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The structure of the title compound, [Cu2(C12H24N4O2)(C3H4N2)2(CH4O)2](ClO4)2 or [Cu2(dmoxpn)(HIm)2(CH3OH)2](ClO4)2, where dmoxpn is the dianion of N,N'-bis­[3-(dimethyl­amino)prop­yl]oxamide and HIm is imidazole, consists of a centrosymmetric trans-oxamidate-bridged copper(II) binuclear cation, having an inversion centre at the mid-point of the central C-C bond, and two perchlorate anions. The CuII atom has square-pyramidal coordination geometry involving two N atoms and an O atom from the dmoxpn ligand, an N atom from an imidazole ring, and an O atom from a methanol mol­ecule. The crystal structure is stabilized by O-H...O, N-H...O and C-H...O hydrogen bonds and imidazole [pi]-[pi] stacking inter­actions to form a three-dimensional supra­molecular array.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106042624/sq3043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106042624/sq3043Isup2.hkl
Contains datablock I

CCDC reference: 632917

Comment top

Many studies have been devoted to the development of synthetic strategies for the architecture of coordination metal supramolecules (Hoskins & Robson, 1990; Black et al., 1996; Funeriu et al., 1997). A successful strategy leading to three-dimensional supramolecular systems is to utilize the ππ stacking of aromatic groups and/or the hydrogen bonding of coordinated ligands in addition to their coordination capability to interlink zero-, one- or two-dimensional coordination molecules (Chen et al., 1998; Yi et al., 2004). As is well known, N,N'-disubstituted oxamidate has proven to give rise to three-dimensional supramolecular structures because of the easy cistrans conformational change, the flexible binding mode, and the ability to form hydrogen bonds (Chen et al., 1998). On the other hand, imidazole is a suitable ligand in the construction of supramolecular frameworks owing to the strong tendency to form ππ stacking and hydrogen bonds (Chen et al., 1994; Zhang et al., 1999). To our knowledge, only three crystal structures of oxamidate-bridged binuclear metal complexes containing an imidazole ligand have been characterized, viz. Cu2(oxpn)(HIm)2(NO3)2, A (Zhang et al., 1999), [Cu2(oxpn)(HIm)2(H2O)2](ClO4)2, B (Chen et al., 1994), and Cu2(oxen)(HIm)2, C (Li et al., 2004), where oxpn is deprotonated N,N'-bis(3-aminopropyl)oxamide and oxen is deprotonated N,N'-bis(3-aminoethyl)oxamide. However, the hydrogen bonds in these complexes were not discussed in detail and the ππ stacking of the imidazole groups was not studied at all. In order to obtain more information on supramolecular architecture constructed by hydrogen bonds and π-π stacking interactions in this kind of complex, we chose N,N'-bis[3-(dimethylamino)propyl]oxamide (H2dmoxpn) as the bridging ligand and imidazole as a terminal ligand to synthesize a binuclear copper(II) complex formulated as Cu2(dmoxpn)(HIm)2(CH3OH)2(ClO4)2 (I).

The molecular structure of (I), as shown in Fig. 1, consists of centrosymmetric dinuclear copper(II) cations bridged by dmoxpn2− anions, each CuII atom coordinating two imidazole and two methanol molecules, and two perchlorate counter-anions. The Cu···Cu separation through the oxamido bridge is 5.2824 (13) Å. The cation has a transoid conformation and occupies a special inversion center at the middle of the C6—C6i bond [symmetry code: (i) −x, −y, −z] which is the same as in the other three examples of oxamide complexes AC. In contrast to the ligands oxpn and oxen, the dmoxpn ligand can only adopt a trans conformation when it coordinates to metal ions owing to the steric hindrance induced by the presence of methyl substituents on the amine groups (Ruiz et al., 1999; Lloret et al., 1992). The coordination environment of the copper(II) atom in (I) is a square pyramid, with the coordinated methanol molecule and perchlorate ion in axial sites to form a [4 + 2] quasi-octahedral geometry. The CuII atom is displaced 0.0751 (17) Å out of the basal plane. The axial Cu···O distances of 2.616 (4) Å (Cu1—O2) and 2.851 (4) Å (Cu1···O3) are significantly longer than those in the equatorial plane (Table 1). The imidazole ring is nearly perpendicular to the coordination plane, with a dihedral angle of 75.67 (14)°, which is very similar to the value of 78.6° in compound B with the same [4 + 2] quasi-octahedral coordination geometry, whereas with a much elongated [4 + 1] square–pyramidal geometry, approximately parallel angles of 15.30° and 27° are found in compounds A and C, respectively.

The bis-tridentate dmoxpn ligand produces five- and six-membered chelate rings. The bite angles are 82.95 (11) and 97.01 (12)°, respectively. The five-membered ring has an envelope conformation, while the six-membered ring is intermediate between half-boat and twist-boat conformations; the corresponding puckering parameters (Cremer & Pople, 1975) are ϕ = 180 (2)°, Q = 0.096 (3) Å and θ = 121.5 (4)°, and ϕ = 341.4 (5)° and Q = 0.550 (5) Å, respectively. The oxamide bridge is planar within experimental uncertainties. The dihedral angle between the oxamide bridge and the coordination plane is 10.48 (6)°. The C6—N2 and C6—C6i distances of 1.299 (5) and 1.492 (7) Å are typical CN and Csp2—Csp2 values, respectively. Given that the C6—O1 distance of 1.282 (4) Å is in accordance with those of (Oδb)C—O fragments in many examples (Delgado et al., 2006; Berg et al., 2002; Nash & Schaefer, 1969), the oxamido is best described as NC—O rather than delocalized.

The perchlorate anions stabilize the crystal structure by hydrogen bonds with methanol and HIm ligands (Table 2). As illustrated in Fig. 2, the perchlorate anions bridge the dinuclear copper(II) cationic complexes to form a two-dimensional hydrogen-bonding network parallel to the (101) crystal plane. Owing to the substitution of the H atoms of the primary amine of oxpn by methyl groups, the dmoxpn ligand does not participate in any hydrogen bonding, which is different from the oxpn or oxen in compounds AC. By contrast, the HIm ligand contributes to not only the hydrogen bonds but also the ππ stacking interactions. Along the a axial direction, the complexes are assembled by N4—H4···O1ii hydrogen bonds [symmetry code: (ii) 1 + x, y, z] and the stacking between the aromatic rings of HIm and HImvi [symmetry code: (vi) 1 − x, −y, −z] (Fig. 3). The nearest separation is 3.092 (6) Å (C8···C8vi). This parallel edge-edge ππ stacking is also found in compounds A (3.282 Å) and B (3.097 Å). The separations of A and B were calculated according to the data in the Cambridge Structural Database (Allen, 2002).

Experimental top

The ligand H2dmoxpn was prepared by using the reported method (Ojima & Yamada, 1970). An ethanol solution (5 ml) of copper(II) perchlorate hexahydrate (0.2 mmol, 0.0741 g) was added slowly to an ethanol solution (5 ml) containing H2dmoxpn (0.1 mmol, 0.0258 g) and piperidine (0.2 mmol, 0.017 g). The mixture was stirred quickly for 30 minutes, then a methanol solution (5 ml) of imidazole (0.2 mmol, 0.0136 g) was added dropwise to the mixture. The reaction solution was heated at 333 K with stirring for 6 h. The resulting solution was filtered and concentrated by slow evaporation at room temperature for several days, and then dark-blue crystals (yield 0.0477 g, 61%) of the compound suitable for X-ray analysis were obtained from the solution.

Refinement top

The hydroxy H atoms of the methanol molecules were located in a difference Fouier map and refined in a riding model (O—H = 0.98 Å) [Uiso treatment for this atom?]. The other H atoms were positioned geometrically, with an N—H distance of 0.86 Å and C—H distances of 0.93 Å (Csp2—H), 0.97 Å (CH2) and 0.96 Å (CH3), and were then treated as riding with Uiso(H) values of 1.2Ueq(C,N) and 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids. [Symmetry code: (i) −x, −y, −z.]
[Figure 2] Fig. 2. The two-dimensional hydrogen-bonded structure parallel to the (101) plane. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) −x, −y, −z; (iii) 1/2 + x, 1/2 − y, −1/2 + z; (iv) −1/2 + x, 1/2 − y, 1/2 + z; (v) x, y + 1, z.]
[Figure 3] Fig. 3. The packing of (I), showing ππ stacking interactions between imidazole groups and a one-dimensional hydrogen bonding structure along a axis. Dashed lines indicate hydrogen bonds and the ππ interaction. [Symmetry codes: (i) −x, −y, −z; (ii) 1 + x, y, z; (vi) 1 − x, −y, −z.]
{µ-N,N'-Bis[3-(dimethylamino)propyl]oxamidato(2-)- κ6N,N',O':N'',N''',O}bis[(1H-imidazole-κN3)(methanol-κO)copper(II)] bis(perchlorate) top
Crystal data top
[Cu2(C12H24N4O2)(C3H4N2)2(CH4O)2](ClO4)2F(000) = 808
Mr = 782.60Dx = 1.647 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2584 reflections
a = 10.023 (3) Åθ = 2.6–27.8°
b = 13.084 (3) ŵ = 1.59 mm1
c = 12.317 (3) ÅT = 298 K
β = 102.328 (4)°Block, dark blue
V = 1578.0 (7) Å30.50 × 0.14 × 0.09 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
3121 independent reflections
Radiation source: fine-focus sealed tube2201 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 26.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1212
Tmin = 0.504, Tmax = 0.870k = 1516
8761 measured reflectionsl = 915
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0512P)2 + 1.6075P]
where P = (Fo2 + 2Fc2)/3
3121 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
[Cu2(C12H24N4O2)(C3H4N2)2(CH4O)2](ClO4)2V = 1578.0 (7) Å3
Mr = 782.60Z = 2
Monoclinic, P21/nMo Kα radiation
a = 10.023 (3) ŵ = 1.59 mm1
b = 13.084 (3) ÅT = 298 K
c = 12.317 (3) Å0.50 × 0.14 × 0.09 mm
β = 102.328 (4)°
Data collection top
Bruker APEX area-detector
diffractometer
3121 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2201 reflections with I > 2σ(I)
Tmin = 0.504, Tmax = 0.870Rint = 0.042
8761 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.04Δρmax = 0.54 e Å3
3121 reflectionsΔρmin = 0.33 e Å3
203 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
xyzUiso*/Ueq
C10.2616 (6)0.3469 (4)0.0329 (5)0.0623 (14)
H1A0.26970.41930.02090.093*
H1B0.20440.33360.10450.093*
H1C0.35040.31800.02960.093*
C20.2874 (5)0.3248 (4)0.1634 (4)0.0590 (13)
H2A0.37990.30520.16430.089*
H2B0.25520.28820.22040.089*
H2C0.28360.39690.17670.089*
C30.0653 (5)0.3491 (3)0.0559 (5)0.0568 (13)
H3A0.04240.33410.12680.068*
H3B0.07570.42270.05160.068*
C40.0506 (5)0.3170 (4)0.0339 (5)0.0588 (14)
H4A0.01940.31400.10320.071*
H4B0.12140.36870.04220.071*
C50.1120 (4)0.2155 (3)0.0152 (4)0.0388 (10)
H5A0.14810.21870.05180.047*
H5B0.18710.20060.07710.047*
C60.0540 (3)0.0401 (3)0.0059 (3)0.0279 (8)
C70.1968 (6)0.1677 (5)0.2865 (5)0.0837 (19)
H7A0.13780.22490.31020.126*
H7B0.17770.11460.34140.126*
H7C0.29020.18880.27750.126*
C80.4833 (4)0.1298 (3)0.0125 (4)0.0410 (10)
H80.46970.15720.05870.049*
C90.5817 (4)0.0574 (4)0.1675 (4)0.0498 (12)
H90.64650.02640.22300.060*
C100.4510 (4)0.0777 (3)0.1705 (4)0.0438 (10)
H100.40940.06280.22920.053*
N10.2003 (3)0.3002 (3)0.0540 (3)0.0408 (9)
N20.0104 (3)0.1337 (2)0.0044 (3)0.0301 (7)
N30.3891 (3)0.1240 (2)0.0729 (3)0.0357 (8)
N40.6003 (3)0.0906 (3)0.0685 (3)0.0486 (10)
H40.67520.08720.04530.058*
O10.1776 (2)0.00981 (19)0.0161 (2)0.0338 (6)
O20.1744 (4)0.1308 (3)0.1849 (3)0.0718 (11)
H20.10200.08140.21220.09 (2)*
O30.1643 (4)0.0997 (3)0.2507 (3)0.0724 (11)
O40.0299 (5)0.2255 (3)0.3026 (4)0.0907 (13)
O50.0946 (5)0.0904 (4)0.4181 (3)0.1060 (16)
O60.0636 (4)0.0703 (4)0.2521 (4)0.1058 (16)
Cl10.05644 (11)0.12021 (8)0.30697 (9)0.0456 (3)
Cu10.18881 (4)0.14413 (3)0.02921 (4)0.03355 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.075 (3)0.044 (3)0.076 (4)0.006 (2)0.034 (3)0.009 (3)
C20.058 (3)0.048 (3)0.070 (4)0.007 (2)0.012 (3)0.009 (2)
C30.047 (3)0.034 (2)0.090 (4)0.004 (2)0.017 (3)0.003 (2)
C40.043 (3)0.038 (3)0.093 (4)0.005 (2)0.009 (3)0.010 (3)
C50.026 (2)0.038 (2)0.053 (3)0.0053 (17)0.0111 (18)0.0005 (19)
C60.0199 (17)0.034 (2)0.032 (2)0.0003 (15)0.0100 (15)0.0002 (16)
C70.074 (4)0.082 (4)0.100 (5)0.008 (3)0.032 (3)0.040 (4)
C80.034 (2)0.040 (2)0.055 (3)0.0084 (18)0.0224 (19)0.006 (2)
C90.035 (2)0.057 (3)0.055 (3)0.010 (2)0.002 (2)0.009 (2)
C100.037 (2)0.053 (3)0.043 (3)0.004 (2)0.0119 (19)0.007 (2)
N10.0342 (18)0.0344 (19)0.056 (2)0.0044 (14)0.0143 (17)0.0009 (16)
N20.0202 (14)0.0300 (17)0.0423 (19)0.0032 (12)0.0113 (13)0.0014 (14)
N30.0217 (15)0.0376 (19)0.050 (2)0.0028 (13)0.0112 (14)0.0080 (16)
N40.0227 (17)0.048 (2)0.079 (3)0.0054 (15)0.0206 (18)0.020 (2)
O10.0204 (13)0.0320 (14)0.0509 (18)0.0022 (10)0.0122 (11)0.0019 (12)
O20.084 (3)0.074 (3)0.064 (2)0.020 (2)0.031 (2)0.0002 (19)
O30.057 (2)0.099 (3)0.071 (2)0.020 (2)0.0356 (18)0.002 (2)
O40.111 (3)0.060 (2)0.118 (4)0.017 (2)0.063 (3)0.001 (2)
O50.104 (3)0.157 (5)0.064 (3)0.043 (3)0.032 (2)0.038 (3)
O60.071 (3)0.128 (4)0.123 (4)0.044 (3)0.030 (3)0.039 (3)
Cl10.0407 (6)0.0505 (7)0.0487 (7)0.0033 (5)0.0160 (5)0.0001 (5)
Cu10.0206 (2)0.0305 (3)0.0514 (3)0.00154 (19)0.01192 (19)0.0026 (2)
Geometric parameters (Å, º) top
Cu1—N12.064 (3)C6—N21.299 (5)
Cu1—N21.955 (3)C6—O11.282 (4)
Cu1—N31.982 (3)C6—C6i1.492 (7)
Cu1—O1i2.022 (3)C7—O21.403 (7)
C1—N11.475 (6)C7—H7A0.9600
C1—H1A0.9600C7—H7B0.9600
C1—H1B0.9600C7—H7C0.9600
C1—H1C0.9600C8—N31.323 (5)
C2—N11.477 (6)C8—N41.329 (5)
C2—H2A0.9600C8—H80.9300
C2—H2B0.9600C9—C101.344 (6)
C2—H2C0.9600C9—N41.345 (6)
C3—C41.484 (7)C9—H90.9300
C3—N11.501 (5)C10—N31.371 (5)
C3—H3A0.9700C10—H100.9300
C3—H3B0.9700N4—H40.8600
C4—C51.502 (6)O2—H20.9767
C4—H4A0.9700O3—Cl11.429 (3)
C4—H4B0.9700O4—Cl11.402 (4)
C5—N21.463 (5)O5—Cl11.396 (4)
C5—H5A0.9700O6—Cl11.408 (4)
C5—H5B0.9700
N1—Cu1—N297.01 (12)C3—C4—C5114.7 (4)
N1—Cu1—N394.04 (13)C3—C4—H4A108.6
N1—Cu1—O1i176.09 (13)C3—C4—H4B108.6
N2—Cu1—N3167.84 (13)C5—C4—H4A108.6
N2—Cu1—O1i82.95 (11)C5—C4—H4B108.6
N3—Cu1—O1i85.68 (11)H4A—C4—H4B107.6
C1—N1—C2108.4 (4)N2—C5—C4111.1 (3)
C1—N1—C3110.5 (4)N2—C5—H5A109.4
C1—N1—Cu1108.7 (3)N2—C5—H5B109.4
C2—N1—C3104.5 (4)C4—C5—H5A109.4
C2—N1—Cu1110.7 (3)C4—C5—H5B109.4
C3—N1—Cu1113.8 (2)H5A—C5—H5B108.0
C5—N2—C6117.6 (3)N2—C6—C6i115.3 (4)
C5—N2—Cu1128.9 (2)N2—C6—O1127.4 (3)
C6—N2—Cu1113.2 (2)O1—C6—C6i117.2 (4)
C8—N3—C10105.9 (3)O2—C7—H7A109.5
C8—N3—Cu1130.0 (3)O2—C7—H7B109.5
C10—N3—Cu1122.6 (3)O2—C7—H7C109.5
C8—N4—C9108.5 (3)H7A—C7—H7B109.5
C8—N4—H4125.7H7A—C7—H7C109.5
C9—N4—H4125.7H7B—C7—H7C109.5
N1—C1—H1A109.5N3—C8—N4110.0 (4)
N1—C1—H1B109.5N3—C8—H8125.0
N1—C1—H1C109.5N4—C8—H8125.0
H1A—C1—H1B109.5N4—C9—C10106.6 (4)
H1A—C1—H1C109.5N4—C9—H9126.7
H1B—C1—H1C109.5C10—C9—H9126.7
N1—C2—H2A109.5N3—C10—C9108.9 (4)
N1—C2—H2B109.5N3—C10—H10125.5
N1—C2—H2C109.5C9—C10—H10125.5
H2A—C2—H2B109.5C6—O1—Cu1i110.6 (2)
H2A—C2—H2C109.5C7—O2—H299.8
H2B—C2—H2C109.5O3—Cl1—O4108.9 (2)
N1—C3—H3A108.4O3—Cl1—O5110.2 (2)
N1—C3—H3B108.4O3—Cl1—O6109.7 (3)
N1—C3—C4115.6 (4)O4—Cl1—O5108.8 (3)
C4—C3—H3A108.4O4—Cl1—O6107.5 (3)
C4—C3—H3B108.4O5—Cl1—O6111.6 (3)
H3A—C3—H3B107.5
N1—C3—C4—C579.1 (6)C6i—C6—O1—Cu1i6.0 (5)
C3—C4—C5—N259.5 (6)C6—N2—Cu1—N313.5 (8)
N3—C8—N4—C90.7 (5)C5—N2—Cu1—N3159.2 (6)
C8—N4—C9—C100.3 (5)C6—N2—Cu1—O1i7.4 (3)
N4—C9—C10—N30.2 (5)C5—N2—Cu1—O1i180.0 (3)
C4—C3—N1—C176.8 (5)C6—N2—Cu1—N1168.7 (3)
C4—C3—N1—C2166.8 (4)C5—N2—Cu1—N14.0 (3)
C4—C3—N1—Cu145.9 (5)C8—N3—Cu1—N2117.9 (7)
O1—C6—N2—C50.2 (6)C10—N3—Cu1—N246.6 (8)
C6i—C6—N2—C5179.8 (4)C8—N3—Cu1—O1i97.1 (3)
O1—C6—N2—Cu1173.7 (3)C10—N3—Cu1—O1i67.4 (3)
C6i—C6—N2—Cu16.3 (5)C8—N3—Cu1—N186.8 (3)
C4—C5—N2—C6169.1 (4)C10—N3—Cu1—N1108.7 (3)
C4—C5—N2—Cu118.5 (5)C1—N1—Cu1—N2115.2 (3)
N4—C8—N3—C100.8 (4)C2—N1—Cu1—N2125.8 (3)
N4—C8—N3—Cu1167.3 (3)C3—N1—Cu1—N28.4 (3)
C9—C10—N3—C80.6 (5)C1—N1—Cu1—N369.8 (3)
C9—C10—N3—Cu1168.3 (3)C2—N1—Cu1—N349.1 (3)
N2—C6—O1—Cu1i174.0 (3)C3—N1—Cu1—N3166.5 (3)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O6i0.982.062.907 (6)144
N4—H4···O1ii0.862.062.855 (4)153
C8—H8···O4iii0.932.473.317 (6)152
Symmetry codes: (i) x, y, z; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formula[Cu2(C12H24N4O2)(C3H4N2)2(CH4O)2](ClO4)2
Mr782.60
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.023 (3), 13.084 (3), 12.317 (3)
β (°) 102.328 (4)
V3)1578.0 (7)
Z2
Radiation typeMo Kα
µ (mm1)1.59
Crystal size (mm)0.50 × 0.14 × 0.09
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.504, 0.870
No. of measured, independent and
observed [I > 2σ(I)] reflections
8761, 3121, 2201
Rint0.042
(sin θ/λ)max1)0.620
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.117, 1.04
No. of reflections3121
No. of parameters203
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.33

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Cu1—N12.064 (3)C5—N21.463 (5)
Cu1—N21.955 (3)C6—N21.299 (5)
Cu1—N31.982 (3)C6—O11.282 (4)
Cu1—O1i2.022 (3)C6—C6i1.492 (7)
N1—Cu1—N297.01 (12)N3—Cu1—O1i85.68 (11)
N1—Cu1—N394.04 (13)C5—N2—C6117.6 (3)
N1—Cu1—O1i176.09 (13)C5—N2—Cu1128.9 (2)
N2—Cu1—N3167.84 (13)C6—N2—Cu1113.2 (2)
N2—Cu1—O1i82.95 (11)C6—O1—Cu1i110.6 (2)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O6i0.982.062.907 (6)143.8
N4—H4···O1ii0.862.062.855 (4)153.1
C8—H8···O4iii0.932.473.317 (6)152.3
Symmetry codes: (i) x, y, z; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z1/2.
 

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