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

Zhang, W.-Z.

doi:10.1107/S1600536807023082

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

W.-Z. Zhang

In the title compound, [Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]·C₄H₉NO·H₂O, the Cu^II 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 Cu^II 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023082/hb2408sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023082/hb2408Isup2.hkl Contains datablock I

CCDC reference: 650689

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.068
wR factor = 0.184
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.52
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.11
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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 Cu^II 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 Cu^II 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 Cu^II atom is five-coordinated and exhibits a distorted square-pyramidal coordination environment. The Cu^II 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).

Structure description top

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

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

	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.
	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·H₂O	F(000) = 1204
M_r = 583.05	D_x = 1.516 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 17473 reflections
a = 14.829 (3) Å	θ = 3.2–27.5°
b = 7.2111 (14) Å	µ = 0.91 mm⁻¹
c = 23.976 (5) Å	T = 293 K
β = 95.00 (3)°	Block, blue
V = 2554.1 (9) Å³	0.33 × 0.31 × 0.30 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5813 independent reflections
Radiation source: rotating anode	4102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −19→18
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
T_min = 0.733, T_max = 0.766	l = −31→31
23862 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0676P)² + 7.6293P] where P = (F_o² + 2F_c²)/3
5813 reflections	(Δ/σ)_max < 0.001
373 parameters	Δρ_max = 1.09 e Å⁻³
7 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]·C₄H₉NO·H₂O	V = 2554.1 (9) Å³
M_r = 583.05	Z = 4
Monoclinic, P2/c	Mo Kα radiation
a = 14.829 (3) Å	µ = 0.91 mm⁻¹
b = 7.2111 (14) Å	T = 293 K
c = 23.976 (5) Å	0.33 × 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)
T_min = 0.733, T_max = 0.766	R_int = 0.061
23862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	7 restraints
wR(F²) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.09 e Å⁻³
5813 reflections	Δρ_min = −0.43 e Å⁻³
373 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
C1	0.4129 (3)	0.2052 (8)	0.5417 (2)	0.0440 (12)
H1	0.4376	0.1590	0.5759	0.053*
C2	0.4719 (3)	0.2530 (8)	0.5017 (2)	0.0497 (13)
H2	0.5342	0.2429	0.5097	0.060*
C3	0.4370 (3)	0.3140 (7)	0.4510 (2)	0.0440 (11)
H3	0.4752	0.3432	0.4235	0.053*
C4	0.3426 (3)	0.3333 (6)	0.43985 (18)	0.0357 (10)
C5	0.2887 (3)	0.2852 (6)	0.48253 (17)	0.0314 (9)
C6	0.1916 (3)	0.2943 (6)	0.47436 (17)	0.0297 (9)
C7	0.0563 (3)	0.2370 (7)	0.5113 (2)	0.0424 (11)
H7	0.0246	0.1983	0.5411	0.051*
C8	0.0072 (3)	0.2930 (8)	0.4617 (2)	0.0475 (12)
H8	−0.0558	0.2909	0.4587	0.057*
C9	0.0525 (3)	0.3505 (7)	0.4178 (2)	0.0422 (11)
H9	0.0208	0.3879	0.3845	0.051*
C10	0.1472 (3)	0.3528 (6)	0.42319 (18)	0.0339 (9)
C11	0.2981 (3)	0.3891 (6)	0.38611 (18)	0.0376 (10)
C12	0.2044 (3)	0.4006 (6)	0.37806 (17)	0.0346 (10)
C13	0.2132 (4)	0.4844 (7)	0.2878 (2)	0.0522 (14)
H13	0.1863	0.5186	0.2528	0.063*
C14	0.3063 (5)	0.4713 (8)	0.2957 (2)	0.0570 (15)
H14	0.3395	0.4941	0.2652	0.068*
C15	0.3677 (3)	0.1853 (8)	0.67698 (17)	0.0414 (12)
C16	0.4361 (3)	0.0762 (7)	0.71521 (17)	0.0361 (10)
C17	0.5000	0.1725 (9)	0.7500	0.0340 (13)
H17	0.5000	0.3015	0.7500	0.041*
C18	0.4360 (3)	−0.1149 (8)	0.7155 (2)	0.0456 (12)
H18	0.3931	−0.1798	0.6925	0.055*
C19	0.5000	−0.2104 (12)	0.7500	0.058 (2)
H19	0.5000	−0.3394	0.7500	0.070*
C20	0.0931 (3)	0.2029 (7)	0.66650 (17)	0.0352 (10)
C21	0.0441 (3)	0.0973 (6)	0.70954 (16)	0.0319 (9)
C22	0.0000	0.1949 (9)	0.7500	0.0318 (13)
H22	0.0000	0.3239	0.7500	0.038*
C23	0.0432 (3)	−0.0947 (7)	0.71019 (19)	0.0407 (11)
H23	0.0721	−0.1597	0.6834	0.049*
C24	0.0000	−0.1916 (10)	0.7500	0.0461 (17)
H24	0.0000	−0.3206	0.7500	0.055*
C25	0.2265 (4)	−0.0370 (9)	0.3096 (2)	0.0595 (16)
H25A	0.2479	0.0777	0.2953	0.089*
H25B	0.1640	−0.0243	0.3165	0.089*
H25C	0.2326	−0.1338	0.2827	0.089*
C26	0.3805 (4)	−0.0846 (9)	0.3637 (2)	0.0552 (14)
H26A	0.3996	−0.0077	0.3343	0.083*
H26B	0.4014	−0.2091	0.3589	0.083*
H26C	0.4055	−0.0376	0.3992	0.083*
C27	0.2456 (5)	−0.1394 (8)	0.4071 (3)	0.0586 (15)
C28	0.1422 (3)	−0.1422 (8)	0.4065 (3)	0.0530 (13)
H28A	0.1174	−0.2215	0.3768	0.080*
H28B	0.1191	−0.0188	0.4005	0.080*
H28C	0.1253	−0.1880	0.4417	0.080*
N1	0.1455 (2)	0.2367 (5)	0.51787 (14)	0.0328 (8)
N2	0.3234 (2)	0.2223 (6)	0.53358 (15)	0.0347 (8)
N3	0.3510 (3)	0.4285 (6)	0.34392 (18)	0.0497 (11)
N4	0.1615 (3)	0.4498 (6)	0.32826 (16)	0.0465 (10)
N5	0.2799 (3)	−0.0837 (7)	0.36185 (19)	0.0558 (12)
O1	0.3691 (3)	0.3545 (6)	0.67766 (17)	0.0612 (11)
O2	0.3140 (2)	0.0834 (6)	0.64574 (14)	0.0533 (10)
O1W	0.2181 (3)	−0.1484 (5)	0.55112 (14)	0.0475 (9)
HW11	0.241 (4)	−0.181 (7)	0.5213 (13)	0.064 (19)*
HW12	0.234 (3)	−0.239 (5)	0.5731 (15)	0.044 (15)*
O3	0.1262 (2)	0.1001 (6)	0.63021 (13)	0.0490 (9)
O2W	0.2320 (3)	0.5306 (7)	0.61437 (18)	0.0654 (12)
HW21	0.186 (3)	0.510 (12)	0.632 (3)	0.11 (3)*
HW22	0.276 (3)	0.545 (7)	0.640 (3)	0.14 (4)*
O4	0.0964 (3)	0.3738 (5)	0.66852 (15)	0.0518 (9)
O5	0.2951 (3)	−0.1872 (6)	0.45047 (14)	0.0563 (10)
Cu1	0.22665 (4)	0.15296 (9)	0.58553 (2)	0.03622 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.035 (2)	0.057 (3)	0.039 (2)	0.001 (2)	−0.004 (2)	0.000 (2)
C2	0.031 (2)	0.066 (4)	0.052 (3)	−0.003 (2)	0.003 (2)	−0.001 (3)
C3	0.042 (3)	0.046 (3)	0.046 (3)	−0.007 (2)	0.016 (2)	0.001 (2)
C4	0.038 (2)	0.035 (2)	0.034 (2)	−0.005 (2)	0.0055 (18)	−0.0019 (19)
C5	0.033 (2)	0.033 (2)	0.029 (2)	−0.0013 (18)	0.0036 (17)	−0.0034 (17)
C6	0.035 (2)	0.026 (2)	0.0284 (19)	0.0021 (17)	0.0013 (17)	−0.0028 (16)
C7	0.034 (2)	0.054 (3)	0.040 (2)	0.000 (2)	0.006 (2)	0.005 (2)
C8	0.027 (2)	0.062 (3)	0.053 (3)	0.003 (2)	0.000 (2)	0.002 (3)
C9	0.041 (2)	0.044 (3)	0.039 (2)	0.007 (2)	−0.006 (2)	−0.001 (2)
C10	0.041 (2)	0.030 (2)	0.031 (2)	0.0021 (19)	−0.0005 (18)	−0.0013 (18)
C11	0.050 (3)	0.032 (2)	0.031 (2)	−0.002 (2)	0.010 (2)	0.0023 (18)
C12	0.047 (3)	0.029 (2)	0.028 (2)	0.0007 (19)	0.0039 (18)	0.0008 (17)
C13	0.082 (4)	0.044 (3)	0.029 (2)	0.007 (3)	0.002 (2)	0.010 (2)
C14	0.090 (5)	0.045 (3)	0.039 (3)	0.005 (3)	0.023 (3)	0.009 (2)
C15	0.038 (2)	0.065 (4)	0.0213 (19)	0.000 (2)	0.0000 (18)	0.001 (2)
C16	0.032 (2)	0.050 (3)	0.026 (2)	−0.002 (2)	0.0028 (17)	−0.0013 (19)
C17	0.035 (3)	0.042 (4)	0.026 (3)	0.000	0.005 (2)	0.000
C18	0.041 (3)	0.052 (3)	0.042 (3)	−0.008 (2)	−0.007 (2)	−0.006 (2)
C19	0.049 (4)	0.053 (5)	0.071 (5)	0.000	−0.004 (4)	0.000
C20	0.031 (2)	0.050 (3)	0.0251 (19)	0.002 (2)	0.0021 (17)	−0.0001 (19)
C21	0.030 (2)	0.043 (2)	0.0222 (18)	−0.0035 (18)	0.0014 (16)	−0.0005 (17)
C22	0.033 (3)	0.040 (3)	0.023 (3)	0.000	0.002 (2)	0.000
C23	0.047 (3)	0.044 (3)	0.032 (2)	0.005 (2)	0.008 (2)	−0.008 (2)
C24	0.062 (5)	0.030 (4)	0.047 (4)	0.000	0.007 (3)	0.000
C25	0.080 (4)	0.052 (3)	0.044 (3)	0.000 (3)	−0.014 (3)	0.010 (3)
C26	0.044 (3)	0.069 (4)	0.055 (3)	−0.003 (3)	0.017 (2)	−0.012 (3)
C27	0.073 (4)	0.045 (3)	0.061 (3)	−0.003 (3)	0.017 (3)	−0.014 (3)
C28	0.037 (3)	0.055 (3)	0.068 (3)	0.001 (2)	0.010 (2)	−0.009 (3)
N1	0.0294 (18)	0.040 (2)	0.0293 (17)	0.0012 (16)	0.0047 (14)	−0.0005 (15)
N2	0.0292 (18)	0.045 (2)	0.0298 (17)	−0.0003 (16)	0.0007 (14)	−0.0038 (16)
N3	0.059 (3)	0.050 (3)	0.042 (2)	0.002 (2)	0.016 (2)	0.008 (2)
N4	0.060 (3)	0.046 (2)	0.033 (2)	0.007 (2)	0.0010 (19)	0.0024 (18)
N5	0.060 (3)	0.062 (3)	0.046 (2)	0.000 (2)	0.004 (2)	0.000 (2)
O1	0.065 (3)	0.056 (3)	0.059 (2)	0.015 (2)	−0.018 (2)	−0.006 (2)
O2	0.052 (2)	0.068 (3)	0.0364 (17)	−0.0087 (19)	−0.0164 (16)	0.0066 (17)
O1W	0.060 (2)	0.050 (2)	0.0331 (17)	0.0020 (18)	0.0091 (16)	0.0023 (16)
O3	0.050 (2)	0.069 (2)	0.0303 (16)	−0.0023 (18)	0.0203 (15)	−0.0047 (16)
O2W	0.061 (3)	0.076 (3)	0.060 (2)	−0.001 (2)	0.008 (2)	0.033 (2)
O4	0.059 (2)	0.047 (2)	0.052 (2)	−0.0009 (18)	0.0232 (18)	0.0075 (17)
O5	0.060 (2)	0.075 (3)	0.0345 (17)	0.006 (2)	0.0035 (16)	0.0069 (18)
Cu1	0.0312 (3)	0.0564 (4)	0.0209 (2)	0.0002 (3)	0.00140 (19)	−0.0004 (2)

Geometric parameters (Å, º) top

C1—N2	1.331 (6)	C18—H18	0.9300
C1—C2	1.397 (7)	C19—C18ⁱ	1.387 (7)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.351 (7)	C20—O4	1.234 (6)
C2—H2	0.9300	C20—O3	1.274 (6)
C3—C4	1.408 (7)	C20—C21	1.518 (6)
C3—H3	0.9300	C21—C23	1.385 (7)
C4—C5	1.396 (6)	C21—C22	1.405 (5)
C4—C11	1.453 (6)	C22—C21ⁱⁱ	1.405 (5)
C5—N2	1.363 (5)	C22—H22	0.9300
C5—C6	1.437 (6)	C23—C24	1.384 (6)
C6—N1	1.361 (5)	C23—H23	0.9300
C6—C10	1.406 (6)	C24—C23ⁱⁱ	1.384 (6)
C7—N1	1.318 (6)	C24—H24	0.9300
C7—C8	1.400 (7)	C25—N5	1.462 (7)
C7—H7	0.9300	C25—H25A	0.9600
C8—C9	1.362 (7)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C10	1.399 (7)	C26—N5	1.489 (7)
C9—H9	0.9300	C26—H26A	0.9600
C10—C12	1.473 (6)	C26—H26B	0.9600
C11—N3	1.363 (6)	C26—H26C	0.9600
C11—C12	1.388 (7)	C27—O5	1.267 (7)
C12—N4	1.351 (6)	C27—N5	1.302 (7)
C13—N4	1.311 (7)	C27—C28	1.531 (8)
C13—C14	1.381 (9)	C28—H28A	0.9600
C13—H13	0.9300	C28—H28B	0.9600
C14—N3	1.318 (7)	C28—H28C	0.9600
C14—H14	0.9300	Cu1—N1	2.026 (4)
C15—O1	1.221 (7)	Cu1—N2	2.043 (4)
C15—O2	1.277 (6)	Cu1—O2	1.920 (3)
C15—C16	1.525 (7)	Cu1—O3	1.947 (3)
C16—C18	1.378 (7)	Cu1—O1W	2.324 (4)
C16—C17	1.392 (6)	O1W—HW11	0.85 (4)
C17—C16ⁱ	1.392 (6)	O1W—HW12	0.86 (4)
C17—H17	0.9300	O2W—HW21	0.85 (5)
C18—C19	1.387 (7)	O2W—HW22	0.86 (6)

N2—C1—C2	123.5 (5)	C23—C21—C22	119.2 (4)
N2—C1—H1	118.3	C23—C21—C20	121.0 (4)
C2—C1—H1	118.3	C22—C21—C20	119.8 (4)
C3—C2—C1	119.0 (5)	C21—C22—C21ⁱⁱ	119.9 (6)
C3—C2—H2	120.5	C21—C22—H22	120.1
C1—C2—H2	120.5	C21ⁱⁱ—C22—H22	120.1
C2—C3—C4	119.9 (4)	C24—C23—C21	121.2 (5)
C2—C3—H3	120.0	C24—C23—H23	119.4
C4—C3—H3	120.0	C21—C23—H23	119.4
C5—C4—C3	117.3 (4)	C23ⁱⁱ—C24—C23	119.4 (6)
C5—C4—C11	118.3 (4)	C23ⁱⁱ—C24—H24	120.3
C3—C4—C11	124.3 (4)	C23—C24—H24	120.3
N2—C5—C4	123.0 (4)	N5—C25—H25A	109.5
N2—C5—C6	115.6 (4)	N5—C25—H25B	109.5
C4—C5—C6	121.3 (4)	H25A—C25—H25B	109.5
N1—C6—C10	122.2 (4)	N5—C25—H25C	109.5
N1—C6—C5	116.5 (4)	H25A—C25—H25C	109.5
C10—C6—C5	121.3 (4)	H25B—C25—H25C	109.5
N1—C7—C8	123.0 (4)	N5—C26—H26A	109.5
N1—C7—H7	118.5	N5—C26—H26B	109.5
C8—C7—H7	118.5	H26A—C26—H26B	109.5
C9—C8—C7	119.3 (4)	N5—C26—H26C	109.5
C9—C8—H8	120.3	H26A—C26—H26C	109.5
C7—C8—H8	120.3	H26B—C26—H26C	109.5
C8—C9—C10	119.4 (4)	O5—C27—N5	121.8 (6)
C8—C9—H9	120.3	O5—C27—C28	120.8 (5)
C10—C9—H9	120.3	N5—C27—C28	117.3 (6)
C9—C10—C6	117.9 (4)	C27—C28—H28A	109.5
C9—C10—C12	124.9 (4)	C27—C28—H28B	109.5
C6—C10—C12	117.1 (4)	H28A—C28—H28B	109.5
N3—C11—C12	121.2 (4)	C27—C28—H28C	109.5
N3—C11—C4	118.0 (4)	H28A—C28—H28C	109.5
C12—C11—C4	120.8 (4)	H28B—C28—H28C	109.5
N4—C12—C11	121.8 (4)	C7—N1—C6	118.3 (4)
N4—C12—C10	117.0 (4)	C7—N1—Cu1	128.0 (3)
C11—C12—C10	121.1 (4)	C6—N1—Cu1	113.7 (3)
N4—C13—C14	121.8 (5)	C1—N2—C5	117.2 (4)
N4—C13—H13	119.1	C1—N2—Cu1	129.2 (3)
C14—C13—H13	119.1	C5—N2—Cu1	113.5 (3)
N3—C14—C13	123.8 (5)	C14—N3—C11	115.0 (5)
N3—C14—H14	118.1	C13—N4—C12	116.3 (5)
C13—C14—H14	118.1	C27—N5—C25	124.3 (6)
O1—C15—O2	126.3 (5)	C27—N5—C26	115.9 (5)
O1—C15—C16	119.9 (4)	C25—N5—C26	119.6 (5)
O2—C15—C16	113.8 (5)	C15—O2—Cu1	129.5 (4)
C18—C16—C17	119.8 (5)	Cu1—O1W—HW11	123 (4)
C18—C16—C15	121.2 (4)	Cu1—O1W—HW12	119 (3)
C17—C16—C15	119.0 (5)	HW11—O1W—HW12	101 (3)
C16—C17—C16ⁱ	120.2 (6)	C20—O3—Cu1	128.4 (3)
C16—C17—H17	119.9	HW21—O2W—HW22	105 (3)
C16ⁱ—C17—H17	119.9	O2—Cu1—O3	91.92 (16)
C16—C18—C19	119.9 (5)	O2—Cu1—N1	174.00 (16)
C16—C18—H18	120.0	O3—Cu1—N1	93.99 (15)
C19—C18—H18	120.0	O2—Cu1—N2	93.37 (16)
C18ⁱ—C19—C18	120.4 (8)	O3—Cu1—N2	174.49 (15)
C18ⁱ—C19—H19	119.8	N1—Cu1—N2	80.69 (14)
C18—C19—H19	119.8	O2—Cu1—O1W	92.00 (16)
O4—C20—O3	126.3 (4)	O3—Cu1—O1W	89.51 (15)
O4—C20—C21	119.6 (4)	N1—Cu1—O1W	89.09 (14)
O3—C20—C21	114.1 (4)	N2—Cu1—O1W	91.83 (14)

N2—C1—C2—C3	−2.4 (9)	C22—C21—C23—C24	−0.2 (6)
C1—C2—C3—C4	1.7 (8)	C20—C21—C23—C24	178.8 (3)
C2—C3—C4—C5	−0.7 (7)	C21—C23—C24—C23ⁱⁱ	0.1 (3)
C2—C3—C4—C11	−177.0 (5)	C8—C7—N1—C6	0.3 (7)
C3—C4—C5—N2	0.2 (7)	C8—C7—N1—Cu1	−177.9 (4)
C11—C4—C5—N2	176.7 (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—Cu1	178.2 (3)
N2—C5—C6—N1	−1.0 (6)	C5—C6—N1—Cu1	0.7 (5)
C4—C5—C6—N1	177.2 (4)	C2—C1—N2—C5	1.9 (8)
N2—C5—C6—C10	−178.6 (4)	C2—C1—N2—Cu1	177.8 (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—C1	177.4 (4)
C7—C8—C9—C10	−0.1 (8)	C4—C5—N2—Cu1	−177.4 (3)
C8—C9—C10—C6	0.2 (7)	C6—C5—N2—Cu1	0.8 (5)
C8—C9—C10—C12	176.0 (5)	C13—C14—N3—C11	2.7 (8)
N1—C6—C10—C9	0.0 (7)	C12—C11—N3—C14	−2.1 (7)
C5—C6—C10—C9	177.4 (4)	C4—C11—N3—C14	177.5 (5)
N1—C6—C10—C12	−176.2 (4)	C14—C13—N4—C12	−0.1 (8)
C5—C6—C10—C12	1.2 (6)	C11—C12—N4—C13	0.6 (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—C25	176.3 (5)
C5—C4—C11—C12	2.2 (7)	C28—C27—N5—C25	−4.6 (8)
C3—C4—C11—C12	178.4 (5)	O5—C27—N5—C26	1.5 (8)
N3—C11—C12—N4	0.5 (7)	C28—C27—N5—C26	−179.4 (5)
C4—C11—C12—N4	−179.1 (4)	O1—C15—O2—Cu1	6.5 (8)
N3—C11—C12—C10	178.2 (4)	C16—C15—O2—Cu1	−172.2 (3)
C4—C11—C12—C10	−1.3 (7)	O4—C20—O3—Cu1	25.4 (7)
C9—C10—C12—N4	1.6 (7)	C21—C20—O3—Cu1	−156.0 (3)
C6—C10—C12—N4	177.5 (4)	C15—O2—Cu1—O3	−107.8 (4)
C9—C10—C12—C11	−176.2 (5)	C15—O2—Cu1—N2	70.6 (4)
C6—C10—C12—C11	−0.4 (6)	C15—O2—Cu1—O1W	162.6 (4)
N4—C13—C14—N3	−1.8 (9)	C20—O3—Cu1—O2	82.1 (4)
O1—C15—C16—C18	179.8 (5)	C20—O3—Cu1—N1	−96.8 (4)
O2—C15—C16—C18	−1.4 (6)	C20—O3—Cu1—O1W	174.1 (4)
O1—C15—C16—C17	−0.7 (6)	C7—N1—Cu1—O3	−3.4 (4)
O2—C15—C16—C17	178.0 (4)	C6—N1—Cu1—O3	178.4 (3)
C18—C16—C17—C16ⁱ	0.3 (3)	C7—N1—Cu1—N2	178.1 (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—O1W	86.1 (4)
C15—C16—C18—C19	178.9 (4)	C6—N1—Cu1—O1W	−92.2 (3)
C16—C18—C19—C18ⁱ	0.3 (3)	C1—N2—Cu1—O2	4.4 (5)
O4—C20—C21—C23	−176.6 (5)	C5—N2—Cu1—O2	−179.4 (3)
O3—C20—C21—C23	4.6 (6)	C1—N2—Cu1—N1	−176.4 (5)
O4—C20—C21—C22	2.4 (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—C21ⁱⁱ	0.1 (3)	C5—N2—Cu1—O1W	88.4 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O2Wⁱⁱⁱ	0.86 (4)	1.93 (2)	2.765 (6)	162 (5)
O1W—HW11···O5	0.85 (4)	1.94 (2)	2.772 (5)	165 (5)
O2W—HW22···O1	0.86 (6)	2.10 (4)	2.740 (6)	131 (4)
O2W—HW21···O4	0.85 (4)	1.92 (4)	2.732 (6)	159 (9)

Symmetry code: (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]·C₄H₉NO·H₂O
M_r	583.05
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	293
a, b, c (Å)	14.829 (3), 7.2111 (14), 23.976 (5)
β (°)	95.00 (3)
V (Å³)	2554.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.33 × 0.31 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.733, 0.766
No. of measured, independent and observed [I > 2σ(I)] reflections	23862, 5813, 4102
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.184, 1.07
No. of reflections	5813
No. of parameters	373
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.43

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Selected bond lengths (Å) top

Cu1—N1	2.026 (4)	Cu1—O3	1.947 (3)
Cu1—N2	2.043 (4)	Cu1—O1W	2.324 (4)
Cu1—O2	1.920 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O2Wⁱ	0.86 (4)	1.93 (2)	2.765 (6)	162 (5)
O1W—HW11···O5	0.85 (4)	1.94 (2)	2.772 (5)	165 (5)
O2W—HW22···O1	0.86 (6)	2.10 (4)	2.740 (6)	131 (4)
O2W—HW21···O4	0.85 (4)	1.92 (4)	2.732 (6)	159 (9)

Symmetry code: (i) x, y−1, z.

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