(2,2′-Bipyridine-κ2N,N′)(3,5-dinitro­salicylato-κ2O1,O2)(pyridine-κN)copper(II)

Wen, D.-C.; Wu, L.-H.; Zhong, C.-L.; Xie, T.-Y.; Ta, H.-G.

doi:10.1107/S1600536807039876

(2,2′-Bipyridine-κ²N,N′)(3,5-dinitrosalicylato-κ²O¹,O²)(pyridine-κN)copper(II)

D.-C. Wen, L.-H. Wu, C.-L. Zhong, T.-Y. Xie and H.-G. Ta

In the title compound, [Cu(C₇H₂N₂O₇)(C₅H₅N)(C₁₀H₈N₂)], the Cu^II atom is coordinated by two O atoms from a 3,5-dinitrosalicylate ligand, two N atoms from a 2,2′-bipyridine ligand and one N atom from a pyridine ligand in a square-pyramidal geometry. The structure is stabilized by C—H

O hydrogen bonds and π–π interactions between the bipyridine ligands, with a centroid–centroid distance between neighbouring aromatic rings of 3.96 (8) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039876/hy2074sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039876/hy2074Isup2.hkl Contains datablock I

CCDC reference: 660121

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R factor = 0.052
wR factor = 0.149
Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        200 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  O6      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A   ..  O5      ..       2.64 Ang.

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)       2.32

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

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

Comment top

Salicylic acid and its substituted derivatives continue to attract attention because of their versatile coordination modes (Thurston et al., 2004; Valigura et al., 2004; Wang & Okabe, 2004; Zhu et al., 2003) and biological applications (Lemoine et al., 2004). We report here the structure of a Cu^II complex with 3,5-dinitrosalicylic acid (He et al., 2005; He et al., 2006; Wen et al., 2007).

In the title complex, the Cu^II atom is bonded to two N atoms from a 2,2'-bipyridine ligand, one carboxylate O atom and one phenolato O atom from a 3,5-dinitrosalicylate ligand (Fig. 1). The coordination of the Cu^II atom is completed by bonding to a pyridine N atom in the axial direction, giving a square-pyramidal geometry (Table 1). The dihedral angle of the carboxylate group and the aromatic ring in 3,5-dinitrosalicylate ligand is 10.8 (9)°. The two rings in the 2,2'-bipyridine ligand are a little twisted relative to each other, with a dihedral angle of 2.2 (3)°. The adjacent mononuclear units are further connected to each other by C—H···O hydrogen bonds between the 2,2'-bipyridine (or pyridine) ligands and the O atoms from carboxylate and NO₂ groups of the 3,5-dinitrosalicylate ligands (Table 2), resulting in an extended three-dimensional structure (Fig. 2). The partially overlapped arrangement indicates π–π interactions between the approximately parallel 2,2'-bipyridine ligands (the contact distances: C12···C17^v = 3.45 (7), C11···C13^v = 3.55 (6), C10···C14^v = 3.55 (7) Å; symmetry code: (v) 1 - x, 1 - y, 2 - z). The centroid–centroid distance of aromatic rings of the neighboring 2,2'-bipyridine ligands is 3.96 (8) Å. The crystal structure is stabilized by C—H···O hydrogen bonds and π–π interactions.

Related literature top

For related literature, see: He et al. (2005, 2006); Lemoine et al. (2004); Thurston et al. (2004); Valigura et al. (2004); Wang & Okabe (2004); Wen et al. (2007); Zhu et al. (2003).

Experimental top

A mixture of Cu(NO₃)₂.4H₂O (0.026 g, 0.1 mmol), 2,2'-bipyridine (0.016 g, 0.1 mmol), 3,5-dinitrosalicylic acid (0.046 g, 0.2 mmol), pyridine (0.1 ml), NaOH (0.008 g, 0.2 mmol) and distilled water (10 ml) was put into a 20 ml Teflon-lined autoclave and then heated at 393 K for 48 h. Green block-like crystals of the title compound suitable for X-ray analysis were collected from the reaction mixture.

Structure description top

For related literature, see: He et al. (2005, 2006); Lemoine et al. (2004); Thurston et al. (2004); Valigura et al. (2004); Wang & Okabe (2004); Wen et al. (2007); Zhu et al. (2003).

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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Packing diagram of the title compound viewed down the c axis. Hydrogen bonds are denoted by dashed lines.

(2,2'-Bipyridine-κ²N,N')(3,5-dinitrosalicylato-κ²O¹,O²)(pyridine- κN)copper(II) top

Crystal data top

[Cu(C₇H₂N₂O₇)(C₅H₅N)(C₁₀H₈N₂)]	Z = 2
M_r = 524.93	F(000) = 534
Triclinic, P1	D_x = 1.654 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.981 (2) Å	Cell parameters from 3813 reflections
b = 10.269 (2) Å	θ = 1.9–25.5°
c = 11.913 (2) Å	µ = 1.10 mm⁻¹
α = 68.99 (3)°	T = 293 K
β = 67.88 (3)°	Block, green
γ = 79.08 (3)°	0.24 × 0.23 × 0.21 mm
V = 1053.9 (5) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3813 independent reflections
Radiation source: fine-focus sealed tube	3149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→11
T_min = 0.767, T_max = 0.797	k = −12→0
8700 measured reflections	l = −14→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0764P)² + 1.3696P] where P = (F_o² + 2F_c²)/3
3813 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Cu(C₇H₂N₂O₇)(C₅H₅N)(C₁₀H₈N₂)]	γ = 79.08 (3)°
M_r = 524.93	V = 1053.9 (5) Å³
Triclinic, P1	Z = 2
a = 9.981 (2) Å	Mo Kα radiation
b = 10.269 (2) Å	µ = 1.10 mm⁻¹
c = 11.913 (2) Å	T = 293 K
α = 68.99 (3)°	0.24 × 0.23 × 0.21 mm
β = 67.88 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3813 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3149 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.797	R_int = 0.052
8700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.10	Δρ_max = 0.38 e Å⁻³
3813 reflections	Δρ_min = −0.53 e Å⁻³
316 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.73644 (5)	0.53558 (5)	0.63796 (4)	0.03526 (19)
N1	1.1054 (5)	0.8518 (4)	0.4277 (5)	0.0568 (11)
N2	1.1139 (4)	0.8782 (4)	0.0098 (4)	0.0487 (10)
N3	0.5974 (4)	0.3880 (4)	0.7647 (3)	0.0398 (8)
N4	0.7636 (4)	0.5261 (4)	0.7993 (3)	0.0383 (8)
N5	0.5748 (4)	0.7234 (4)	0.6310 (3)	0.0392 (8)
O1	0.7897 (4)	0.4980 (4)	0.2997 (3)	0.0675 (12)
O2	0.7302 (3)	0.4896 (3)	0.4995 (3)	0.0474 (8)
O3	0.9040 (3)	0.6421 (3)	0.5376 (3)	0.0423 (7)
O4	1.0337 (5)	0.8415 (4)	0.5388 (4)	0.0742 (12)
O5	1.2219 (5)	0.9046 (5)	0.3731 (5)	0.0922 (15)
O6	1.2102 (4)	0.9586 (4)	−0.0363 (4)	0.0721 (12)
O7	1.0631 (4)	0.8460 (4)	−0.0548 (3)	0.0661 (10)
C1	0.9028 (4)	0.6550 (4)	0.3326 (4)	0.0316 (8)
C2	0.9467 (4)	0.6966 (4)	0.4161 (4)	0.0343 (9)
C3	1.0503 (4)	0.8015 (5)	0.3536 (4)	0.0398 (10)
C4	1.1040 (5)	0.8609 (5)	0.2222 (5)	0.0458 (11)
H4A	1.1713	0.9288	0.1848	0.055*
C5	1.0565 (5)	0.8179 (4)	0.1485 (4)	0.0398 (10)
C6	0.9573 (4)	0.7168 (4)	0.2024 (4)	0.0380 (9)
H6A	0.9267	0.6899	0.1498	0.046*
C7	0.8009 (5)	0.5402 (5)	0.3796 (4)	0.0383 (9)
C8	0.5166 (5)	0.3232 (5)	0.7363 (5)	0.0474 (11)
H8A	0.5211	0.3478	0.6519	0.057*
C9	0.4261 (6)	0.2202 (5)	0.8288 (5)	0.0589 (14)
H9A	0.3690	0.1776	0.8073	0.071*
C10	0.4227 (6)	0.1824 (5)	0.9525 (5)	0.0620 (15)
H10A	0.3635	0.1131	1.0158	0.074*
C11	0.5064 (6)	0.2467 (5)	0.9828 (5)	0.0554 (13)
H11A	0.5056	0.2204	1.0663	0.066*
C12	0.6925 (5)	0.4151 (6)	1.0246 (4)	0.0531 (12)
H12A	0.6369	0.3507	1.0977	0.064*
C13	0.7826 (6)	0.4939 (6)	1.0325 (5)	0.0614 (15)
H13A	0.7900	0.4832	1.1109	0.074*
C14	0.8622 (6)	0.5890 (6)	0.9233 (5)	0.0575 (13)
H14A	0.9236	0.6439	0.9271	0.069*
C15	0.8506 (5)	0.6029 (5)	0.8071 (5)	0.0480 (11)
H15A	0.9049	0.6673	0.7332	0.058*
C16	0.6849 (5)	0.4322 (5)	0.9066 (4)	0.0404 (10)
C17	0.5929 (5)	0.3521 (4)	0.8872 (4)	0.0412 (10)
C18	0.5984 (5)	0.8385 (5)	0.6463 (4)	0.0448 (11)
H18A	0.6903	0.8471	0.6448	0.054*
C19	0.4958 (6)	0.9440 (5)	0.6640 (5)	0.0536 (12)
H19A	0.5174	1.0221	0.6747	0.064*
C20	0.3603 (6)	0.9338 (6)	0.6658 (5)	0.0596 (14)
H20A	0.2879	1.0038	0.6796	0.072*
C21	0.3327 (5)	0.8176 (6)	0.6469 (5)	0.0575 (14)
H21A	0.2421	0.8083	0.6463	0.069*
C22	0.4424 (5)	0.7168 (5)	0.6292 (4)	0.0468 (11)
H22A	0.4245	0.6394	0.6151	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0393 (3)	0.0428 (3)	0.0239 (3)	−0.0148 (2)	−0.0062 (2)	−0.0092 (2)
N1	0.054 (3)	0.053 (3)	0.074 (3)	−0.022 (2)	−0.024 (2)	−0.020 (2)
N2	0.045 (2)	0.041 (2)	0.036 (2)	0.0020 (17)	−0.0007 (18)	0.0001 (17)
N3	0.046 (2)	0.0372 (19)	0.0293 (17)	−0.0084 (16)	−0.0018 (15)	−0.0104 (15)
N4	0.0372 (18)	0.049 (2)	0.0327 (17)	−0.0015 (15)	−0.0127 (15)	−0.0175 (16)
N5	0.044 (2)	0.042 (2)	0.0341 (18)	−0.0130 (16)	−0.0160 (16)	−0.0069 (15)
O1	0.086 (3)	0.095 (3)	0.0326 (17)	−0.057 (2)	−0.0099 (17)	−0.0172 (17)
O2	0.0548 (19)	0.063 (2)	0.0282 (14)	−0.0365 (16)	−0.0002 (14)	−0.0169 (14)
O3	0.0400 (16)	0.0597 (19)	0.0293 (14)	−0.0219 (14)	−0.0053 (12)	−0.0140 (13)
O4	0.098 (3)	0.084 (3)	0.058 (2)	−0.044 (2)	−0.024 (2)	−0.025 (2)
O5	0.067 (3)	0.121 (4)	0.105 (3)	−0.055 (3)	−0.013 (3)	−0.046 (3)
O6	0.064 (2)	0.062 (2)	0.053 (2)	−0.0251 (19)	0.0093 (19)	0.0038 (18)
O7	0.071 (2)	0.074 (3)	0.0321 (17)	−0.006 (2)	−0.0065 (17)	−0.0024 (17)
C1	0.0288 (19)	0.037 (2)	0.0275 (18)	−0.0069 (16)	−0.0070 (16)	−0.0091 (16)
C2	0.0273 (19)	0.038 (2)	0.037 (2)	−0.0056 (16)	−0.0066 (16)	−0.0129 (17)
C3	0.035 (2)	0.041 (2)	0.049 (2)	−0.0097 (18)	−0.0141 (19)	−0.0166 (19)
C4	0.034 (2)	0.036 (2)	0.052 (3)	−0.0099 (18)	−0.003 (2)	−0.004 (2)
C5	0.035 (2)	0.034 (2)	0.034 (2)	−0.0043 (17)	−0.0023 (17)	−0.0015 (17)
C6	0.038 (2)	0.043 (2)	0.0294 (19)	−0.0043 (18)	−0.0105 (17)	−0.0073 (17)
C7	0.040 (2)	0.051 (3)	0.0290 (19)	−0.0168 (19)	−0.0113 (18)	−0.0123 (18)
C8	0.051 (3)	0.044 (3)	0.044 (2)	−0.018 (2)	−0.003 (2)	−0.015 (2)
C9	0.058 (3)	0.048 (3)	0.064 (3)	−0.017 (2)	−0.001 (3)	−0.024 (2)
C10	0.062 (3)	0.044 (3)	0.057 (3)	−0.020 (2)	0.003 (3)	−0.006 (2)
C11	0.061 (3)	0.045 (3)	0.035 (2)	−0.001 (2)	−0.003 (2)	0.001 (2)
C12	0.052 (3)	0.069 (3)	0.030 (2)	0.011 (2)	−0.014 (2)	−0.014 (2)
C13	0.065 (3)	0.089 (4)	0.034 (2)	0.020 (3)	−0.025 (2)	−0.027 (3)
C14	0.051 (3)	0.084 (4)	0.057 (3)	0.009 (3)	−0.030 (3)	−0.038 (3)
C15	0.047 (3)	0.062 (3)	0.042 (2)	0.001 (2)	−0.020 (2)	−0.021 (2)
C16	0.039 (2)	0.045 (2)	0.028 (2)	0.0075 (19)	−0.0083 (18)	−0.0098 (18)
C17	0.042 (2)	0.036 (2)	0.031 (2)	0.0048 (18)	−0.0031 (18)	−0.0070 (17)
C18	0.048 (3)	0.047 (3)	0.042 (2)	−0.019 (2)	−0.013 (2)	−0.011 (2)
C19	0.066 (3)	0.046 (3)	0.048 (3)	−0.007 (2)	−0.012 (2)	−0.020 (2)
C20	0.058 (3)	0.063 (3)	0.042 (3)	0.005 (3)	−0.011 (2)	−0.010 (2)
C21	0.040 (3)	0.077 (4)	0.047 (3)	−0.016 (3)	−0.016 (2)	−0.002 (3)
C22	0.048 (3)	0.052 (3)	0.043 (2)	−0.016 (2)	−0.018 (2)	−0.009 (2)

Geometric parameters (Å, º) top

Cu1—O2	1.896 (3)	C6—H6A	0.9300
Cu1—O3	1.917 (3)	C8—C9	1.388 (6)
Cu1—N4	2.007 (3)	C8—H8A	0.9300
Cu1—N3	2.020 (3)	C9—C10	1.372 (8)
Cu1—N5	2.267 (4)	C9—H9A	0.9300
N1—O5	1.220 (5)	C10—C11	1.367 (8)
N1—O4	1.220 (6)	C10—H10A	0.9300
N1—C3	1.466 (6)	C11—C17	1.394 (6)
N2—O6	1.219 (5)	C11—H11A	0.9300
N2—O7	1.224 (6)	C12—C13	1.367 (8)
N2—C5	1.460 (5)	C12—C16	1.382 (6)
N3—C8	1.334 (6)	C12—H12A	0.9300
N3—C17	1.356 (6)	C13—C14	1.372 (8)
N4—C15	1.326 (6)	C13—H13A	0.9300
N4—C16	1.352 (6)	C14—C15	1.386 (6)
N5—C18	1.334 (6)	C14—H14A	0.9300
N5—C22	1.344 (6)	C15—H15A	0.9300
O1—C7	1.225 (5)	C16—C17	1.468 (6)
O2—C7	1.287 (5)	C18—C19	1.360 (7)
O3—C2	1.278 (5)	C18—H18A	0.9300
C1—C6	1.376 (5)	C19—C20	1.367 (8)
C1—C2	1.439 (6)	C19—H19A	0.9300
C1—C7	1.513 (5)	C20—C21	1.384 (8)
C2—C3	1.432 (5)	C20—H20A	0.9300
C3—C4	1.385 (6)	C21—C22	1.366 (7)
C4—C5	1.364 (7)	C21—H21A	0.9300
C4—H4A	0.9300	C22—H22A	0.9300
C5—C6	1.379 (6)

O2—Cu1—O3	94.21 (12)	O2—C7—C1	120.4 (3)
O2—Cu1—N4	163.41 (15)	N3—C8—C9	122.0 (5)
O3—Cu1—N4	90.62 (14)	N3—C8—H8A	119.0
O2—Cu1—N3	91.20 (13)	C9—C8—H8A	119.0
O3—Cu1—N3	164.71 (15)	C10—C9—C8	118.6 (5)
N4—Cu1—N3	80.41 (15)	C10—C9—H9A	120.7
O2—Cu1—N5	99.04 (15)	C8—C9—H9A	120.7
O3—Cu1—N5	95.26 (13)	C11—C10—C9	120.1 (5)
N4—Cu1—N5	96.30 (14)	C11—C10—H10A	120.0
N3—Cu1—N5	98.00 (14)	C9—C10—H10A	120.0
O5—N1—O4	123.0 (5)	C10—C11—C17	119.3 (5)
O5—N1—C3	117.2 (5)	C10—C11—H11A	120.3
O4—N1—C3	119.7 (4)	C17—C11—H11A	120.3
O6—N2—O7	123.1 (4)	C13—C12—C16	119.1 (5)
O6—N2—C5	118.3 (5)	C13—C12—H12A	120.4
O7—N2—C5	118.6 (4)	C16—C12—H12A	120.4
C8—N3—C17	119.5 (4)	C12—C13—C14	119.2 (5)
C8—N3—Cu1	125.5 (3)	C12—C13—H13A	120.4
C17—N3—Cu1	114.9 (3)	C14—C13—H13A	120.4
C15—N4—C16	119.4 (4)	C13—C14—C15	119.6 (5)
C15—N4—Cu1	125.4 (3)	C13—C14—H14A	120.2
C16—N4—Cu1	115.2 (3)	C15—C14—H14A	120.2
C18—N5—C22	116.5 (4)	N4—C15—C14	121.3 (5)
C18—N5—Cu1	121.6 (3)	N4—C15—H15A	119.4
C22—N5—Cu1	121.3 (3)	C14—C15—H15A	119.4
C7—O2—Cu1	128.7 (3)	N4—C16—C12	121.4 (4)
C2—O3—Cu1	125.1 (3)	N4—C16—C17	115.0 (4)
C6—C1—C2	120.3 (4)	C12—C16—C17	123.6 (4)
C6—C1—C7	116.3 (4)	N3—C17—C11	120.5 (5)
C2—C1—C7	123.3 (3)	N3—C17—C16	114.4 (4)
O3—C2—C3	120.5 (4)	C11—C17—C16	125.1 (4)
O3—C2—C1	124.2 (4)	N5—C18—C19	123.6 (4)
C3—C2—C1	115.3 (4)	N5—C18—H18A	118.2
C4—C3—C2	123.0 (4)	C19—C18—H18A	118.2
C4—C3—N1	116.3 (4)	C18—C19—C20	119.1 (5)
C2—C3—N1	120.7 (4)	C18—C19—H19A	120.5
C5—C4—C3	118.7 (4)	C20—C19—H19A	120.5
C5—C4—H4A	120.6	C19—C20—C21	118.9 (5)
C3—C4—H4A	120.6	C19—C20—H20A	120.5
C4—C5—C6	121.3 (4)	C21—C20—H20A	120.5
C4—C5—N2	119.3 (4)	C22—C21—C20	118.1 (5)
C6—C5—N2	119.4 (4)	C22—C21—H21A	121.0
C1—C6—C5	121.3 (4)	C20—C21—H21A	121.0
C1—C6—H6A	119.3	N5—C22—C21	123.7 (5)
C5—C6—H6A	119.3	N5—C22—H22A	118.2
O1—C7—O2	122.1 (4)	C21—C22—H22A	118.2
O1—C7—C1	117.5 (4)

O2—Cu1—N3—C8	−14.4 (4)	C3—C4—C5—N2	−179.1 (4)
O3—Cu1—N3—C8	−125.2 (5)	O6—N2—C5—C4	4.9 (6)
N4—Cu1—N3—C8	−180.0 (4)	O7—N2—C5—C4	−175.0 (4)
N5—Cu1—N3—C8	84.9 (4)	O6—N2—C5—C6	−173.9 (4)
O2—Cu1—N3—C17	163.5 (3)	O7—N2—C5—C6	6.1 (6)
O3—Cu1—N3—C17	52.7 (6)	C2—C1—C6—C5	1.1 (6)
N4—Cu1—N3—C17	−2.2 (3)	C7—C1—C6—C5	−176.9 (4)
N5—Cu1—N3—C17	−97.2 (3)	C4—C5—C6—C1	−0.2 (7)
O2—Cu1—N4—C15	120.4 (5)	N2—C5—C6—C1	178.6 (4)
O3—Cu1—N4—C15	13.3 (4)	Cu1—O2—C7—O1	177.8 (4)
N3—Cu1—N4—C15	−179.1 (4)	Cu1—O2—C7—C1	−1.7 (7)
N5—Cu1—N4—C15	−82.1 (4)	C6—C1—C7—O1	9.6 (6)
O2—Cu1—N4—C16	−59.5 (6)	C2—C1—C7—O1	−168.3 (4)
O3—Cu1—N4—C16	−166.6 (3)	C6—C1—C7—O2	−170.8 (4)
N3—Cu1—N4—C16	1.0 (3)	C2—C1—C7—O2	11.3 (7)
N5—Cu1—N4—C16	98.0 (3)	C17—N3—C8—C9	0.6 (7)
O2—Cu1—N5—C18	−138.0 (3)	Cu1—N3—C8—C9	178.4 (4)
O3—Cu1—N5—C18	−42.9 (3)	N3—C8—C9—C10	−1.4 (8)
N4—Cu1—N5—C18	48.4 (3)	C8—C9—C10—C11	0.5 (8)
N3—Cu1—N5—C18	129.5 (3)	C9—C10—C11—C17	1.0 (8)
O2—Cu1—N5—C22	51.4 (3)	C16—C12—C13—C14	0.7 (8)
O3—Cu1—N5—C22	146.5 (3)	C12—C13—C14—C15	−0.4 (8)
N4—Cu1—N5—C22	−122.3 (3)	C16—N4—C15—C14	−0.2 (7)
N3—Cu1—N5—C22	−41.1 (3)	Cu1—N4—C15—C14	180.0 (4)
O3—Cu1—O2—C7	−11.4 (4)	C13—C14—C15—N4	0.2 (8)
N4—Cu1—O2—C7	−118.0 (5)	C15—N4—C16—C12	0.4 (6)
N3—Cu1—O2—C7	−177.1 (4)	Cu1—N4—C16—C12	−179.7 (3)
N5—Cu1—O2—C7	84.6 (4)	C15—N4—C16—C17	−179.6 (4)
O2—Cu1—O3—C2	21.7 (4)	Cu1—N4—C16—C17	0.3 (5)
N4—Cu1—O3—C2	−174.2 (4)	C13—C12—C16—N4	−0.6 (7)
N3—Cu1—O3—C2	132.1 (5)	C13—C12—C16—C17	179.3 (4)
N5—Cu1—O3—C2	−77.8 (4)	C8—N3—C17—C11	1.0 (6)
Cu1—O3—C2—C3	164.5 (3)	Cu1—N3—C17—C11	−177.0 (3)
Cu1—O3—C2—C1	−18.7 (6)	C8—N3—C17—C16	−179.1 (4)
C6—C1—C2—O3	−178.2 (4)	Cu1—N3—C17—C16	2.9 (5)
C7—C1—C2—O3	−0.4 (7)	C10—C11—C17—N3	−1.8 (7)
C6—C1—C2—C3	−1.3 (6)	C10—C11—C17—C16	178.3 (4)
C7—C1—C2—C3	176.5 (4)	N4—C16—C17—N3	−2.1 (5)
O3—C2—C3—C4	177.8 (4)	C12—C16—C17—N3	177.9 (4)
C1—C2—C3—C4	0.7 (6)	N4—C16—C17—C11	177.7 (4)
O3—C2—C3—N1	−2.1 (7)	C12—C16—C17—C11	−2.2 (7)
C1—C2—C3—N1	−179.2 (4)	C22—N5—C18—C19	2.3 (7)
O5—N1—C3—C4	−22.6 (7)	Cu1—N5—C18—C19	−168.7 (4)
O4—N1—C3—C4	156.2 (5)	N5—C18—C19—C20	−0.4 (8)
O5—N1—C3—C2	157.3 (5)	C18—C19—C20—C21	−1.4 (8)
O4—N1—C3—C2	−23.8 (7)	C19—C20—C21—C22	1.0 (7)
C2—C3—C4—C5	0.0 (7)	C18—N5—C22—C21	−2.7 (7)
N1—C3—C4—C5	180.0 (4)	Cu1—N5—C22—C21	168.4 (4)
C3—C4—C5—C6	−0.3 (7)	C20—C21—C22—N5	1.0 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.31	3.226 (6)	169
C22—H22A···O1ⁱⁱ	0.93	2.47	3.174 (6)	133
C9—H9A···O6ⁱⁱⁱ	0.93	2.68	3.306 (6)	125
C19—H19A···O5^iv	0.93	2.64	3.283 (6)	126

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₂N₂O₇)(C₅H₅N)(C₁₀H₈N₂)]
M_r	524.93
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.981 (2), 10.269 (2), 11.913 (2)
α, β, γ (°)	68.99 (3), 67.88 (3), 79.08 (3)
V (Å³)	1053.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.24 × 0.23 × 0.21

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.767, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	8700, 3813, 3149
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.149, 1.10
No. of reflections	3813
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.53

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

Selected geometric parameters (Å, º) top

Cu1—O2	1.896 (3)	Cu1—N3	2.020 (3)
Cu1—O3	1.917 (3)	Cu1—N5	2.267 (4)
Cu1—N4	2.007 (3)

O2—Cu1—O3	94.21 (12)	N4—Cu1—N3	80.41 (15)
O2—Cu1—N4	163.41 (15)	O2—Cu1—N5	99.04 (15)
O3—Cu1—N4	90.62 (14)	O3—Cu1—N5	95.26 (13)
O2—Cu1—N3	91.20 (13)	N4—Cu1—N5	96.30 (14)
O3—Cu1—N3	164.71 (15)	N3—Cu1—N5	98.00 (14)