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Acta Cryst. (2007). E63, m1692-m1693    [ doi:10.1107/S1600536807023082 ]

catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline)copper(II)]-[mu]-benzene-1,3-dicarboxylato] N,N-dimethylacetamide monohydrate]

W.-Z. Zhang

Abstract top

In the title compound, [Cu(C8H4O4)(C14H8N4)(H2O)]·C4H9NO·H2O, the CuII atom is five-coordinated by three O atoms from two benzene-1,3-dicarboxylate (1,3-bdc) ligands and one water molecule, and two N atoms from one chelating pyrazino[2,3-f][1,10]phenanthroline (L) ligand in a distorted square-pyramidal geometry. The CuII atoms are bridged by the 1,3-bdc ligands to form a one-dimensional helical chain structure. A network of O-H...O hydrogen bonds completes the structure. There are two half-molecules of 1,3-bdc in the asymmetric unit; both complete molecules are generated by twofold rotation symmetry, with two C atoms lying on the rotation axis in each case.

Comment top

Recently, helical structures have received intense interest in coordination chemistry (Cai et al., 2006). It is well known that a bidentate organic acid ligand may be useful in the formation of helical chains in the presence of 2,2'-bipyridine (bipy) or 1,10-phenanthroline (phen). The N atoms from the bipy or phen ligand may occupy two coordination positions of central metals (Ren & Zhao, 2006). The additional coordination positions are available for the bidentate carboxylate ligands, leading to the formation of a helix (Yang et al., 2005).

We therefore selected benzene-1,3-dicarboxylic acid (1,3-bdcH2) as a bridging ligand and pyrazino[2,3-f][1,10]phenanthroline (L) as a secondary ligand, forming a the title compound, (I), a new helical Cu(II) coordination polymer, [Cu(1,3-bdc)(L)(H2O].DMA.H2O (DMA = N,N-dimethylacetamide), which is reported here.

Selected bond lengths and angles for (I) are given in Table 1. In (I) each CuII atom is five-coordinated by three O atoms from two monodentate 1,3-bdc ligands and one water molecule, and two N atoms from one chelating L ligand in a distorted square-pyramidal coordination sphere (Fig. 1). Two carboxylate O atoms (O2, O3) and two N atoms (N1, N2) form the equatorial plane, whereas the water molecule occupies the axial position with Cu1—O1w distance of 2.324 (4) Å.

The 1,3-bdc ligands linked the CuII atoms to form a one-dimensional helical chain structure (Fig. 2). The helical chain is decorated with L ligands, alternately at each side. Finally, O—H···O H-bonds complete the structure of (I) (Table 2).

Related literature top

One related helical coordination polymer, [Cu(1,4-bdc)(L)(H2O)], where 1,4-bdc is the benzene-1,4-dicarboxylate dianion, has been reported. In this compound, the CuII atom is five-coordinated and exhibits a distorted square-pyramidal coordination environment. The CuII atoms are bridged by the 1,4-bdc ligands to form a one-dimensional helical chain structure (Zhang et al., 2007).

For related literature, see: Cai et al. (2006); Dickeson & Summers (1970); Ren & Zhao (2006); Yang et al. (2005).

Experimental top

The L ligand was synthesized according to the literature method (Dickeson & Summers, 1970). A N,N-dimethylacetamide solution (15 ml) of L (121 mg, 0.5 mmol) was mixed with an aqueous solution (6 ml) of ClCl2.2H2O (86 mg, 0.5 mmol) with stirring at 385 K. Then the 1,3-bdcH2 was added to the mixture with stirring. The resulting solution was filtered, the filtrate was allowed to stand in air at room temperature for two weeks, and blue crystals of (I) were obtained (yield 29% based on Cu).

Refinement top

All H atoms on C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier). The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85 (1) Å; Uiso was allowed to refine freely.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms). Symmetry codes: (i) 1 - x, y, 3/2 - z; (ii) -x, y, 3/2 - z.
[Figure 2] Fig. 2. View of part of the helical chain structure of (I) with DMA and uncoordinated water molecules omitted for clarity.
catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline)copper(II)]-µ- benzene-1,3-dicarboxylato] N,N-dimethylacetamide monohydrate] top
Crystal data top
[Cu(C8H4O4)(C14H8N4)(H2O)]·C4H9NO·H2OF(000) = 1204
Mr = 583.05Dx = 1.516 Mg m−3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 17473 reflections
a = 14.829 (3) Åθ = 3.2–27.5°
b = 7.2111 (14) ŵ = 0.91 mm−1
c = 23.976 (5) ÅT = 293 K
β = 95.00 (3)°Block, blue
V = 2554.1 (9) Å30.33 × 0.31 × 0.30 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5813 independent reflections
Radiation source: rotating anode4102 reflections with I > 2σ(I)
graphiteRint = 0.061
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −19→18
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −9→9
Tmin = 0.733, Tmax = 0.766l = −31→31
23862 measured reflections
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0676P)2 + 7.6293P]
where P = (Fo2 + 2Fc2)/3
5813 reflections(Δ/σ)max < 0.001
373 parametersΔρmax = 1.09 e Å−3
7 restraintsΔρmin = −0.43 e Å−3
Crystal data top
[Cu(C8H4O4)(C14H8N4)(H2O)]·C4H9NO·H2OV = 2554.1 (9) Å3
Mr = 583.05Z = 4
Monoclinic, P2/cMo Kα radiation
a = 14.829 (3) ŵ = 0.91 mm−1
b = 7.2111 (14) ÅT = 293 K
c = 23.976 (5) Å0.33 × 0.31 × 0.30 mm
β = 95.00 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5813 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4102 reflections with I > 2σ(I)
Tmin = 0.733, Tmax = 0.766Rint = 0.061
23862 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.068H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.184Δρmax = 1.09 e Å−3
S = 1.07Δρmin = −0.43 e Å−3
5813 reflectionsAbsolute structure: ?
373 parametersFlack parameter: ?
7 restraintsRogers parameter: ?
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
C10.4129 (3)0.2052 (8)0.5417 (2)0.0440 (12)
H10.43760.15900.57590.053*
C20.4719 (3)0.2530 (8)0.5017 (2)0.0497 (13)
H20.53420.24290.50970.060*
C30.4370 (3)0.3140 (7)0.4510 (2)0.0440 (11)
H30.47520.34320.42350.053*
C40.3426 (3)0.3333 (6)0.43985 (18)0.0357 (10)
C50.2887 (3)0.2852 (6)0.48253 (17)0.0314 (9)
C60.1916 (3)0.2943 (6)0.47436 (17)0.0297 (9)
C70.0563 (3)0.2370 (7)0.5113 (2)0.0424 (11)
H70.02460.19830.54110.051*
C80.0072 (3)0.2930 (8)0.4617 (2)0.0475 (12)
H8−0.05580.29090.45870.057*
C90.0525 (3)0.3505 (7)0.4178 (2)0.0422 (11)
H90.02080.38790.38450.051*
C100.1472 (3)0.3528 (6)0.42319 (18)0.0339 (9)
C110.2981 (3)0.3891 (6)0.38611 (18)0.0376 (10)
C120.2044 (3)0.4006 (6)0.37806 (17)0.0346 (10)
C130.2132 (4)0.4844 (7)0.2878 (2)0.0522 (14)
H130.18630.51860.25280.063*
C140.3063 (5)0.4713 (8)0.2957 (2)0.0570 (15)
H140.33950.49410.26520.068*
C150.3677 (3)0.1853 (8)0.67698 (17)0.0414 (12)
C160.4361 (3)0.0762 (7)0.71521 (17)0.0361 (10)
C170.50000.1725 (9)0.75000.0340 (13)
H170.50000.30150.75000.041*
C180.4360 (3)−0.1149 (8)0.7155 (2)0.0456 (12)
H180.3931−0.17980.69250.055*
C190.5000−0.2104 (12)0.75000.058 (2)
H190.5000−0.33940.75000.070*
C200.0931 (3)0.2029 (7)0.66650 (17)0.0352 (10)
C210.0441 (3)0.0973 (6)0.70954 (16)0.0319 (9)
C220.00000.1949 (9)0.75000.0318 (13)
H220.00000.32390.75000.038*
C230.0432 (3)−0.0947 (7)0.71019 (19)0.0407 (11)
H230.0721−0.15970.68340.049*
C240.0000−0.1916 (10)0.75000.0461 (17)
H240.0000−0.32060.75000.055*
C250.2265 (4)−0.0370 (9)0.3096 (2)0.0595 (16)
H25A0.24790.07770.29530.089*
H25B0.1640−0.02430.31650.089*
H25C0.2326−0.13380.28270.089*
C260.3805 (4)−0.0846 (9)0.3637 (2)0.0552 (14)
H26A0.3996−0.00770.33430.083*
H26B0.4014−0.20910.35890.083*
H26C0.4055−0.03760.39920.083*
C270.2456 (5)−0.1394 (8)0.4071 (3)0.0586 (15)
C280.1422 (3)−0.1422 (8)0.4065 (3)0.0530 (13)
H28A0.1174−0.22150.37680.080*
H28B0.1191−0.01880.40050.080*
H28C0.1253−0.18800.44170.080*
N10.1455 (2)0.2367 (5)0.51787 (14)0.0328 (8)
N20.3234 (2)0.2223 (6)0.53358 (15)0.0347 (8)
N30.3510 (3)0.4285 (6)0.34392 (18)0.0497 (11)
N40.1615 (3)0.4498 (6)0.32826 (16)0.0465 (10)
N50.2799 (3)−0.0837 (7)0.36185 (19)0.0558 (12)
O10.3691 (3)0.3545 (6)0.67766 (17)0.0612 (11)
O20.3140 (2)0.0834 (6)0.64574 (14)0.0533 (10)
O1W0.2181 (3)−0.1484 (5)0.55112 (14)0.0475 (9)
HW110.241 (4)−0.181 (7)0.5213 (13)0.064 (19)*
HW120.234 (3)−0.239 (5)0.5731 (15)0.044 (15)*
O30.1262 (2)0.1001 (6)0.63021 (13)0.0490 (9)
O2W0.2320 (3)0.5306 (7)0.61437 (18)0.0654 (12)
HW210.186 (3)0.510 (12)0.632 (3)0.11 (3)*
HW220.276 (3)0.545 (7)0.640 (3)0.14 (4)*
O40.0964 (3)0.3738 (5)0.66852 (15)0.0518 (9)
O50.2951 (3)−0.1872 (6)0.45047 (14)0.0563 (10)
Cu10.22665 (4)0.15296 (9)0.58553 (2)0.03622 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (2)0.057 (3)0.039 (2)0.001 (2)−0.004 (2)0.000 (2)
C20.031 (2)0.066 (4)0.052 (3)−0.003 (2)0.003 (2)−0.001 (3)
C30.042 (3)0.046 (3)0.046 (3)−0.007 (2)0.016 (2)0.001 (2)
C40.038 (2)0.035 (2)0.034 (2)−0.005 (2)0.0055 (18)−0.0019 (19)
C50.033 (2)0.033 (2)0.029 (2)−0.0013 (18)0.0036 (17)−0.0034 (17)
C60.035 (2)0.026 (2)0.0284 (19)0.0021 (17)0.0013 (17)−0.0028 (16)
C70.034 (2)0.054 (3)0.040 (2)0.000 (2)0.006 (2)0.005 (2)
C80.027 (2)0.062 (3)0.053 (3)0.003 (2)0.000 (2)0.002 (3)
C90.041 (2)0.044 (3)0.039 (2)0.007 (2)−0.006 (2)−0.001 (2)
C100.041 (2)0.030 (2)0.031 (2)0.0021 (19)−0.0005 (18)−0.0013 (18)
C110.050 (3)0.032 (2)0.031 (2)−0.002 (2)0.010 (2)0.0023 (18)
C120.047 (3)0.029 (2)0.028 (2)0.0007 (19)0.0039 (18)0.0008 (17)
C130.082 (4)0.044 (3)0.029 (2)0.007 (3)0.002 (2)0.010 (2)
C140.090 (5)0.045 (3)0.039 (3)0.005 (3)0.023 (3)0.009 (2)
C150.038 (2)0.065 (4)0.0213 (19)0.000 (2)0.0000 (18)0.001 (2)
C160.032 (2)0.050 (3)0.026 (2)−0.002 (2)0.0028 (17)−0.0013 (19)
C170.035 (3)0.042 (4)0.026 (3)0.0000.005 (2)0.000
C180.041 (3)0.052 (3)0.042 (3)−0.008 (2)−0.007 (2)−0.006 (2)
C190.049 (4)0.053 (5)0.071 (5)0.000−0.004 (4)0.000
C200.031 (2)0.050 (3)0.0251 (19)0.002 (2)0.0021 (17)−0.0001 (19)
C210.030 (2)0.043 (2)0.0222 (18)−0.0035 (18)0.0014 (16)−0.0005 (17)
C220.033 (3)0.040 (3)0.023 (3)0.0000.002 (2)0.000
C230.047 (3)0.044 (3)0.032 (2)0.005 (2)0.008 (2)−0.008 (2)
C240.062 (5)0.030 (4)0.047 (4)0.0000.007 (3)0.000
C250.080 (4)0.052 (3)0.044 (3)0.000 (3)−0.014 (3)0.010 (3)
C260.044 (3)0.069 (4)0.055 (3)−0.003 (3)0.017 (2)−0.012 (3)
C270.073 (4)0.045 (3)0.061 (3)−0.003 (3)0.017 (3)−0.014 (3)
C280.037 (3)0.055 (3)0.068 (3)0.001 (2)0.010 (2)−0.009 (3)
N10.0294 (18)0.040 (2)0.0293 (17)0.0012 (16)0.0047 (14)−0.0005 (15)
N20.0292 (18)0.045 (2)0.0298 (17)−0.0003 (16)0.0007 (14)−0.0038 (16)
N30.059 (3)0.050 (3)0.042 (2)0.002 (2)0.016 (2)0.008 (2)
N40.060 (3)0.046 (2)0.033 (2)0.007 (2)0.0010 (19)0.0024 (18)
N50.060 (3)0.062 (3)0.046 (2)0.000 (2)0.004 (2)0.000 (2)
O10.065 (3)0.056 (3)0.059 (2)0.015 (2)−0.018 (2)−0.006 (2)
O20.052 (2)0.068 (3)0.0364 (17)−0.0087 (19)−0.0164 (16)0.0066 (17)
O1W0.060 (2)0.050 (2)0.0331 (17)0.0020 (18)0.0091 (16)0.0023 (16)
O30.050 (2)0.069 (2)0.0303 (16)−0.0023 (18)0.0203 (15)−0.0047 (16)
O2W0.061 (3)0.076 (3)0.060 (2)−0.001 (2)0.008 (2)0.033 (2)
O40.059 (2)0.047 (2)0.052 (2)−0.0009 (18)0.0232 (18)0.0075 (17)
O50.060 (2)0.075 (3)0.0345 (17)0.006 (2)0.0035 (16)0.0069 (18)
Cu10.0312 (3)0.0564 (4)0.0209 (2)0.0002 (3)0.00140 (19)−0.0004 (2)
Geometric parameters (Å, °) top
C1—N21.331 (6)C18—H180.9300
C1—C21.397 (7)C19—C18i1.387 (7)
C1—H10.9300C19—H190.9300
C2—C31.351 (7)C20—O41.234 (6)
C2—H20.9300C20—O31.274 (6)
C3—C41.408 (7)C20—C211.518 (6)
C3—H30.9300C21—C231.385 (7)
C4—C51.396 (6)C21—C221.405 (5)
C4—C111.453 (6)C22—C21ii1.405 (5)
C5—N21.363 (5)C22—H220.9300
C5—C61.437 (6)C23—C241.384 (6)
C6—N11.361 (5)C23—H230.9300
C6—C101.406 (6)C24—C23ii1.384 (6)
C7—N11.318 (6)C24—H240.9300
C7—C81.400 (7)C25—N51.462 (7)
C7—H70.9300C25—H25A0.9600
C8—C91.362 (7)C25—H25B0.9600
C8—H80.9300C25—H25C0.9600
C9—C101.399 (7)C26—N51.489 (7)
C9—H90.9300C26—H26A0.9600
C10—C121.473 (6)C26—H26B0.9600
C11—N31.363 (6)C26—H26C0.9600
C11—C121.388 (7)C27—O51.267 (7)
C12—N41.351 (6)C27—N51.302 (7)
C13—N41.311 (7)C27—C281.531 (8)
C13—C141.381 (9)C28—H28A0.9600
C13—H130.9300C28—H28B0.9600
C14—N31.318 (7)C28—H28C0.9600
C14—H140.9300Cu1—N12.026 (4)
C15—O11.221 (7)Cu1—N22.043 (4)
C15—O21.277 (6)Cu1—O21.920 (3)
C15—C161.525 (7)Cu1—O31.947 (3)
C16—C181.378 (7)Cu1—O1W2.324 (4)
C16—C171.392 (6)O1W—HW110.85 (4)
C17—C16i1.392 (6)O1W—HW120.86 (4)
C17—H170.9300O2W—HW210.85 (5)
C18—C191.387 (7)O2W—HW220.86 (6)
N2—C1—C2123.5 (5)C23—C21—C22119.2 (4)
N2—C1—H1118.3C23—C21—C20121.0 (4)
C2—C1—H1118.3C22—C21—C20119.8 (4)
C3—C2—C1119.0 (5)C21—C22—C21ii119.9 (6)
C3—C2—H2120.5C21—C22—H22120.1
C1—C2—H2120.5C21ii—C22—H22120.1
C2—C3—C4119.9 (4)C24—C23—C21121.2 (5)
C2—C3—H3120.0C24—C23—H23119.4
C4—C3—H3120.0C21—C23—H23119.4
C5—C4—C3117.3 (4)C23ii—C24—C23119.4 (6)
C5—C4—C11118.3 (4)C23ii—C24—H24120.3
C3—C4—C11124.3 (4)C23—C24—H24120.3
N2—C5—C4123.0 (4)N5—C25—H25A109.5
N2—C5—C6115.6 (4)N5—C25—H25B109.5
C4—C5—C6121.3 (4)H25A—C25—H25B109.5
N1—C6—C10122.2 (4)N5—C25—H25C109.5
N1—C6—C5116.5 (4)H25A—C25—H25C109.5
C10—C6—C5121.3 (4)H25B—C25—H25C109.5
N1—C7—C8123.0 (4)N5—C26—H26A109.5
N1—C7—H7118.5N5—C26—H26B109.5
C8—C7—H7118.5H26A—C26—H26B109.5
C9—C8—C7119.3 (4)N5—C26—H26C109.5
C9—C8—H8120.3H26A—C26—H26C109.5
C7—C8—H8120.3H26B—C26—H26C109.5
C8—C9—C10119.4 (4)O5—C27—N5121.8 (6)
C8—C9—H9120.3O5—C27—C28120.8 (5)
C10—C9—H9120.3N5—C27—C28117.3 (6)
C9—C10—C6117.9 (4)C27—C28—H28A109.5
C9—C10—C12124.9 (4)C27—C28—H28B109.5
C6—C10—C12117.1 (4)H28A—C28—H28B109.5
N3—C11—C12121.2 (4)C27—C28—H28C109.5
N3—C11—C4118.0 (4)H28A—C28—H28C109.5
C12—C11—C4120.8 (4)H28B—C28—H28C109.5
N4—C12—C11121.8 (4)C7—N1—C6118.3 (4)
N4—C12—C10117.0 (4)C7—N1—Cu1128.0 (3)
C11—C12—C10121.1 (4)C6—N1—Cu1113.7 (3)
N4—C13—C14121.8 (5)C1—N2—C5117.2 (4)
N4—C13—H13119.1C1—N2—Cu1129.2 (3)
C14—C13—H13119.1C5—N2—Cu1113.5 (3)
N3—C14—C13123.8 (5)C14—N3—C11115.0 (5)
N3—C14—H14118.1C13—N4—C12116.3 (5)
C13—C14—H14118.1C27—N5—C25124.3 (6)
O1—C15—O2126.3 (5)C27—N5—C26115.9 (5)
O1—C15—C16119.9 (4)C25—N5—C26119.6 (5)
O2—C15—C16113.8 (5)C15—O2—Cu1129.5 (4)
C18—C16—C17119.8 (5)Cu1—O1W—HW11123 (4)
C18—C16—C15121.2 (4)Cu1—O1W—HW12119 (3)
C17—C16—C15119.0 (5)HW11—O1W—HW12101 (3)
C16—C17—C16i120.2 (6)C20—O3—Cu1128.4 (3)
C16—C17—H17119.9HW21—O2W—HW22105 (3)
C16i—C17—H17119.9O2—Cu1—O391.92 (16)
C16—C18—C19119.9 (5)O2—Cu1—N1174.00 (16)
C16—C18—H18120.0O3—Cu1—N193.99 (15)
C19—C18—H18120.0O2—Cu1—N293.37 (16)
C18i—C19—C18120.4 (8)O3—Cu1—N2174.49 (15)
C18i—C19—H19119.8N1—Cu1—N280.69 (14)
C18—C19—H19119.8O2—Cu1—O1W92.00 (16)
O4—C20—O3126.3 (4)O3—Cu1—O1W89.51 (15)
O4—C20—C21119.6 (4)N1—Cu1—O1W89.09 (14)
O3—C20—C21114.1 (4)N2—Cu1—O1W91.83 (14)
N2—C1—C2—C3−2.4 (9)C22—C21—C23—C24−0.2 (6)
C1—C2—C3—C41.7 (8)C20—C21—C23—C24178.8 (3)
C2—C3—C4—C5−0.7 (7)C21—C23—C24—C23ii0.1 (3)
C2—C3—C4—C11−177.0 (5)C8—C7—N1—C60.3 (7)
C3—C4—C5—N20.2 (7)C8—C7—N1—Cu1−177.9 (4)
C11—C4—C5—N2176.7 (4)C10—C6—N1—C7−0.2 (6)
C3—C4—C5—C6−177.9 (4)C5—C6—N1—C7−177.8 (4)
C11—C4—C5—C6−1.4 (7)C10—C6—N1—Cu1178.2 (3)
N2—C5—C6—N1−1.0 (6)C5—C6—N1—Cu10.7 (5)
C4—C5—C6—N1177.2 (4)C2—C1—N2—C51.9 (8)
N2—C5—C6—C10−178.6 (4)C2—C1—N2—Cu1177.8 (4)
C4—C5—C6—C10−0.3 (7)C4—C5—N2—C1−0.8 (7)
N1—C7—C8—C9−0.1 (8)C6—C5—N2—C1177.4 (4)
C7—C8—C9—C10−0.1 (8)C4—C5—N2—Cu1−177.4 (3)
C8—C9—C10—C60.2 (7)C6—C5—N2—Cu10.8 (5)
C8—C9—C10—C12176.0 (5)C13—C14—N3—C112.7 (8)
N1—C6—C10—C90.0 (7)C12—C11—N3—C14−2.1 (7)
C5—C6—C10—C9177.4 (4)C4—C11—N3—C14177.5 (5)
N1—C6—C10—C12−176.2 (4)C14—C13—N4—C12−0.1 (8)
C5—C6—C10—C121.2 (6)C11—C12—N4—C130.6 (7)
C5—C4—C11—N3−177.4 (4)C10—C12—N4—C13−177.2 (4)
C3—C4—C11—N3−1.2 (7)O5—C27—N5—C25176.3 (5)
C5—C4—C11—C122.2 (7)C28—C27—N5—C25−4.6 (8)
C3—C4—C11—C12178.4 (5)O5—C27—N5—C261.5 (8)
N3—C11—C12—N40.5 (7)C28—C27—N5—C26−179.4 (5)
C4—C11—C12—N4−179.1 (4)O1—C15—O2—Cu16.5 (8)
N3—C11—C12—C10178.2 (4)C16—C15—O2—Cu1−172.2 (3)
C4—C11—C12—C10−1.3 (7)O4—C20—O3—Cu125.4 (7)
C9—C10—C12—N41.6 (7)C21—C20—O3—Cu1−156.0 (3)
C6—C10—C12—N4177.5 (4)C15—O2—Cu1—O3−107.8 (4)
C9—C10—C12—C11−176.2 (5)C15—O2—Cu1—N270.6 (4)
C6—C10—C12—C11−0.4 (6)C15—O2—Cu1—O1W162.6 (4)
N4—C13—C14—N3−1.8 (9)C20—O3—Cu1—O282.1 (4)
O1—C15—C16—C18179.8 (5)C20—O3—Cu1—N1−96.8 (4)
O2—C15—C16—C18−1.4 (6)C20—O3—Cu1—O1W174.1 (4)
O1—C15—C16—C17−0.7 (6)C7—N1—Cu1—O3−3.4 (4)
O2—C15—C16—C17178.0 (4)C6—N1—Cu1—O3178.4 (3)
C18—C16—C17—C16i0.3 (3)C7—N1—Cu1—N2178.1 (4)
C15—C16—C17—C16i−179.2 (4)C6—N1—Cu1—N2−0.2 (3)
C17—C16—C18—C19−0.5 (7)C7—N1—Cu1—O1W86.1 (4)
C15—C16—C18—C19178.9 (4)C6—N1—Cu1—O1W−92.2 (3)
C16—C18—C19—C18i0.3 (3)C1—N2—Cu1—O24.4 (5)
O4—C20—C21—C23−176.6 (5)C5—N2—Cu1—O2−179.4 (3)
O3—C20—C21—C234.6 (6)C1—N2—Cu1—N1−176.4 (5)
O4—C20—C21—C222.4 (6)C5—N2—Cu1—N1−0.3 (3)
O3—C20—C21—C22−176.4 (3)C1—N2—Cu1—O1W−87.7 (4)
C23—C21—C22—C21ii0.1 (3)C5—N2—Cu1—O1W88.4 (3)
C20—C21—C22—C21ii−178.9 (4)
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x, y, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—HW12···O2Wiii0.86 (4)1.93 (2)2.765 (6)162 (5)
O1W—HW11···O50.85 (4)1.94 (2)2.772 (5)165 (5)
O2W—HW22···O10.86 (6)2.10 (4)2.740 (6)131 (4)
O2W—HW21···O40.85 (4)1.92 (4)2.732 (6)159 (9)
Symmetry codes: (iii) x, y−1, z.
Table 1
Selected geometric parameters (Å) top
Cu1—N12.026 (4)Cu1—O31.947 (3)
Cu1—N22.043 (4)Cu1—O1W2.324 (4)
Cu1—O21.920 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—HW12···O2Wi0.86 (4)1.93 (2)2.765 (6)162 (5)
O1W—HW11···O50.85 (4)1.94 (2)2.772 (5)165 (5)
O2W—HW22···O10.86 (6)2.10 (4)2.740 (6)131 (4)
O2W—HW21···O40.85 (4)1.92 (4)2.732 (6)159 (9)
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

The author thanks Qiqihar University for supporting this work.

references
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