(2-Hy­droxy­acetato-κO1)bis­(1,10-phenan­throline-κ2N,N′)copper(II) nitrate

Kong, Y.-J.; Yuan, Z.-D.

doi:10.1107/S1600536811013110

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m592

doi:10.1107/S1600536811013110

Open

access

(2-Hydroxyacetato-κO¹)bis(1,10-phenanthroline-κ²N,N′)copper(II) nitrate

Ya-Jie Kong ^a ^* and Zhuang-Dong Yuan ^a

^aDepartment of Chemistry and Chemical Engineering, Jining University, Qufu 273155, Shandong, People's Republic of China
^*Correspondence e-mail: kongyaj@jnxy.edu.cn

(Received 13 March 2011; accepted 7 April 2011; online 13 April 2011)

In the title compound, [Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃, the Cu^II atom is coordinated by two phenanthroline (phen) ligands and one carboxyl-O atom of a hydroxyacetate anion in a distorted square-pyramidal geometry. The hydroxy group of the hydroxyacetate ligand links with the counter NO₃⁻ anion via a pair of bifurcated O—H⋯O hydrogen bonds. The centroid–centroid distance of 3.5676 (14) Å between benzene rings of parallel phen ligands of adjacent molecules suggests the existence of π–π stacking. Weak intermolecular C—H⋯O hydrogen bonding is also present in the crystal structure.

Related literature

For related structures, see: Carballo et al. (2001 ).

Experimental

Crystal data

[Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃
M_r = 561.00
Monoclinic, C 2/c
a = 21.718 (4) Å
b = 14.347 (3) Å
c = 16.311 (3) Å
β = 117.045 (3)°
V = 4526.5 (16) Å³
Z = 8
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.50 × 0.40 × 0.40 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.599, T_max = 0.664
17009 measured reflections
4425 independent reflections
4047 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.101
S = 1.06
4425 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O4	1.9511 (15)
Cu1—N1	2.0109 (16)
Cu1—N2	2.2298 (16)
Cu1—N3	2.0037 (16)
Cu1—N4	2.0449 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1	0.82	2.15	2.963 (3)	168
O6—H6A⋯O3	0.82	2.49	3.135 (4)	137
C7—H7A⋯O3ⁱ	0.93	2.42	3.351 (3)	176
C16—H16A⋯O1ⁱⁱ	0.93	2.53	3.383 (4)	152
C18—H18A⋯O3ⁱⁱⁱ	0.93	2.53	3.456 (4)	172
C26—H26A⋯O6^iv	0.97	2.44	3.297 (3)	147
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013110/xu5175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013110/xu5175Isup2.hkl

checkCIF report

Comment top

The molecules [Cu(C₁₂H₈N₂)₂(C₂H₃O₃)] in three different solvents or anions(2-hydroxyacetate anion, 2-hydroxyacetic acid and acetonitrile solvent) have been reported (Carballo et al., 2001).

Crystals [Cu(C₁₂H₈N₂)₂(C₂H₃O₃)]NO₃ (I) were obtained by crystallized from ethanol-water solution. The molecular structure of (I) is shown in Fig. 1. In the title compound the Cu^II atom is coordinated by two phenanthroline (phen) ligands and one carboxyl-O atom of a hydroxyacetate anion in a distorted square-pyramidal geometry (Table 1). The hydroxy group of the hydroxyacetate ligand links with the counter NO₃^- anion via a pair of bifurcated O—H···O hydrogen bonds (Table 2). The centroid-to-centroid distance of 3.5676 (14) Å between benzene rings of parallel phen ligands of adjacent molecules suggests the existence of π-π stacking. Weak intermolecular C—H···O hydrogen bonding is also present in the crystal structure.

Related literature top

For related structures, see: Carballo et al. (2001).

Experimental top

Copper nitrate (0.093 g, 0.5 mmol) was added to a mixed solution of hydroxyacetic acid (0.076 g, 1 mmol) in distilled water (10 ml) and 1,10-phenanthroline (0.090 g, 0.5 mmol) in ethanol (5 ml). The pH value of the mixture was adjusted to 7 with ammonia. The resulting solution was stirred for 1 h, and then filtered off. The filtrate was left to evaporate showly at room temperature. After a long time, blue block crystals were obtained.

Computing details top

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

Figures top

	Fig. 1. Molecular structure of the title compound drawn with displacement ellipsoids at the 30% probability level. All hydrogen atoms have been omitted for clarity.
	Fig. 2. Part of an one-dimensional linear chains of the title compound.

(2-Hydroxyacetato-κO¹)bis(1,10-phenanthroline- κ²N,N')copper(II) nitrate top

Crystal data top

[Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃	F(000) = 2296
M_r = 561.00	D_x = 1.646 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5502 reflections
a = 21.718 (4) Å	θ = 2.5–28.2°
b = 14.347 (3) Å	µ = 1.02 mm⁻¹
c = 16.311 (3) Å	T = 293 K
β = 117.045 (3)°	Block, blue
V = 4526.5 (16) Å³	0.50 × 0.40 × 0.40 mm
Z = 8

Data collection top

Bruker SMART 1000 diffractometer	4425 independent reflections
Radiation source: fine-focus sealed tube	4047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω–scan	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −26→26
T_min = 0.599, T_max = 0.664	k = −17→17
17009 measured reflections	l = −20→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0711P)² + 1.7595P] where P = (F_o² + 2F_c²)/3
4425 reflections	(Δ/σ)_max = 0.002
343 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃	V = 4526.5 (16) Å³
M_r = 561.00	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.718 (4) Å	µ = 1.02 mm⁻¹
b = 14.347 (3) Å	T = 293 K
c = 16.311 (3) Å	0.50 × 0.40 × 0.40 mm
β = 117.045 (3)°

Data collection top

Bruker SMART 1000 diffractometer	4425 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4047 reflections with I > 2σ(I)
T_min = 0.599, T_max = 0.664	R_int = 0.024
17009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	Δρ_max = 0.53 e Å⁻³
4425 reflections	Δρ_min = −0.23 e Å⁻³
343 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	0.352559 (11)	0.810948 (15)	0.864386 (15)	0.03488 (11)
C2	0.51483 (12)	0.63868 (16)	0.86753 (16)	0.0520 (5)
H2A	0.5233	0.5752	0.8673	0.062*
C12	0.51725 (10)	0.98715 (15)	0.87161 (13)	0.0431 (4)
C23	0.33565 (9)	0.80523 (11)	1.02687 (13)	0.0328 (4)
C11	0.47143 (9)	0.91941 (13)	0.87363 (12)	0.0352 (4)
C24	0.34342 (10)	0.78875 (14)	1.11575 (13)	0.0374 (4)
C13	0.23293 (10)	0.93864 (14)	0.82592 (14)	0.0442 (4)
H13A	0.2283	0.9456	0.7667	0.053*
C25	0.27347 (10)	0.74094 (14)	0.69714 (13)	0.0403 (4)
C9	0.48683 (10)	0.82262 (13)	0.87109 (12)	0.0356 (4)
C21	0.28533 (9)	0.86956 (12)	0.96824 (12)	0.0338 (4)
C17	0.30025 (11)	0.83895 (17)	1.14532 (14)	0.0458 (5)
H17A	0.3049	0.8286	1.2041	0.055*
C14	0.19071 (11)	0.99126 (15)	0.85214 (16)	0.0508 (5)
H14A	0.1590	1.0331	0.8110	0.061*
C22	0.24435 (9)	0.91847 (13)	0.99943 (14)	0.0396 (4)
C20	0.42130 (10)	0.70152 (13)	1.04555 (14)	0.0406 (4)
H20A	0.4485	0.6717	1.0229	0.049*
C19	0.43112 (11)	0.67978 (14)	1.13422 (15)	0.0454 (5)
H19A	0.4638	0.6354	1.1690	0.055*
C1	0.45271 (12)	0.66987 (14)	0.86349 (15)	0.0444 (5)
H1A	0.4197	0.6262	0.8589	0.053*
C8	0.39708 (12)	1.02971 (15)	0.87769 (16)	0.0486 (5)
H8A	0.3566	1.0450	0.8807	0.058*
C18	0.39312 (11)	0.72315 (15)	1.16947 (13)	0.0442 (4)
H18A	0.4000	0.7095	1.2288	0.053*
C10	0.54928 (11)	0.79679 (15)	0.87236 (14)	0.0428 (4)
C6	0.49801 (12)	1.07989 (15)	0.87063 (15)	0.0524 (5)
H6B	0.5262	1.1272	0.8676	0.063*
C16	0.25344 (10)	0.90029 (15)	1.09058 (14)	0.0464 (5)
H16A	0.2262	0.9318	1.1120	0.056*
C15	0.19623 (11)	0.98105 (14)	0.93763 (16)	0.0478 (5)
H15A	0.1680	1.0156	0.9553	0.057*
C26	0.22641 (12)	0.73763 (16)	0.59474 (14)	0.0500 (5)
H26A	0.2470	0.6967	0.5666	0.060*
H26B	0.1828	0.7101	0.5848	0.060*
C4	0.59588 (11)	0.86792 (17)	0.87278 (15)	0.0525 (5)
H4A	0.6378	0.8512	0.8744	0.063*
C5	0.57971 (11)	0.95780 (17)	0.87093 (16)	0.0541 (5)
H5A	0.6100	1.0026	0.8691	0.065*
C7	0.43853 (12)	1.10155 (15)	0.87403 (16)	0.0548 (5)
H7A	0.4257	1.1634	0.8739	0.066*
C3	0.56297 (12)	0.70205 (16)	0.87188 (17)	0.0512 (5)
H3A	0.6046	0.6822	0.8745	0.061*
O4	0.30007 (8)	0.81909 (10)	0.73072 (10)	0.0469 (4)
O5	0.28331 (10)	0.66929 (11)	0.74203 (12)	0.0583 (4)
O6	0.21298 (10)	0.82300 (12)	0.54982 (11)	0.0608 (4)
H6A	0.1892	0.8549	0.5662	0.091*
O1	0.12811 (12)	0.95952 (15)	0.59033 (16)	0.0832 (6)
O3	0.10001 (14)	0.82669 (13)	0.61923 (19)	0.0869 (7)
O2	0.05765 (12)	0.94510 (15)	0.6477 (2)	0.0971 (8)
N4	0.37498 (8)	0.76262 (10)	0.99287 (10)	0.0341 (3)
N1	0.43912 (8)	0.75916 (11)	0.86593 (10)	0.0372 (3)
N2	0.41221 (8)	0.94125 (11)	0.87707 (11)	0.0391 (3)
N3	0.27921 (8)	0.87939 (11)	0.88243 (10)	0.0366 (3)
N5	0.09405 (10)	0.91099 (13)	0.61673 (14)	0.0516 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03761 (16)	0.03582 (16)	0.03405 (16)	0.00062 (8)	0.01877 (12)	0.00072 (8)
C2	0.0573 (12)	0.0443 (11)	0.0552 (13)	0.0108 (10)	0.0263 (10)	−0.0026 (9)
C12	0.0409 (10)	0.0465 (11)	0.0359 (10)	−0.0102 (8)	0.0122 (8)	−0.0016 (8)
C23	0.0316 (8)	0.0329 (9)	0.0347 (9)	−0.0083 (6)	0.0159 (7)	−0.0041 (6)
C11	0.0379 (9)	0.0373 (9)	0.0278 (8)	−0.0050 (7)	0.0127 (7)	−0.0013 (7)
C24	0.0376 (9)	0.0391 (9)	0.0365 (9)	−0.0110 (8)	0.0178 (8)	−0.0041 (7)
C13	0.0436 (10)	0.0413 (10)	0.0450 (10)	0.0025 (8)	0.0178 (9)	0.0084 (8)
C25	0.0436 (10)	0.0472 (11)	0.0406 (10)	0.0035 (8)	0.0284 (8)	0.0006 (8)
C9	0.0373 (9)	0.0403 (10)	0.0286 (9)	−0.0014 (7)	0.0145 (7)	−0.0008 (7)
C21	0.0317 (8)	0.0327 (9)	0.0373 (9)	−0.0066 (7)	0.0158 (7)	−0.0043 (7)
C17	0.0458 (11)	0.0577 (12)	0.0412 (11)	−0.0122 (10)	0.0263 (9)	−0.0100 (9)
C14	0.0448 (11)	0.0360 (10)	0.0650 (14)	0.0057 (8)	0.0191 (10)	0.0062 (9)
C22	0.0349 (9)	0.0360 (9)	0.0489 (10)	−0.0049 (7)	0.0199 (8)	−0.0097 (8)
C20	0.0391 (10)	0.0395 (10)	0.0410 (10)	0.0030 (8)	0.0165 (8)	0.0013 (8)
C19	0.0464 (11)	0.0420 (11)	0.0402 (11)	0.0017 (8)	0.0129 (9)	0.0069 (8)
C1	0.0518 (12)	0.0350 (10)	0.0487 (12)	0.0000 (8)	0.0247 (10)	−0.0013 (8)
C8	0.0491 (11)	0.0383 (11)	0.0569 (12)	0.0001 (9)	0.0228 (10)	−0.0034 (9)
C18	0.0478 (11)	0.0484 (11)	0.0338 (9)	−0.0102 (9)	0.0162 (8)	0.0029 (8)
C10	0.0390 (10)	0.0529 (11)	0.0356 (10)	0.0004 (8)	0.0162 (8)	−0.0034 (8)
C6	0.0542 (12)	0.0420 (11)	0.0502 (12)	−0.0171 (9)	0.0145 (10)	−0.0017 (9)
C16	0.0432 (10)	0.0530 (12)	0.0498 (11)	−0.0073 (9)	0.0271 (9)	−0.0155 (9)
C15	0.0431 (10)	0.0380 (10)	0.0617 (13)	0.0004 (8)	0.0234 (10)	−0.0086 (9)
C26	0.0539 (12)	0.0556 (13)	0.0425 (11)	−0.0028 (10)	0.0237 (9)	−0.0058 (9)
C4	0.0373 (10)	0.0688 (15)	0.0522 (12)	−0.0069 (10)	0.0210 (9)	−0.0061 (10)
C5	0.0443 (11)	0.0633 (14)	0.0541 (13)	−0.0191 (10)	0.0218 (10)	−0.0041 (10)
C7	0.0629 (13)	0.0337 (10)	0.0582 (13)	−0.0044 (9)	0.0190 (11)	−0.0027 (9)
C3	0.0441 (11)	0.0582 (13)	0.0515 (13)	0.0086 (9)	0.0218 (10)	−0.0042 (10)
O4	0.0547 (9)	0.0491 (9)	0.0351 (7)	−0.0018 (6)	0.0188 (7)	−0.0006 (6)
O5	0.0761 (11)	0.0511 (9)	0.0560 (10)	0.0039 (8)	0.0374 (9)	0.0108 (7)
O6	0.0698 (11)	0.0724 (11)	0.0412 (8)	0.0117 (8)	0.0261 (8)	0.0105 (7)
O1	0.0908 (14)	0.0763 (13)	0.0973 (15)	−0.0311 (11)	0.0556 (13)	0.0017 (11)
O3	0.127 (2)	0.0480 (11)	0.1166 (19)	0.0048 (11)	0.0819 (17)	0.0051 (10)
O2	0.0933 (15)	0.0659 (13)	0.164 (3)	0.0014 (11)	0.0865 (18)	−0.0056 (13)
N4	0.0343 (7)	0.0347 (8)	0.0336 (7)	−0.0011 (6)	0.0156 (6)	−0.0004 (6)
N1	0.0416 (8)	0.0360 (8)	0.0384 (8)	−0.0003 (6)	0.0222 (7)	−0.0027 (6)
N2	0.0425 (8)	0.0340 (8)	0.0408 (8)	−0.0026 (6)	0.0189 (7)	−0.0018 (6)
N3	0.0356 (7)	0.0359 (8)	0.0383 (8)	−0.0005 (6)	0.0168 (6)	0.0021 (6)
N5	0.0493 (10)	0.0467 (10)	0.0585 (11)	−0.0076 (8)	0.0243 (9)	−0.0015 (8)

Geometric parameters (Å, º) top

Cu1—O4	1.9511 (15)	C22—C15	1.399 (3)
Cu1—N1	2.0109 (16)	C22—C16	1.432 (3)
Cu1—N2	2.2298 (16)	C20—N4	1.316 (2)
Cu1—N3	2.0037 (16)	C20—C19	1.398 (3)
Cu1—N4	2.0449 (15)	C20—H20A	0.9300
C2—C3	1.363 (4)	C19—C18	1.353 (3)
C2—C1	1.394 (3)	C19—H19A	0.9300
C2—H2A	0.9300	C1—N1	1.319 (3)
C12—C6	1.393 (3)	C1—H1A	0.9300
C12—C11	1.402 (3)	C8—N2	1.312 (3)
C12—C5	1.425 (3)	C8—C7	1.387 (3)
C23—N4	1.357 (2)	C8—H8A	0.9300
C23—C24	1.401 (3)	C18—H18A	0.9300
C23—C21	1.418 (3)	C10—C3	1.392 (3)
C11—N2	1.350 (2)	C10—C4	1.435 (3)
C11—C9	1.433 (3)	C6—C7	1.354 (3)
C24—C18	1.400 (3)	C6—H6B	0.9300
C24—C17	1.429 (3)	C16—H16A	0.9300
C13—N3	1.319 (3)	C15—H15A	0.9300
C13—C14	1.397 (3)	C26—O6	1.388 (3)
C13—H13A	0.9300	C26—H26A	0.9700
C25—O5	1.223 (3)	C26—H26B	0.9700
C25—O4	1.266 (2)	C4—C5	1.333 (3)
C25—C26	1.511 (3)	C4—H4A	0.9300
C9—N1	1.353 (2)	C5—H5A	0.9300
C9—C10	1.397 (3)	C7—H7A	0.9300
C21—N3	1.352 (2)	C3—H3A	0.9300
C21—C22	1.398 (2)	O6—H6A	0.8200
C17—C16	1.334 (3)	O1—N5	1.228 (3)
C17—H17A	0.9300	O3—N5	1.215 (3)
C14—C15	1.352 (3)	O2—N5	1.217 (3)
C14—H14A	0.9300

O4—Cu1—N3	92.02 (6)	C2—C1—H1A	118.8
O4—Cu1—N1	95.97 (6)	N2—C8—C7	123.3 (2)
N3—Cu1—N1	168.63 (6)	N2—C8—H8A	118.4
O4—Cu1—N4	155.70 (6)	C7—C8—H8A	118.4
N3—Cu1—N4	81.39 (6)	C19—C18—C24	119.28 (18)
N1—Cu1—N4	94.38 (6)	C19—C18—H18A	120.4
O4—Cu1—N2	94.19 (6)	C24—C18—H18A	120.4
N3—Cu1—N2	92.45 (6)	C3—C10—C9	117.9 (2)
N1—Cu1—N2	78.94 (6)	C3—C10—C4	122.8 (2)
N4—Cu1—N2	109.36 (6)	C9—C10—C4	119.3 (2)
C3—C2—C1	119.4 (2)	C7—C6—C12	120.4 (2)
C3—C2—H2A	120.3	C7—C6—H6B	119.8
C1—C2—H2A	120.3	C12—C6—H6B	119.8
C6—C12—C11	116.7 (2)	C17—C16—C22	121.22 (18)
C6—C12—C5	124.3 (2)	C17—C16—H16A	119.4
C11—C12—C5	118.9 (2)	C22—C16—H16A	119.4
N4—C23—C24	123.01 (17)	C14—C15—C22	119.98 (19)
N4—C23—C21	116.93 (16)	C14—C15—H15A	120.0
C24—C23—C21	120.06 (17)	C22—C15—H15A	120.0
N2—C11—C12	122.69 (18)	O6—C26—C25	115.45 (19)
N2—C11—C9	117.74 (16)	O6—C26—H26A	108.4
C12—C11—C9	119.57 (18)	C25—C26—H26A	108.4
C18—C24—C23	117.19 (18)	O6—C26—H26B	108.4
C18—C24—C17	124.43 (18)	C25—C26—H26B	108.4
C23—C24—C17	118.38 (19)	H26A—C26—H26B	107.5
N3—C13—C14	122.1 (2)	C5—C4—C10	120.6 (2)
N3—C13—H13A	118.9	C5—C4—H4A	119.7
C14—C13—H13A	118.9	C10—C4—H4A	119.7
O5—C25—O4	124.3 (2)	C4—C5—C12	121.8 (2)
O5—C25—C26	118.8 (2)	C4—C5—H5A	119.1
O4—C25—C26	116.88 (18)	C12—C5—H5A	119.1
N1—C9—C10	122.23 (18)	C6—C7—C8	118.7 (2)
N1—C9—C11	118.14 (17)	C6—C7—H7A	120.6
C10—C9—C11	119.62 (17)	C8—C7—H7A	120.6
N3—C21—C22	123.04 (17)	C2—C3—C10	119.4 (2)
N3—C21—C23	116.68 (16)	C2—C3—H3A	120.3
C22—C21—C23	120.28 (17)	C10—C3—H3A	120.3
C16—C17—C24	121.60 (19)	C25—O4—Cu1	110.50 (12)
C16—C17—H17A	119.2	C26—O6—H6A	109.5
C24—C17—H17A	119.2	C20—N4—C23	118.00 (16)
C15—C14—C13	119.6 (2)	C20—N4—Cu1	130.53 (13)
C15—C14—H14A	120.2	C23—N4—Cu1	111.43 (12)
C13—C14—H14A	120.2	C1—N1—C9	118.67 (17)
C21—C22—C15	116.77 (19)	C1—N1—Cu1	125.39 (14)
C21—C22—C16	118.44 (18)	C9—N1—Cu1	115.93 (12)
C15—C22—C16	124.77 (18)	C8—N2—C11	118.14 (17)
N4—C20—C19	122.40 (19)	C8—N2—Cu1	132.42 (15)
N4—C20—H20A	118.8	C11—N2—Cu1	109.03 (12)
C19—C20—H20A	118.8	C13—N3—C21	118.41 (17)
C18—C19—C20	120.10 (19)	C13—N3—Cu1	128.11 (14)
C18—C19—H19A	120.0	C21—N3—Cu1	112.99 (12)
C20—C19—H19A	120.0	O3—N5—O2	117.7 (2)
N1—C1—C2	122.4 (2)	O3—N5—O1	120.3 (2)
N1—C1—H1A	118.8	O2—N5—O1	121.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1	0.82	2.15	2.963 (3)	168
O6—H6A···O3	0.82	2.49	3.135 (4)	137
C7—H7A···O3ⁱ	0.93	2.42	3.351 (3)	176
C16—H16A···O1ⁱⁱ	0.93	2.53	3.383 (4)	152
C18—H18A···O3ⁱⁱⁱ	0.93	2.53	3.456 (4)	172
C26—H26A···O6^iv	0.97	2.44	3.297 (3)	147

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x, −y+2, z+1/2; (iii) −x+1/2, −y+3/2, −z+2; (iv) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃
M_r	561.00
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.718 (4), 14.347 (3), 16.311 (3)
β (°)	117.045 (3)
V (Å³)	4526.5 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.50 × 0.40 × 0.40

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.599, 0.664
No. of measured, independent and observed [I > 2σ(I)] reflections	17009, 4425, 4047
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.101, 1.06
No. of reflections	4425
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.23

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

Selected bond lengths (Å) top

Cu1—O4	1.9511 (15)	Cu1—N3	2.0037 (16)
Cu1—N1	2.0109 (16)	Cu1—N4	2.0449 (15)
Cu1—N2	2.2298 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1	0.82	2.15	2.963 (3)	168
O6—H6A···O3	0.82	2.49	3.135 (4)	137
C7—H7A···O3ⁱ	0.93	2.42	3.351 (3)	176
C16—H16A···O1ⁱⁱ	0.93	2.53	3.383 (4)	152
C18—H18A···O3ⁱⁱⁱ	0.93	2.53	3.456 (4)	172
C26—H26A···O6^iv	0.97	2.44	3.297 (3)	147

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x, −y+2, z+1/2; (iii) −x+1/2, −y+3/2, −z+2; (iv) −x+1/2, −y+3/2, −z+1.

Acknowledgements

This work was supported by the Science Foundation of Jining University, China.

References

Bruker. (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carballo, R., Covelo, B., Balboa, S., Castiñeiras, A. & Niclós, J. (2001). Z. Anorg. Allg. Chem. 627, 948–954. CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar