Aqua­(3-carboxybenzoato-κO1)(nitrato-κO)(dipyrido[3,2-a:2′,3′-c]phenazine-κ2N4,N5)copper(II)

An, Y.; Li, X.-F.; Dong, L.-H.; Yin, Y.-S.

doi:10.1107/S1600536808029449

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1291-m1292

doi:10.1107/S1600536808029449

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Aqua(3-carboxybenzoato-κO¹)(nitrato-κO)(dipyrido[3,2-a:2′,3′-c]phenazine-κ²N⁴,N⁵)copper(II)

Yan An,^a Xiao-Feng Li,^a ^* Li-Hua Dong ^a and Yan-Sheng Yin ^a

^aInstitute of Marine Materials Science and Engineering, Shanghai Maritime University, Shanghai 200135, People's Republic of China
^*Correspondence e-mail: lxf_shmtu@yahoo.com.cn

(Received 22 August 2008; accepted 14 September 2008; online 20 September 2008)

The title complex, [Cu(C₈H₅O₄)(NO₃)(C₁₈H₁₀N₄)(H₂O)], was synthesized by reacting Cu(NO₃)₂, isophthalic acid and dipyridophenazine under hydrothermal conditions. The Cu^II ion is in a slightly distorted square-pyramidal coordination environment. In the crystal structure, intermolecular O—H⋯O hydrogen bonds connect complex molecules into chains along [001].

Related literature

For related literature, see: Gupta et al. (1992 ); Han & Ma (2006 ); Han et al. (2007 ); Hartshorn & Barton (1992 ); He & Han (2006 ); Murphy et al. (1993 ).

Experimental

Crystal data

[Cu(C₈H₅O₄)(NO₃)(C₁₈H₁₀N₄)(H₂O)]
M_r = 590.99
Triclinic, $[P \overline 1]$
a = 7.8965 (17) Å
b = 11.295 (4) Å
c = 14.533 (6) Å
α = 112.73 (3)°
β = 90.94 (3)°
γ = 102.60 (2)°
V = 1159.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 293 (2) K
0.37 × 0.32 × 0.24 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.707, T_max = 0.797
6320 measured reflections
5180 independent reflections
3353 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.198
S = 1.01
5180 reflections
367 parameters
39 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O1W	1.952 (3)
Cu1—O3	1.960 (3)
Cu1—N1	2.000 (4)
Cu1—N2	2.001 (4)
Cu1—O7	2.284 (4)

O1W—Cu1—O3	94.58 (14)
O1W—Cu1—N1	171.25 (17)
O3—Cu1—N1	89.65 (14)
O1W—Cu1—N2	92.03 (15)
O3—Cu1—N2	164.17 (16)
N1—Cu1—N2	82.02 (15)
O1W—Cu1—O7	97.54 (17)
O3—Cu1—O7	89.57 (16)
N1—Cu1—O7	90.14 (16)
N2—Cu1—O7	103.82 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O6ⁱ	0.841 (19)	2.08 (3)	2.856 (7)	153 (5)
O1W—H1WA⋯O5ⁱ	0.841 (19)	2.41 (3)	3.165 (6)	151 (6)
O1W—H1WB⋯O4	0.842 (19)	1.88 (4)	2.565 (5)	138 (6)
O2—H2B⋯O4ⁱⁱ	0.82	1.94	2.722 (4)	159
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+2, -z+2.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029449/lh2688sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029449/lh2688Isup2.hkl

checkCIF report

Comment top

Dipyridophenazine derivatives can be used as molecular light switches (Hartshorn & Barton, 1992) for the study of fast electron transfer through DNA (Murphy et al., 1993). A dipyridophenazine ruthenium(II) complex has been found to be a good cleavage agent with high affinity for DNA (Gupta et al., 1992). Recently, some examples of dinuclear copper(II) complexes of dipyridophenazine or isophthalate have been reported (He & Han, 2006; Han & Ma, 2006; Han et al., 2007). The synthesis and crystal structure of a mononuclear copper(II) complex with a dipyridophenazine and a hydrogenisophthalato ligand is presented herein.

The title complex (I) (Fig. 1) is formed by one dipyridophenazine ligand, one NO₃ ligand, one aqua ligand and one hydrogenisophthalato ligand coordinated to a Cu^II atom by three oxygen atoms and two nitrogen atoms in a slightly distorted square-pyramidal geometry. In the crystal structure, the mononuclear complex molecules are linked via intermolecular O—H···O hydrogen bonds (Table 2) forming one-dimensional chains along [001].

Related literature top

For related literature, see: Gupta et al. (1992); Han & Ma (2006); Han et al. (2007); Hartshorn & Barton (1992); He & Han (2006); Murphy et al. (1993).

Experimental top

A mixture of Cu(NO₃)₂.2H₂O (0.5 mmol, 0.120 g), isophthalic acid (0.5 mmol, 0.084 g), dipyridophenazine (0.5 mmol, 0.141 g) and water (10 ml) was mixed in a 23 ml Teflon reactor, which was heated at 453 K for six days and then cooled to room temperature at a rate of 5 K h^-1. Yield: 58%. CH&N analysis for C₂₆H₁₇N₅O₈Cu (found/calc): C, 53.05 (52.84), H, 2.94 (2.90), N, 11.96% (11.85%).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Aqua(3-carboxybenzoato-κO¹)(dipyrido[3,2-a:2',3'-c]phenazine- κ²N⁴,N⁵)(nitrato-κO)copper(II) top

Crystal data top

[Cu(C₈H₅O₄)(NO₃)(C₁₈H₁₀N₄)(H₂O)]	Z = 2
M_r = 590.99	F(000) = 602
Triclinic, P1	D_x = 1.693 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8965 (17) Å	Cell parameters from 2056 reflections
b = 11.295 (4) Å	θ = 3.0–23.0°
c = 14.533 (6) Å	µ = 1.01 mm⁻¹
α = 112.73 (3)°	T = 293 K
β = 90.94 (3)°	Block, green
γ = 102.60 (2)°	0.37 × 0.32 × 0.24 mm
V = 1159.4 (6) Å³

Data collection top

Bruker APEX area-detector diffractometer	5180 independent reflections
Radiation source: fine-focus sealed tube	3353 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −1→10
T_min = 0.707, T_max = 0.797	k = −13→13
6320 measured reflections	l = −18→18

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.1211P)²] where P = (F_o² + 2F_c²)/3
5180 reflections	(Δ/σ)_max < 0.001
367 parameters	Δρ_max = 0.60 e Å⁻³
39 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

[Cu(C₈H₅O₄)(NO₃)(C₁₈H₁₀N₄)(H₂O)]	γ = 102.60 (2)°
M_r = 590.99	V = 1159.4 (6) Å³
Triclinic, P1	Z = 2
a = 7.8965 (17) Å	Mo Kα radiation
b = 11.295 (4) Å	µ = 1.01 mm⁻¹
c = 14.533 (6) Å	T = 293 K
α = 112.73 (3)°	0.37 × 0.32 × 0.24 mm
β = 90.94 (3)°

Data collection top

Bruker APEX area-detector diffractometer	5180 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3353 reflections with I > 2σ(I)
T_min = 0.707, T_max = 0.797	R_int = 0.036
6320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	39 restraints
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.60 e Å⁻³
5180 reflections	Δρ_min = −0.92 e Å⁻³
367 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
Cu1	−0.27167 (8)	0.70493 (5)	0.50884 (4)	0.0396 (2)
C1	−0.2797 (7)	0.4150 (4)	0.4401 (3)	0.0445 (11)
H1A	−0.2211	0.4354	0.5023	0.053*
C2	−0.3193 (7)	0.2855 (5)	0.3703 (4)	0.0497 (13)
H2A	−0.2915	0.2195	0.3865	0.060*
C3	−0.4002 (7)	0.2552 (5)	0.2769 (4)	0.0428 (11)
H3A	−0.4269	0.1684	0.2293	0.051*
C4	−0.4426 (6)	0.3552 (4)	0.2532 (3)	0.0345 (9)
C5	−0.5234 (6)	0.3340 (4)	0.1558 (3)	0.0342 (9)
C6	−0.6258 (6)	0.1988 (4)	−0.0066 (3)	0.0373 (10)
C7	−0.6553 (7)	0.0742 (4)	−0.0887 (3)	0.0432 (11)
H7A	−0.6148	0.0059	−0.0826	0.052*
C8	−0.7424 (7)	0.0553 (5)	−0.1756 (4)	0.0495 (12)
H8A	−0.7629	−0.0272	−0.2287	0.059*
C9	−0.8031 (7)	0.1561 (5)	−0.1884 (3)	0.0484 (12)
H9A	−0.8635	0.1398	−0.2492	0.058*
C10	−0.7739 (7)	0.2774 (5)	−0.1122 (4)	0.0485 (12)
H10A	−0.8133	0.3445	−0.1211	0.058*
C11	−0.6829 (6)	0.3022 (4)	−0.0187 (3)	0.0385 (10)
C12	−0.5768 (6)	0.4395 (4)	0.1423 (3)	0.0345 (9)
C13	−0.5442 (6)	0.5688 (4)	0.2256 (3)	0.0370 (10)
C14	−0.6011 (7)	0.6754 (5)	0.2202 (4)	0.0449 (11)
H14A	−0.6635	0.6660	0.1619	0.054*
C15	−0.5634 (7)	0.7937 (5)	0.3021 (4)	0.0491 (12)
H15A	−0.6028	0.8646	0.3003	0.059*
C16	−0.4675 (7)	0.8076 (4)	0.3869 (4)	0.0469 (12)
H16A	−0.4391	0.8897	0.4408	0.056*
C17	−0.4550 (6)	0.5890 (4)	0.3143 (3)	0.0345 (9)
C18	−0.4036 (6)	0.4815 (4)	0.3297 (3)	0.0336 (9)
C19	0.1568 (7)	0.8271 (5)	1.0427 (4)	0.0454 (11)
C20	0.0882 (6)	0.7361 (4)	0.9360 (3)	0.0374 (10)
C21	0.0985 (7)	0.6051 (5)	0.9002 (4)	0.0456 (11)
H21A	0.1474	0.5744	0.9426	0.055*
C22	0.0371 (7)	0.5205 (5)	0.8029 (4)	0.0486 (12)
H22A	0.0477	0.4335	0.7788	0.058*
C23	−0.0412 (7)	0.5655 (5)	0.7404 (4)	0.0441 (11)
H23A	−0.0831	0.5081	0.6744	0.053*
C24	−0.0572 (6)	0.6956 (4)	0.7756 (3)	0.0352 (9)
C25	0.0095 (6)	0.7805 (4)	0.8736 (3)	0.0364 (9)
H25A	0.0013	0.8680	0.8978	0.044*
C26	−0.1412 (6)	0.7470 (4)	0.7111 (3)	0.0370 (10)
N1	−0.3230 (5)	0.5117 (4)	0.4209 (3)	0.0382 (8)
N2	−0.4136 (5)	0.7078 (3)	0.3947 (3)	0.0390 (8)
N3	−0.5463 (5)	0.2151 (3)	0.0821 (3)	0.0372 (8)
N4	−0.6549 (5)	0.4244 (4)	0.0569 (3)	0.0389 (8)
N5	0.0836 (6)	0.8341 (4)	0.4567 (3)	0.0484 (10)
O1	0.2191 (6)	0.7958 (4)	1.1021 (3)	0.0698 (12)
O2	0.1382 (6)	0.9481 (3)	1.0633 (2)	0.0592 (10)
H2B	0.1490	0.9896	1.1243	0.089*
O3	−0.1920 (5)	0.6681 (3)	0.6212 (2)	0.0463 (8)
O4	−0.1588 (5)	0.8630 (3)	0.7480 (2)	0.0508 (9)
O5	0.2236 (7)	0.8977 (5)	0.5054 (4)	0.0954 (17)
O6	0.0214 (9)	0.8751 (6)	0.4026 (5)	0.113 (2)
O7	0.0063 (5)	0.7317 (4)	0.4652 (4)	0.0729 (12)
O1W	−0.2595 (6)	0.8908 (3)	0.5905 (2)	0.0525 (9)
H1WA	−0.211 (8)	0.953 (4)	0.574 (4)	0.079*
H1WB	−0.250 (8)	0.915 (5)	0.6533 (16)	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0579 (4)	0.0285 (3)	0.0284 (3)	0.0089 (2)	0.0000 (2)	0.0082 (2)
C1	0.061 (3)	0.037 (2)	0.034 (2)	0.014 (2)	−0.003 (2)	0.0122 (19)
C2	0.077 (4)	0.036 (2)	0.037 (2)	0.022 (2)	−0.004 (2)	0.012 (2)
C3	0.053 (3)	0.035 (2)	0.040 (2)	0.018 (2)	−0.002 (2)	0.0102 (19)
C4	0.038 (2)	0.030 (2)	0.036 (2)	0.0091 (18)	0.0024 (18)	0.0132 (17)
C5	0.038 (2)	0.033 (2)	0.031 (2)	0.0103 (18)	0.0010 (17)	0.0112 (17)
C6	0.039 (2)	0.037 (2)	0.034 (2)	0.0111 (19)	0.0034 (18)	0.0112 (18)
C7	0.054 (3)	0.035 (2)	0.036 (2)	0.014 (2)	0.000 (2)	0.0080 (19)
C8	0.061 (3)	0.043 (3)	0.036 (2)	0.016 (2)	−0.004 (2)	0.004 (2)
C9	0.055 (3)	0.052 (3)	0.030 (2)	0.012 (2)	−0.009 (2)	0.009 (2)
C10	0.061 (3)	0.046 (3)	0.039 (2)	0.014 (2)	−0.006 (2)	0.017 (2)
C11	0.045 (3)	0.039 (2)	0.028 (2)	0.006 (2)	−0.0012 (18)	0.0119 (18)
C12	0.040 (2)	0.032 (2)	0.032 (2)	0.0112 (18)	0.0012 (18)	0.0120 (17)
C13	0.043 (3)	0.029 (2)	0.039 (2)	0.0076 (18)	0.0063 (19)	0.0141 (18)
C14	0.058 (3)	0.039 (2)	0.040 (2)	0.017 (2)	−0.002 (2)	0.016 (2)
C15	0.070 (3)	0.033 (2)	0.048 (3)	0.022 (2)	0.001 (2)	0.014 (2)
C16	0.060 (3)	0.031 (2)	0.043 (3)	0.013 (2)	−0.006 (2)	0.0077 (19)
C17	0.043 (3)	0.027 (2)	0.033 (2)	0.0094 (18)	0.0053 (18)	0.0111 (17)
C18	0.039 (2)	0.032 (2)	0.031 (2)	0.0107 (18)	0.0029 (17)	0.0120 (17)
C19	0.058 (3)	0.044 (3)	0.038 (2)	0.022 (2)	0.007 (2)	0.016 (2)
C20	0.045 (3)	0.036 (2)	0.034 (2)	0.0164 (19)	0.0066 (19)	0.0137 (18)
C21	0.058 (3)	0.042 (2)	0.043 (3)	0.023 (2)	0.006 (2)	0.017 (2)
C22	0.064 (3)	0.036 (2)	0.044 (3)	0.020 (2)	0.005 (2)	0.009 (2)
C23	0.053 (3)	0.036 (2)	0.038 (2)	0.013 (2)	0.006 (2)	0.0075 (19)
C24	0.042 (2)	0.032 (2)	0.030 (2)	0.0073 (18)	0.0031 (18)	0.0116 (17)
C25	0.045 (3)	0.031 (2)	0.032 (2)	0.0123 (18)	0.0029 (18)	0.0100 (17)
C26	0.047 (3)	0.032 (2)	0.030 (2)	0.0065 (19)	0.0021 (18)	0.0119 (17)
N1	0.050 (2)	0.0337 (18)	0.0276 (17)	0.0102 (16)	−0.0008 (16)	0.0085 (15)
N2	0.049 (2)	0.0276 (17)	0.0358 (19)	0.0090 (16)	0.0033 (17)	0.0078 (15)
N3	0.045 (2)	0.0322 (18)	0.0342 (19)	0.0120 (16)	0.0000 (16)	0.0114 (15)
N4	0.047 (2)	0.0344 (19)	0.0336 (19)	0.0096 (16)	0.0002 (16)	0.0124 (15)
N5	0.054 (3)	0.041 (2)	0.057 (3)	0.015 (2)	0.009 (2)	0.023 (2)
O1	0.104 (3)	0.067 (3)	0.047 (2)	0.045 (2)	−0.011 (2)	0.0204 (19)
O2	0.101 (3)	0.0427 (19)	0.0304 (17)	0.024 (2)	−0.0060 (18)	0.0078 (15)
O3	0.074 (2)	0.0329 (16)	0.0273 (15)	0.0122 (16)	−0.0032 (15)	0.0083 (12)
O4	0.085 (3)	0.0340 (16)	0.0269 (15)	0.0175 (17)	−0.0052 (16)	0.0045 (13)
O5	0.079 (3)	0.071 (3)	0.118 (4)	−0.008 (3)	−0.017 (3)	0.035 (3)
O6	0.140 (5)	0.120 (5)	0.116 (5)	0.035 (4)	−0.009 (4)	0.086 (4)
O7	0.062 (3)	0.056 (2)	0.117 (4)	0.015 (2)	0.021 (2)	0.052 (3)
O1W	0.090 (3)	0.0293 (16)	0.0361 (17)	0.0128 (17)	−0.0001 (18)	0.0122 (14)

Geometric parameters (Å, º) top

Cu1—O1W	1.952 (3)	C14—C15	1.370 (7)
Cu1—O3	1.960 (3)	C14—H14A	0.9300
Cu1—N1	2.000 (4)	C15—C16	1.373 (7)
Cu1—N2	2.001 (4)	C15—H15A	0.9300
Cu1—O7	2.284 (4)	C16—N2	1.331 (6)
C1—N1	1.336 (6)	C16—H16A	0.9300
C1—C2	1.381 (6)	C17—N2	1.363 (5)
C1—H1A	0.9300	C17—C18	1.454 (6)
C2—C3	1.374 (6)	C18—N1	1.343 (5)
C2—H2A	0.9300	C19—O1	1.188 (6)
C3—C4	1.403 (6)	C19—O2	1.324 (6)
C3—H3A	0.9300	C19—C20	1.501 (7)
C4—C18	1.392 (6)	C20—C21	1.387 (6)
C4—C5	1.452 (6)	C20—C25	1.389 (6)
C5—N3	1.327 (5)	C21—C22	1.371 (7)
C5—C12	1.426 (6)	C21—H21A	0.9300
C6—N3	1.352 (5)	C22—C23	1.394 (7)
C6—C11	1.409 (6)	C22—H22A	0.9300
C6—C7	1.418 (6)	C23—C24	1.393 (6)
C7—C8	1.346 (7)	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.387 (6)
C8—C9	1.400 (7)	C24—C26	1.491 (6)
C8—H8A	0.9300	C25—H25A	0.9300
C9—C10	1.355 (7)	C26—O4	1.250 (5)
C9—H9A	0.9300	C26—O3	1.261 (5)
C10—C11	1.425 (6)	N5—O6	1.201 (6)
C10—H10A	0.9300	N5—O5	1.215 (6)
C11—N4	1.358 (5)	N5—O7	1.236 (5)
C12—N4	1.310 (6)	O2—H2B	0.8200
C12—C13	1.458 (6)	O1W—H1WA	0.841 (19)
C13—C17	1.372 (6)	O1W—H1WB	0.842 (19)
C13—C14	1.402 (6)

O1W—Cu1—O3	94.58 (14)	C14—C15—H15A	120.0
O1W—Cu1—N1	171.25 (17)	C16—C15—H15A	120.0
O3—Cu1—N1	89.65 (14)	N2—C16—C15	122.3 (4)
O1W—Cu1—N2	92.03 (15)	N2—C16—H16A	118.9
O3—Cu1—N2	164.17 (16)	C15—C16—H16A	118.9
N1—Cu1—N2	82.02 (15)	N2—C17—C13	123.4 (4)
O1W—Cu1—O7	97.54 (17)	N2—C17—C18	115.2 (4)
O3—Cu1—O7	89.57 (16)	C13—C17—C18	121.4 (4)
N1—Cu1—O7	90.14 (16)	N1—C18—C4	123.9 (4)
N2—Cu1—O7	103.82 (17)	N1—C18—C17	116.1 (4)
N1—C1—C2	122.1 (4)	C4—C18—C17	120.0 (4)
N1—C1—H1A	119.0	O1—C19—O2	123.7 (5)
C2—C1—H1A	119.0	O1—C19—C20	125.0 (5)
C3—C2—C1	119.4 (4)	O2—C19—C20	111.3 (4)
C3—C2—H2A	120.3	C21—C20—C25	119.6 (4)
C1—C2—H2A	120.3	C21—C20—C19	119.7 (4)
C2—C3—C4	120.0 (4)	C25—C20—C19	120.7 (4)
C2—C3—H3A	120.0	C22—C21—C20	120.6 (5)
C4—C3—H3A	120.0	C22—C21—H21A	119.7
C18—C4—C3	116.3 (4)	C20—C21—H21A	119.7
C18—C4—C5	119.5 (4)	C21—C22—C23	119.6 (4)
C3—C4—C5	124.2 (4)	C21—C22—H22A	120.2
N3—C5—C12	122.1 (4)	C23—C22—H22A	120.2
N3—C5—C4	118.1 (4)	C24—C23—C22	120.7 (4)
C12—C5—C4	119.8 (4)	C24—C23—H23A	119.6
N3—C6—C11	121.4 (4)	C22—C23—H23A	119.6
N3—C6—C7	119.3 (4)	C25—C24—C23	118.7 (4)
C11—C6—C7	119.2 (4)	C25—C24—C26	119.1 (4)
C8—C7—C6	119.6 (4)	C23—C24—C26	122.2 (4)
C8—C7—H7A	120.2	C24—C25—C20	120.7 (4)
C6—C7—H7A	120.2	C24—C25—H25A	119.6
C7—C8—C9	122.0 (4)	C20—C25—H25A	119.6
C7—C8—H8A	119.0	O4—C26—O3	123.8 (4)
C9—C8—H8A	119.0	O4—C26—C24	119.4 (4)
C10—C9—C8	120.1 (4)	O3—C26—C24	116.8 (4)
C10—C9—H9A	119.9	C1—N1—C18	118.3 (4)
C8—C9—H9A	119.9	C1—N1—Cu1	128.4 (3)
C9—C10—C11	120.1 (5)	C18—N1—Cu1	113.1 (3)
C9—C10—H10A	120.0	C16—N2—C17	117.7 (4)
C11—C10—H10A	120.0	C16—N2—Cu1	129.4 (3)
N4—C11—C6	121.7 (4)	C17—N2—Cu1	112.9 (3)
N4—C11—C10	119.3 (4)	C5—N3—C6	116.1 (4)
C6—C11—C10	119.0 (4)	C12—N4—C11	116.4 (4)
N4—C12—C5	122.1 (4)	O6—N5—O5	118.2 (5)
N4—C12—C13	118.4 (4)	O6—N5—O7	121.5 (5)
C5—C12—C13	119.5 (4)	O5—N5—O7	120.3 (5)
C17—C13—C14	117.5 (4)	C19—O2—H2B	109.5
C17—C13—C12	119.5 (4)	C26—O3—Cu1	128.9 (3)
C14—C13—C12	123.0 (4)	N5—O7—Cu1	121.6 (3)
C15—C14—C13	119.0 (4)	Cu1—O1W—H1WA	123 (4)
C15—C14—H14A	120.5	Cu1—O1W—H1WB	117 (4)
C13—C14—H14A	120.5	H1WA—O1W—H1WB	111 (3)
C14—C15—C16	120.1 (4)

N1—C1—C2—C3	2.4 (8)	C26—C24—C25—C20	179.9 (4)
C1—C2—C3—C4	−0.3 (8)	C21—C20—C25—C24	−0.8 (7)
C2—C3—C4—C18	−2.2 (7)	C19—C20—C25—C24	−178.7 (4)
C2—C3—C4—C5	178.2 (5)	C25—C24—C26—O4	−4.0 (7)
C18—C4—C5—N3	174.7 (4)	C23—C24—C26—O4	176.9 (5)
C3—C4—C5—N3	−5.6 (7)	C25—C24—C26—O3	176.6 (4)
C18—C4—C5—C12	−5.8 (6)	C23—C24—C26—O3	−2.5 (7)
C3—C4—C5—C12	173.9 (4)	C2—C1—N1—C18	−1.7 (7)
N3—C6—C7—C8	176.6 (5)	C2—C1—N1—Cu1	−177.8 (4)
C11—C6—C7—C8	−2.3 (7)	C4—C18—N1—C1	−1.0 (7)
C6—C7—C8—C9	1.1 (8)	C17—C18—N1—C1	177.3 (4)
C7—C8—C9—C10	0.4 (9)	C4—C18—N1—Cu1	175.7 (4)
C8—C9—C10—C11	−0.6 (8)	C17—C18—N1—Cu1	−6.1 (5)
N3—C6—C11—N4	2.5 (7)	O3—Cu1—N1—C1	−10.2 (4)
C7—C6—C11—N4	−178.7 (4)	N2—Cu1—N1—C1	−176.7 (4)
N3—C6—C11—C10	−176.8 (4)	O7—Cu1—N1—C1	79.3 (4)
C7—C6—C11—C10	2.0 (7)	O3—Cu1—N1—C18	173.5 (3)
C9—C10—C11—N4	−179.9 (5)	N2—Cu1—N1—C18	7.0 (3)
C9—C10—C11—C6	−0.6 (8)	O7—Cu1—N1—C18	−96.9 (3)
N3—C5—C12—N4	1.5 (7)	C15—C16—N2—C17	0.8 (8)
C4—C5—C12—N4	−178.0 (4)	C15—C16—N2—Cu1	179.2 (4)
N3—C5—C12—C13	−178.5 (4)	C13—C17—N2—C16	2.0 (7)
C4—C5—C12—C13	2.0 (6)	C18—C17—N2—C16	−175.8 (4)
N4—C12—C13—C17	−176.8 (4)	C13—C17—N2—Cu1	−176.7 (4)
C5—C12—C13—C17	3.1 (7)	C18—C17—N2—Cu1	5.5 (5)
N4—C12—C13—C14	3.7 (7)	O1W—Cu1—N2—C16	1.2 (5)
C5—C12—C13—C14	−176.3 (4)	O3—Cu1—N2—C16	115.8 (6)
C17—C13—C14—C15	0.9 (7)	N1—Cu1—N2—C16	174.7 (5)
C12—C13—C14—C15	−179.6 (5)	O7—Cu1—N2—C16	−97.1 (5)
C13—C14—C15—C16	1.6 (8)	O1W—Cu1—N2—C17	179.7 (3)
C14—C15—C16—N2	−2.6 (9)	O3—Cu1—N2—C17	−65.7 (6)
C14—C13—C17—N2	−2.8 (7)	N1—Cu1—N2—C17	−6.8 (3)
C12—C13—C17—N2	177.7 (4)	O7—Cu1—N2—C17	81.4 (3)
C14—C13—C17—C18	174.9 (4)	C12—C5—N3—C6	−1.0 (6)
C12—C13—C17—C18	−4.6 (7)	C4—C5—N3—C6	178.5 (4)
C3—C4—C18—N1	2.9 (7)	C11—C6—N3—C5	−0.9 (6)
C5—C4—C18—N1	−177.4 (4)	C7—C6—N3—C5	−179.7 (4)
C3—C4—C18—C17	−175.3 (4)	C5—C12—N4—C11	0.1 (7)
C5—C4—C18—C17	4.4 (6)	C13—C12—N4—C11	−179.9 (4)
N2—C17—C18—N1	0.4 (6)	C6—C11—N4—C12	−2.0 (7)
C13—C17—C18—N1	−177.5 (4)	C10—C11—N4—C12	177.3 (4)
N2—C17—C18—C4	178.7 (4)	O4—C26—O3—Cu1	11.6 (7)
C13—C17—C18—C4	0.8 (7)	C24—C26—O3—Cu1	−169.0 (3)
O1—C19—C20—C21	−1.2 (8)	O1W—Cu1—O3—C26	−4.4 (4)
O2—C19—C20—C21	179.2 (5)	N1—Cu1—O3—C26	−176.7 (4)
O1—C19—C20—C25	176.7 (5)	N2—Cu1—O3—C26	−118.7 (6)
O2—C19—C20—C25	−2.9 (7)	O7—Cu1—O3—C26	93.1 (4)
C25—C20—C21—C22	2.3 (8)	O6—N5—O7—Cu1	−54.7 (7)
C19—C20—C21—C22	−179.8 (5)	O5—N5—O7—Cu1	123.5 (5)
C20—C21—C22—C23	−2.0 (8)	O1W—Cu1—O7—N5	−30.2 (5)
C21—C22—C23—C24	0.2 (8)	O3—Cu1—O7—N5	−124.7 (4)
C22—C23—C24—C25	1.3 (7)	N1—Cu1—O7—N5	145.6 (4)
C22—C23—C24—C26	−179.6 (5)	N2—Cu1—O7—N5	63.8 (5)
C23—C24—C25—C20	−1.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O6ⁱ	0.84 (2)	2.08 (3)	2.856 (7)	153 (5)
O1W—H1WA···O5ⁱ	0.84 (2)	2.41 (3)	3.165 (6)	151 (6)
O1W—H1WB···O4	0.84 (2)	1.88 (4)	2.565 (5)	138 (6)
O2—H2B···O4ⁱⁱ	0.82	1.94	2.722 (4)	159

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₅O₄)(NO₃)(C₁₈H₁₀N₄)(H₂O)]
M_r	590.99
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8965 (17), 11.295 (4), 14.533 (6)
α, β, γ (°)	112.73 (3), 90.94 (3), 102.60 (2)
V (Å³)	1159.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.37 × 0.32 × 0.24

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.707, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	6320, 5180, 3353
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.198, 1.02
No. of reflections	5180
No. of parameters	367
No. of restraints	39
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.92

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O1W	1.952 (3)	Cu1—N2	2.001 (4)
Cu1—O3	1.960 (3)	Cu1—O7	2.284 (4)
Cu1—N1	2.000 (4)

O1W—Cu1—O3	94.58 (14)	N1—Cu1—N2	82.02 (15)
O1W—Cu1—N1	171.25 (17)	O1W—Cu1—O7	97.54 (17)
O3—Cu1—N1	89.65 (14)	O3—Cu1—O7	89.57 (16)
O1W—Cu1—N2	92.03 (15)	N1—Cu1—O7	90.14 (16)
O3—Cu1—N2	164.17 (16)	N2—Cu1—O7	103.82 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O6ⁱ	0.841 (19)	2.08 (3)	2.856 (7)	153 (5)
O1W—H1WA···O5ⁱ	0.841 (19)	2.41 (3)	3.165 (6)	151 (6)
O1W—H1WB···O4	0.842 (19)	1.88 (4)	2.565 (5)	138 (6)
O2—H2B···O4ⁱⁱ	0.82	1.94	2.722 (4)	159

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+2, −z+2.

Acknowledgements

This work was supported by the Project of Shanghai Municipal Education Commission (2008068, 2008080).

References

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