base, see: Osterbere (1974[Osterbere, R. (1974). Coord. Chem. Rev. 12, 309-347.]); Patterson & Holm (1975[Patterson, G. S. & Holm, R. H. (1975). Bioinorg. Chem. 4, 257-275.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Cu(C11H16N3O2)(NO3)]·0.25C2H6O

  • Mr = 359.33

  • Monoclinic, P 21 /n

  • a = 11.952 (2) Å

  • b = 12.129 (2) Å

  • c = 19.590 (4) Å

  • β = 98.921 (3)°

  • V = 2805.5 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.59 mm−1

  • T = 100 K

  • 0.16 × 0.11 × 0.08 mm

2.2. Data collection

  • Bruker AXS KappaCCD diffractometer

  • Absorption correction: Gaussian (SADABS; Bruker, 2013[Bruker (2013). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.805, Tmax = 0.879

  • 106043 measured reflections

  • 14120 independent reflections

  • 10834 reflections with I > 2σ(I)

  • Rint = 0.059

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.112

  • S = 1.07

  • 14120 reflections

  • 406 parameters

  • 29 restraints

  • H-atom parameters constrained

  • Δρmax = 1.06 e Å−3

  • Δρmin = −1.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯O1 0.84 2.28 2.7243 (18) 114
O2—H2⋯O6 0.84 1.93 2.6969 (18) 151
N2—H2A⋯O5 1.00 2.13 2.968 (2) 140
N2—H2A⋯O10i 1.00 2.29 3.017 (2) 129
N3—H3A⋯O8 0.91 2.25 3.126 (2) 162
N3—H3B⋯O2ii 0.91 2.36 3.138 (2) 143
N3—H3B⋯O7 0.91 2.47 3.071 (2) 124
O7—H7A⋯O1 0.84 1.98 2.7365 (18) 150
O7—H7A⋯O6 0.84 2.26 2.7096 (18) 114
N6—H6⋯O5iii 1.00 2.10 2.960 (2) 143
N6—H6⋯O10 1.00 2.34 3.067 (2) 129
N7—H7B⋯O3 0.91 2.04 2.932 (2) 167
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2013[Bruker (2013). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg, & Berndt, 1999[Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).

Supporting information

CCDC reference: 1410216

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S205698901501960X/gw2154sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901501960X/gw2154Isup2.hkl

checkCIF report


Structural commentary top

Schiff base ligands and their metal complexes have been the subject of research covering a vast area of metallo–organic as well as bio–inorganic chemistry (Osterbere, 1974; Patterson & Holm, 1975). The characteristic features of the coordination behaviour of metal ions with Schiff base ligands make the complexes useful in variety of catalytic transformations. Tetra­nuclear manganese clusters with alkoxo bridges have been proved as potential models to elaborate the mechanism of oxygen evolution by polypeptides in the oxidation of water in photosynthetic organisms.

The title compound crystallizes in the monoclinic space group P21/n with two crystallographic independent molecules of the complex, which differ essentially in the orientation of the nitrate group (Fig. 1). The complexes are linked by N—H···O and O—H···O hydrogen bonds to form a dimer with an approximate non-crystallographic 2-fold axis of symmetry, passing along a rough line described by the midpoints of Cu1 and Cu2, O3 and O8, N3 and N7, O1 and O6, and O2 and O7 (Fig. 2). In each monomer unit, the Cu2+ ion exhibits a distorted square-pyramidal configuration, whereby the anionic [HL] binds in tetra­dentate fashion via O and the three N atoms of the Schiff base ligand, which are approximately coplanar. The O atom of a nitrate anion occupies the fifth coordination site, causing the Cu atom to move slightly out of the approximate basal plane toward the bound nitrate group. For Cu1, this displacement is 0.167 Å above mean plane defined by O1, N1, N2 and N3, and for Cu2 it is 0.192 Å above the mean plane defined by O6, N5, N6 and N7. The Cu—N bond lengths (1.95-2.02 Å) are comparable with those of other structurally similar copper(II) complexes (1.95-2.28 Å). The Cu—O bond length to the apical O atom of the nitrate group at 2.36 (4) Å (mean) is significantly longer that the Cu—O bond length to the Schiff base ligand in the basal position of square pyramid [1.929 (1) Å (mean)]. The basal coordination planes of each CuII unit lie approximately perpendicular to one other (ca. 86ο) in the dimer, but this is not mirrored by the nitrate groups. The trigonality index τ values for the coordination spheres of the two independent Cu atoms are 0.16 and 0.03 [τ = (β-α)/60] where α and β are given by the main opposing angles in the coordination polyhedron (Fig.3). For perfect square pyramidal and trigonal bipyramidal coordination geometries, the values of τ are zero and unity, respectively. For Cu1 β = O(1)–Cu(1)–N(2) = 173.40 (6)° and α = N(1)–Cu(1)–N(3) = 163.61 (6)°] (Table 2). According to these values, the coordination geometry around both copper ions is best described as distorted square-pyramidal with one nitrate occupying the axial position. The relationship of coordination geometries of the Cu atoms of the monomer units in the dimer is shown in Fig. 3. Several of the NH groups of the ligands in the dimers are additionally involved in N—H···O hydrogen bonds to neighboring dimers [N3···O2 = 3.138 (2) Å, N6···O5 = 2.960 (2) Å, N2···O10 = 3.017 (2) Å].

Synthesis and crystallization top

To a stirred solution of H2L (0.4 mmol, 0.089 g) dissolved in 40 mL of EtOH/CH3CN (1:1), Cu(NO3)2·3H2O (0.4 mmol, 0.096 g) was added, followed by addition of Et3N (0.12 mmol, 0.16 mL). The resulting mixture was refluxed for 5–6 h. The reaction mixture was filtered. After 2-5 d, dark-green crystals were obtained by slow diffusion of di­ethyl ether into the solution. IR data (KBr cm-1): 1613 ν(-CH=N), 3231, 3252, 1443 ν(N–H), 1223 ν(Ar–OH), 1110 ν(C–O) ,585 ν(M–O), 540 ν(M–N).

Refinement top

The ethanol solvent molecule is disordered about a centre of symmetry and was thus refined with site occupancy factors of 0.5. The O11—C23 and C23—C24 distances were restrained to target values of 1.43 (4) and 1.54 (4) Å, respectively. Rigid bond restraints and restraints towards isotropy were applied to the anisotropic atomic displacement parameters. H atoms were added at geometrically calculated positions and refined with the appropriate riding model.

Related literature top

For the corresponding Schiff base, see: Osterbere (1974); Patterson & Holm (1975).

Structure description top

Schiff base ligands and their metal complexes have been the subject of research covering a vast area of metallo–organic as well as bio–inorganic chemistry (Osterbere, 1974; Patterson & Holm, 1975). The characteristic features of the coordination behaviour of metal ions with Schiff base ligands make the complexes useful in variety of catalytic transformations. Tetra­nuclear manganese clusters with alkoxo bridges have been proved as potential models to elaborate the mechanism of oxygen evolution by polypeptides in the oxidation of water in photosynthetic organisms.

The title compound crystallizes in the monoclinic space group P21/n with two crystallographic independent molecules of the complex, which differ essentially in the orientation of the nitrate group (Fig. 1). The complexes are linked by N—H···O and O—H···O hydrogen bonds to form a dimer with an approximate non-crystallographic 2-fold axis of symmetry, passing along a rough line described by the midpoints of Cu1 and Cu2, O3 and O8, N3 and N7, O1 and O6, and O2 and O7 (Fig. 2). In each monomer unit, the Cu2+ ion exhibits a distorted square-pyramidal configuration, whereby the anionic [HL] binds in tetra­dentate fashion via O and the three N atoms of the Schiff base ligand, which are approximately coplanar. The O atom of a nitrate anion occupies the fifth coordination site, causing the Cu atom to move slightly out of the approximate basal plane toward the bound nitrate group. For Cu1, this displacement is 0.167 Å above mean plane defined by O1, N1, N2 and N3, and for Cu2 it is 0.192 Å above the mean plane defined by O6, N5, N6 and N7. The Cu—N bond lengths (1.95-2.02 Å) are comparable with those of other structurally similar copper(II) complexes (1.95-2.28 Å). The Cu—O bond length to the apical O atom of the nitrate group at 2.36 (4) Å (mean) is significantly longer that the Cu—O bond length to the Schiff base ligand in the basal position of square pyramid [1.929 (1) Å (mean)]. The basal coordination planes of each CuII unit lie approximately perpendicular to one other (ca. 86ο) in the dimer, but this is not mirrored by the nitrate groups. The trigonality index τ values for the coordination spheres of the two independent Cu atoms are 0.16 and 0.03 [τ = (β-α)/60] where α and β are given by the main opposing angles in the coordination polyhedron (Fig.3). For perfect square pyramidal and trigonal bipyramidal coordination geometries, the values of τ are zero and unity, respectively. For Cu1 β = O(1)–Cu(1)–N(2) = 173.40 (6)° and α = N(1)–Cu(1)–N(3) = 163.61 (6)°] (Table 2). According to these values, the coordination geometry around both copper ions is best described as distorted square-pyramidal with one nitrate occupying the axial position. The relationship of coordination geometries of the Cu atoms of the monomer units in the dimer is shown in Fig. 3. Several of the NH groups of the ligands in the dimers are additionally involved in N—H···O hydrogen bonds to neighboring dimers [N3···O2 = 3.138 (2) Å, N6···O5 = 2.960 (2) Å, N2···O10 = 3.017 (2) Å].

For the corresponding Schiff base, see: Osterbere (1974); Patterson & Holm (1975).

Synthesis and crystallization top

To a stirred solution of H2L (0.4 mmol, 0.089 g) dissolved in 40 mL of EtOH/CH3CN (1:1), Cu(NO3)2·3H2O (0.4 mmol, 0.096 g) was added, followed by addition of Et3N (0.12 mmol, 0.16 mL). The resulting mixture was refluxed for 5–6 h. The reaction mixture was filtered. After 2-5 d, dark-green crystals were obtained by slow diffusion of di­ethyl ether into the solution. IR data (KBr cm-1): 1613 ν(-CH=N), 3231, 3252, 1443 ν(N–H), 1223 ν(Ar–OH), 1110 ν(C–O) ,585 ν(M–O), 540 ν(M–N).

Refinement details top

The ethanol solvent molecule is disordered about a centre of symmetry and was thus refined with site occupancy factors of 0.5. The O11—C23 and C23—C24 distances were restrained to target values of 1.43 (4) and 1.54 (4) Å, respectively. Rigid bond restraints and restraints towards isotropy were applied to the anisotropic atomic displacement parameters. H atoms were added at geometrically calculated positions and refined with the appropriate riding model.

Computing details top

Data collection: SMART (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, & Berndt, 1999) and Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top
[Figure 1] Fig. 1. Crystal structure of title complex, [Cu(HL)(NO3)]·0.25EtOH, showing the two independent molecules in the crystal in similar orientations with labelling of significant atoms (Solvent is omitted for clarity).
[Figure 2] Fig. 2. Dimer of the title complex, [Cu(HL)(NO3)]·0.25EtOH, showing the N—H···O and O—H···O hydrogen-bonding interactions. The approximate non-crystallographic 2-fold axis of symmetry of the dimer in the crystal is vertical. Selected distances (Å): N3···O8 2.931 (2), N7···O3 3.126 (2), O1···O7 2.697 (2), O2···O6 2.737 (2). Carbon-bound hydrogen atoms have been omitted for clarity.
[Figure 3] Fig. 3. Arrangement of atoms in dimers of title complex, [Cu(HL)(NO3)]·0.25EtOH, in the crystal, showing the relationship between the approximate coordination planes of the Cu atoms defined by the coordinating N and O atoms (angle between the mean planes in °).
{2-[({2-[(2-Aminoethyl)amino]ethyl}imino)methyl]-6-hydroxyphenolato-κ4N,N',N'',O1}(nitrato-κO)]copper(II) ethanol 0.25-solvate top
Crystal data top
[Cu(C11H16N3O2)(NO3)]·0.25C2H6OF(000) = 1484
Mr = 359.33Dx = 1.701 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.952 (2) ÅCell parameters from 10834 reflections
b = 12.129 (2) Åθ = 0.8–0.9°
c = 19.590 (4) ŵ = 1.59 mm−1
β = 98.921 (3)°T = 100 K
V = 2805.5 (9) Å3Prism, green
Z = 80.16 × 0.11 × 0.08 mm
Data collection top
Bruker AXS KappaCCD
diffractometer		10834 reflections with I > 2σ(I)
Radiation source: FR591 rotating anodeRint = 0.059
phi and ω scansθmax = 37.4°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		h = −20→20
Tmin = 0.805, Tmax = 0.879k = −20→20
106043 measured reflectionsl = −33→33
14120 independent reflections
Refinement top
Refinement on F229 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0392P)2 + 3.8944P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
14120 reflectionsΔρmax = 1.06 e Å−3
406 parametersΔρmin = −1.15 e Å−3
Crystal data top
[Cu(C11H16N3O2)(NO3)]·0.25C2H6OV = 2805.5 (9) Å3
Mr = 359.33Z = 8
Monoclinic, P21/nMo Kα radiation
a = 11.952 (2) ŵ = 1.59 mm−1
b = 12.129 (2) ÅT = 100 K
c = 19.590 (4) Å0.16 × 0.11 × 0.08 mm
β = 98.921 (3)°
Data collection top
Bruker AXS KappaCCD
diffractometer		14120 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		10834 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 0.879Rint = 0.059
106043 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04429 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.07Δρmax = 1.06 e Å−3
14120 reflectionsΔρmin = −1.15 e Å−3
406 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.56242 (2)0.22501 (2)0.31990 (2)0.01125 (4)
O10.67530 (10)0.33955 (10)0.32549 (6)0.0133 (2)
O20.79704 (11)0.52715 (11)0.31545 (7)0.0178 (2)
H20.75850.48930.28440.027*
O30.41682 (13)0.35390 (12)0.31382 (9)0.0280 (3)
O40.27794 (16)0.43188 (14)0.35387 (11)0.0373 (4)
O50.30557 (12)0.25521 (12)0.36722 (8)0.0217 (3)
N10.59587 (12)0.19043 (13)0.41797 (7)0.0149 (2)
N20.46006 (12)0.09379 (12)0.31626 (8)0.0140 (2)
H2A0.38330.12020.32310.017*
N30.53736 (12)0.21467 (12)0.21599 (8)0.0135 (2)
H3A0.52070.28230.19710.016*
H3B0.60100.18920.20110.016*
N40.33393 (13)0.34802 (13)0.34611 (8)0.0166 (3)
C10.72842 (13)0.38286 (14)0.38339 (8)0.0124 (2)
C20.79243 (14)0.48064 (14)0.37829 (9)0.0139 (3)
C30.85100 (15)0.53096 (15)0.43647 (9)0.0183 (3)
H30.89310.59620.43160.022*
C40.84897 (17)0.48710 (18)0.50225 (10)0.0222 (4)
H40.88960.52210.54190.027*
C50.78789 (17)0.39301 (18)0.50912 (9)0.0207 (3)
H50.78680.36300.55380.025*
C60.72649 (14)0.34007 (15)0.45065 (9)0.0152 (3)
C70.66276 (15)0.24331 (16)0.46398 (9)0.0174 (3)
H70.67110.21710.51020.021*
C80.53173 (16)0.09540 (16)0.43800 (10)0.0188 (3)
H8A0.46110.12070.45370.023*
H8B0.57750.05460.47630.023*
C90.50393 (15)0.02128 (14)0.37510 (10)0.0179 (3)
H9A0.5727−0.01800.36590.021*
H9B0.4462−0.03400.38270.021*
C100.44999 (16)0.04397 (15)0.24709 (10)0.0186 (3)
H10A0.3816−0.00300.23820.022*
H10B0.5171−0.00230.24350.022*
C110.44169 (15)0.13761 (15)0.19500 (9)0.0179 (3)
H11A0.44530.10800.14830.022*
H11B0.36870.17680.19370.022*
Cu20.53711 (2)0.58282 (2)0.19038 (2)0.01359 (5)
O60.66003 (10)0.47838 (11)0.19655 (6)0.0144 (2)
O70.78265 (11)0.28994 (11)0.21571 (7)0.0164 (2)
H7A0.75430.32880.24420.025*
O80.42326 (11)0.42812 (12)0.14803 (8)0.0209 (3)
O90.25873 (13)0.34741 (13)0.13124 (9)0.0269 (3)
O100.27202 (12)0.51948 (13)0.16051 (9)0.0273 (3)
N50.56098 (12)0.63534 (12)0.09942 (8)0.0154 (2)
N60.43573 (13)0.71478 (13)0.18807 (8)0.0164 (3)
H60.35790.69290.16590.020*
N70.51519 (14)0.56904 (13)0.28940 (8)0.0182 (3)
H7B0.49580.49860.29840.022*
H7C0.58080.58580.31770.022*
N80.31697 (13)0.43119 (12)0.14697 (8)0.0152 (2)
C120.69497 (13)0.43548 (13)0.14185 (8)0.0125 (3)
C130.75845 (13)0.33588 (14)0.15149 (9)0.0136 (3)
C140.79762 (15)0.28423 (14)0.09677 (9)0.0165 (3)
H140.83880.21720.10440.020*
C150.77738 (16)0.32950 (16)0.03034 (9)0.0193 (3)
H150.80430.2934−0.00700.023*
C160.71802 (16)0.42696 (16)0.01954 (9)0.0191 (3)
H160.70560.4586−0.02540.023*
C170.67533 (15)0.48069 (14)0.07403 (9)0.0154 (3)
C180.61363 (15)0.58271 (15)0.05751 (9)0.0164 (3)
H180.61220.61250.01250.020*
C190.50038 (15)0.73849 (15)0.07816 (10)0.0179 (3)
H19A0.42750.72230.04840.021*
H19B0.54640.78540.05190.021*
C200.47980 (16)0.79697 (15)0.14363 (10)0.0197 (3)
H20A0.55140.82900.16770.024*
H20B0.42430.85730.13220.024*
C210.43072 (17)0.74907 (15)0.25968 (10)0.0195 (3)
H21A0.36320.79580.26120.023*
H21B0.49910.79220.27820.023*
C220.42422 (17)0.64578 (16)0.30250 (10)0.0200 (3)
H22A0.43390.66500.35220.024*
H22B0.34930.61030.28970.024*
O110.5614 (5)0.6050 (5)0.4859 (4)0.075 (2)0.5
H110.53130.64210.51440.113*0.5
C230.4943 (5)0.5153 (5)0.4647 (3)0.0330 (10)0.5
H23A0.53030.47390.43030.040*0.5
H23B0.42050.54280.44080.040*0.5
C240.4721 (6)0.4375 (5)0.5187 (3)0.0381 (12)0.5
H24A0.42370.37750.49760.057*0.5
H24B0.54390.40710.54190.057*0.5
H24C0.43380.47610.55240.057*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01251 (8)0.00876 (8)0.01241 (8)−0.00203 (6)0.00167 (6)0.00106 (6)
O10.0144 (5)0.0132 (5)0.0120 (5)−0.0049 (4)0.0007 (4)0.0001 (4)
O20.0200 (6)0.0154 (6)0.0166 (5)−0.0066 (5)−0.0012 (4)0.0027 (4)
O30.0268 (7)0.0157 (6)0.0470 (9)0.0056 (5)0.0229 (7)0.0088 (6)
O40.0363 (9)0.0180 (7)0.0643 (12)0.0118 (6)0.0285 (9)0.0078 (7)
O50.0204 (6)0.0168 (6)0.0290 (7)−0.0020 (5)0.0071 (5)0.0048 (5)
N10.0159 (6)0.0139 (6)0.0152 (6)−0.0031 (5)0.0030 (5)0.0033 (5)
N20.0130 (5)0.0095 (5)0.0195 (6)0.0006 (4)0.0023 (5)0.0017 (5)
N30.0130 (5)0.0102 (5)0.0171 (6)−0.0010 (4)0.0014 (4)0.0004 (4)
N40.0158 (6)0.0142 (6)0.0199 (7)0.0020 (5)0.0035 (5)0.0018 (5)
C10.0117 (6)0.0120 (6)0.0130 (6)−0.0007 (5)0.0004 (5)−0.0010 (5)
C20.0132 (6)0.0112 (6)0.0166 (7)−0.0008 (5)0.0008 (5)−0.0002 (5)
C30.0184 (7)0.0157 (7)0.0197 (7)−0.0034 (6)−0.0005 (6)−0.0035 (6)
C40.0240 (8)0.0250 (9)0.0164 (7)−0.0059 (7)−0.0005 (6)−0.0069 (6)
C50.0233 (8)0.0256 (9)0.0125 (7)−0.0042 (7)0.0000 (6)−0.0030 (6)
C60.0158 (7)0.0168 (7)0.0129 (6)−0.0008 (6)0.0015 (5)0.0005 (5)
C70.0180 (7)0.0207 (8)0.0133 (7)−0.0008 (6)0.0021 (5)0.0038 (6)
C80.0178 (7)0.0185 (8)0.0204 (8)−0.0027 (6)0.0041 (6)0.0083 (6)
C90.0149 (7)0.0115 (7)0.0269 (8)−0.0010 (5)0.0025 (6)0.0065 (6)
C100.0190 (7)0.0114 (7)0.0252 (8)−0.0034 (6)0.0027 (6)−0.0025 (6)
C110.0174 (7)0.0158 (7)0.0191 (7)−0.0033 (6)−0.0021 (6)−0.0022 (6)
Cu20.01411 (9)0.01017 (9)0.01689 (9)0.00239 (7)0.00369 (7)0.00333 (7)
O60.0146 (5)0.0151 (5)0.0137 (5)0.0041 (4)0.0029 (4)0.0019 (4)
O70.0183 (5)0.0145 (5)0.0168 (5)0.0039 (4)0.0042 (4)0.0036 (4)
O80.0142 (5)0.0161 (6)0.0325 (7)0.0015 (4)0.0041 (5)0.0020 (5)
O90.0239 (7)0.0171 (6)0.0378 (8)−0.0061 (5)−0.0012 (6)−0.0051 (6)
O100.0179 (6)0.0173 (6)0.0474 (9)0.0026 (5)0.0076 (6)−0.0077 (6)
N50.0148 (6)0.0118 (6)0.0190 (6)0.0004 (5)0.0007 (5)0.0042 (5)
N60.0143 (6)0.0132 (6)0.0219 (7)0.0009 (5)0.0033 (5)0.0036 (5)
N70.0238 (7)0.0117 (6)0.0195 (7)0.0028 (5)0.0044 (5)0.0010 (5)
N80.0158 (6)0.0139 (6)0.0153 (6)−0.0009 (5)0.0002 (5)0.0014 (5)
C120.0121 (6)0.0111 (6)0.0144 (6)−0.0006 (5)0.0024 (5)0.0006 (5)
C130.0124 (6)0.0113 (6)0.0170 (7)−0.0010 (5)0.0023 (5)0.0005 (5)
C140.0176 (7)0.0123 (7)0.0201 (7)0.0003 (5)0.0042 (6)−0.0018 (5)
C150.0225 (8)0.0190 (8)0.0170 (7)−0.0019 (6)0.0047 (6)−0.0031 (6)
C160.0241 (8)0.0186 (8)0.0148 (7)−0.0013 (6)0.0036 (6)0.0003 (6)
C170.0169 (7)0.0135 (7)0.0158 (7)−0.0010 (5)0.0024 (5)0.0014 (5)
C180.0180 (7)0.0148 (7)0.0155 (7)0.0003 (6)0.0002 (5)0.0041 (5)
C190.0176 (7)0.0141 (7)0.0211 (8)0.0025 (6)0.0006 (6)0.0060 (6)
C200.0204 (8)0.0116 (7)0.0270 (9)0.0017 (6)0.0039 (6)0.0052 (6)
C210.0221 (8)0.0119 (7)0.0250 (8)0.0022 (6)0.0054 (6)−0.0001 (6)
C220.0229 (8)0.0151 (7)0.0239 (8)0.0032 (6)0.0094 (6)0.0020 (6)
O110.073 (4)0.051 (3)0.091 (4)−0.036 (3)−0.019 (3)0.022 (3)
C230.032 (2)0.040 (3)0.027 (2)0.004 (2)0.0071 (18)0.0094 (19)
C240.043 (3)0.029 (3)0.044 (3)−0.003 (2)0.009 (3)0.001 (2)
Geometric parameters (Å, º) top
Cu1—O11.9278 (12)Cu2—O82.3896 (15)
Cu1—N11.9465 (15)O6—C121.316 (2)
Cu1—N22.0020 (15)O7—C131.365 (2)
Cu1—N32.0150 (15)O7—H7A0.8400
Cu1—O32.3286 (15)O8—N81.268 (2)
O1—C11.3200 (19)O9—N81.243 (2)
O2—C21.363 (2)O10—N81.245 (2)
O2—H20.8400N5—C181.280 (2)
O3—N41.257 (2)N5—C191.473 (2)
O4—N41.240 (2)N6—C211.473 (3)
O5—N41.264 (2)N6—C201.473 (2)
N1—C71.280 (2)N6—H61.0000
N1—C81.471 (2)N7—C221.483 (2)
N2—C101.472 (2)N7—H7B0.9100
N2—C91.480 (2)N7—H7C0.9100
N2—H2A1.0000C12—C171.423 (2)
N3—C111.485 (2)C12—C131.423 (2)
N3—H3A0.9100C13—C141.384 (2)
N3—H3B0.9100C14—C151.399 (3)
C1—C61.420 (2)C14—H140.9500
C1—C21.423 (2)C15—C161.378 (3)
C2—C31.383 (2)C15—H150.9500
C3—C41.398 (3)C16—C171.412 (3)
C3—H30.9500C16—H160.9500
C4—C51.373 (3)C17—C181.451 (2)
C4—H40.9500C18—H180.9500
C5—C61.415 (2)C19—C201.519 (3)
C5—H50.9500C19—H19A0.9900
C6—C71.445 (3)C19—H19B0.9900
C7—H70.9500C20—H20A0.9900
C8—C91.520 (3)C20—H20B0.9900
C8—H8A0.9900C21—C221.516 (3)
C8—H8B0.9900C21—H21A0.9900
C9—H9A0.9900C21—H21B0.9900
C9—H9B0.9900C22—H22A0.9900
C10—C111.520 (3)C22—H22B0.9900
C10—H10A0.9900O11—C231.377 (8)
C10—H10B0.9900O11—H110.8400
C11—H11A0.9900C23—C241.471 (8)
C11—H11B0.9900C23—H23A0.9900
Cu2—O61.9295 (12)C23—H23B0.9900
Cu2—N51.9545 (15)C24—H24A0.9800
Cu2—N62.0037 (15)C24—H24B0.9800
Cu2—N72.0043 (16)C24—H24C0.9800
O1—Cu1—N193.69 (6)N5—Cu2—O895.46 (6)
O1—Cu1—N2173.40 (6)N6—Cu2—O8108.03 (6)
N1—Cu1—N283.95 (6)N7—Cu2—O896.76 (6)
O1—Cu1—N395.47 (5)C12—O6—Cu2122.90 (11)
N1—Cu1—N3163.61 (6)C13—O7—H7A109.5
N2—Cu1—N385.43 (6)N8—O8—Cu2119.86 (11)
O1—Cu1—O391.72 (6)C18—N5—C19120.75 (15)
N1—Cu1—O3103.45 (6)C18—N5—Cu2125.32 (12)
N2—Cu1—O394.83 (6)C19—N5—Cu2113.56 (12)
N3—Cu1—O389.85 (6)C21—N6—C20116.27 (15)
C1—O1—Cu1125.08 (10)C21—N6—Cu2108.52 (11)
C2—O2—H2109.5C20—N6—Cu2106.46 (11)
N4—O3—Cu1125.24 (12)C21—N6—H6108.5
C7—N1—C8119.95 (15)C20—N6—H6108.5
C7—N1—Cu1126.66 (12)Cu2—N6—H6108.5
C8—N1—Cu1113.35 (11)C22—N7—Cu2108.93 (12)
C10—N2—C9116.22 (14)C22—N7—H7B109.9
C10—N2—Cu1108.75 (11)Cu2—N7—H7B109.9
C9—N2—Cu1107.70 (10)C22—N7—H7C109.9
C10—N2—H2A108.0Cu2—N7—H7C109.9
C9—N2—H2A108.0H7B—N7—H7C108.3
Cu1—N2—H2A108.0O9—N8—O10120.82 (16)
C11—N3—Cu1107.84 (11)O9—N8—O8120.08 (16)
C11—N3—H3A110.1O10—N8—O8119.09 (15)
Cu1—N3—H3A110.1O6—C12—C17125.50 (15)
C11—N3—H3B110.1O6—C12—C13117.21 (14)
Cu1—N3—H3B110.1C17—C12—C13117.29 (15)
H3A—N3—H3B108.5O7—C13—C14118.69 (15)
O4—N4—O3119.83 (16)O7—C13—C12120.07 (15)
O4—N4—O5120.90 (16)C14—C13—C12121.23 (15)
O3—N4—O5119.17 (15)C13—C14—C15120.82 (16)
O1—C1—C6125.26 (15)C13—C14—H14119.6
O1—C1—C2117.61 (14)C15—C14—H14119.6
C6—C1—C2117.13 (14)C16—C15—C14119.37 (17)
O2—C2—C3118.38 (15)C16—C15—H15120.3
O2—C2—C1120.37 (14)C14—C15—H15120.3
C3—C2—C1121.24 (16)C15—C16—C17121.17 (17)
C2—C3—C4120.84 (17)C15—C16—H16119.4
C2—C3—H3119.6C17—C16—H16119.4
C4—C3—H3119.6C16—C17—C12120.10 (16)
C5—C4—C3119.50 (17)C16—C17—C18117.12 (16)
C5—C4—H4120.3C12—C17—C18122.78 (16)
C3—C4—H4120.3N5—C18—C17124.45 (16)
C4—C5—C6120.99 (17)N5—C18—H18117.8
C4—C5—H5119.5C17—C18—H18117.8
C6—C5—H5119.5N5—C19—C20107.15 (14)
C5—C6—C1120.29 (16)N5—C19—H19A110.3
C5—C6—C7116.37 (16)C20—C19—H19A110.3
C1—C6—C7123.34 (15)N5—C19—H19B110.3
N1—C7—C6124.67 (16)C20—C19—H19B110.3
N1—C7—H7117.7H19A—C19—H19B108.5
C6—C7—H7117.7N6—C20—C19107.61 (15)
N1—C8—C9107.75 (14)N6—C20—H20A110.2
N1—C8—H8A110.2C19—C20—H20A110.2
C9—C8—H8A110.2N6—C20—H20B110.2
N1—C8—H8B110.2C19—C20—H20B110.2
C9—C8—H8B110.2H20A—C20—H20B108.5
H8A—C8—H8B108.5N6—C21—C22107.86 (15)
N2—C9—C8106.64 (14)N6—C21—H21A110.1
N2—C9—H9A110.4C22—C21—H21A110.1
C8—C9—H9A110.4N6—C21—H21B110.1
N2—C9—H9B110.4C22—C21—H21B110.1
C8—C9—H9B110.4H21A—C21—H21B108.4
H9A—C9—H9B108.6N7—C22—C21108.72 (15)
N2—C10—C11107.39 (14)N7—C22—H22A109.9
N2—C10—H10A110.2C21—C22—H22A109.9
C11—C10—H10A110.2N7—C22—H22B109.9
N2—C10—H10B110.2C21—C22—H22B109.9
C11—C10—H10B110.2H22A—C22—H22B108.3
H10A—C10—H10B108.5C23—O11—H11109.5
N3—C11—C10108.50 (14)O11—C23—C24116.9 (6)
N3—C11—H11A110.0O11—C23—H23A108.1
C10—C11—H11A110.0C24—C23—H23A108.1
N3—C11—H11B110.0O11—C23—H23B108.1
C10—C11—H11B110.0C24—C23—H23B108.1
H11A—C11—H11B108.4H23A—C23—H23B107.3
O6—Cu2—N593.08 (6)C23—C24—H24A109.5
O6—Cu2—N6167.90 (6)C23—C24—H24B109.5
N5—Cu2—N683.82 (6)H24A—C24—H24B109.5
O6—Cu2—N795.58 (6)C23—C24—H24C109.5
N5—Cu2—N7165.70 (6)H24A—C24—H24C109.5
N6—Cu2—N785.36 (6)H24B—C24—H24C109.5
O6—Cu2—O883.87 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.842.282.7243 (18)114
O2—H2···O60.841.932.6969 (18)151
N2—H2A···O51.002.132.968 (2)140
N2—H2A···O10i1.002.293.017 (2)129
N3—H3A···O80.912.253.126 (2)162
N3—H3B···O2ii0.912.363.138 (2)143
N3—H3B···O70.912.473.071 (2)124
O7—H7A···O10.841.982.7365 (18)150
O7—H7A···O60.842.262.7096 (18)114
N6—H6···O5iii1.002.102.960 (2)143
N6—H6···O101.002.343.067 (2)129
N7—H7B···O30.912.042.932 (2)167
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.842.282.7243 (18)113.6
O2—H2···O60.841.932.6969 (18)150.7
N2—H2A···O51.002.132.968 (2)140.1
N2—H2A···O10i1.002.293.017 (2)129.0
N3—H3A···O80.912.253.126 (2)161.7
N3—H3B···O2ii0.912.363.138 (2)143.2
N3—H3B···O70.912.473.071 (2)124.0
O7—H7A···O10.841.982.7365 (18)149.7
O7—H7A···O60.842.262.7096 (18)113.7
N6—H6···O5iii1.002.102.960 (2)142.8
N6—H6···O101.002.343.067 (2)129.1
N7—H7B···O30.912.042.932 (2)167.4
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.
 

Acknowledgements

This work was supported by grants from the Department of Science and Technology, SERB, New Delhi, India (SERB/F/815/2014–15). SN thanks the Chairman of the Department of Chemistry, Aligarh Muslim University, India, who facilitated this research.

References

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages m205-m206
https://doi.org/10.1107/S205698901501960X
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