Poly[[(μ3-2,4,6-tri-4-pyridyl-1,3,5-triazine)copper(I)] nitrate monohydrate]

Feng, M.; Tian, H.-J.; Mi, H.-F.; Hu, T.-L.

doi:10.1107/S1600536811011445

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m515

doi:10.1107/S1600536811011445

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Poly[[(μ₃-2,4,6-tri-4-pyridyl-1,3,5-triazine)copper(I)] nitrate monohydrate]

Miao Feng,^a Hui-Juan Tian,^b Huai-Feng Mi ^a ^* and Tong-Liang Hu ^b

^aBiochemical Section of Key Laboratory of Functional Polymer Materials, Ministry of Education of China, Chemical School of Nankai University, 300071 Tianjin, People's Republic of China, and ^bDepartment of Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: changlianze@gmail.com

(Received 19 March 2011; accepted 28 March 2011; online 31 March 2011)

In the title compound, {[Cu(C₁₈H₁₂N₆)]NO₃·H₂O}_n, the Cu^I ion is coordinated by three N atoms [Cu—N 1.962 (3)–2.019 (3) Å] from three 2,4,6-tri-4-pyridyl-1,3,5-triazine (L) ligands. Each L ligand bridges three Cu^I atoms, generating a positively charged three-dimensional polymeric network with voids propagated along the b axis. These voids are filled with NO₃⁻ anions with a shortest Cu⋯O distance of 2.645 (3) Å and water molecules, which are linked into negatively charged helical chains via intermolecular O—H⋯O hydrogen bonds.

Related literature

For metal complexes with 2,4,6-tri(4-pyridyl)-1,3,5-triazine ligands, see: Abrahams et al. (1999 ); Dybtsev et al. (2004 ); Barrios et al. (2007 ).

Experimental

Crystal data

[Cu(C₁₈H₁₂N₆)]NO₃·H₂O
M_r = 455.90
Monoclinic, P 2₁ /c
a = 9.917 (2) Å
b = 8.7409 (17) Å
c = 22.499 (6) Å
β = 107.43 (3)°
V = 1860.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.10 mm

Data collection

Rigaku SCX-mini diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.736, T_max = 1.000
18394 measured reflections
4262 independent reflections
2717 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.125
S = 1.09
4262 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4W—H4WA⋯O2	0.91	2.23	3.057 (7)	151
O4W—H4WB⋯O2ⁱ	0.92	2.23	3.082 (7)	155
Symmetry code: (i) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011445/cv5064sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011445/cv5064Isup2.hkl

checkCIF report

Comment top

As an interesting polydentate nitrogen donor ligand, 2,4,6-tris(4-pyridyl)-1,3,5-triazine(L) has attracted increasing attention in the synthesis of novel transition metal complexes with novel topology and properties (Abrahams et al. 1999; Dybtsev et al. 2004; Barrios et al. 2007). Our interest in 2,4,6-tris(4-pyridyl)-1,3,5-triazine transition metal complexes prompts us to report here the crystal structure of the title compound (1).

In 1 (Fig. 1), each Cu^I ion is coordinated by three N atoms [Cu—N 1.962 (3)–2.019 (3) Å] from three ligands L, and each ligand L bridge three Cu^I centers generating positively charged three-dimensional polymeric network with the voids propagated along axis b. These voids are filled with NO₃^- anions with the shortest Cu···O distance of 2.645 (3) Å and crystalline water molecules, which are linked into negatively charged helical chains via intermolecular O—H···O hydrogen bonds.

Related literature top

For metal complexes with 2,4,6-tris(4-pyridyl)-1,3,5-triazine ligands, see: Abrahams et al. (1999); Dybtsev et al. (2004); Barrios et al. (2007).

Experimental top

In a typical synthesis, a mixture of Cu(NO₃)₂.6H₂O (1 mmol), 2,4,6-tris(4-pyridyl)-1,3,5-triazine (1 mmol) and methanol (10 ml), was added to a 20 ml Teflon-lined reactor under autogenous pressure at 140 °C for 3 days.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: publCIF (Westrip, 2010).

Figures top

Fig. 1. A content of the asymmetric unit of 1 showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level. The O—H···O hydrogen bond is shown by the dashed green line, and the shortest Cu···O distance is shown by the dotted red line.

Poly[[(µ₃-2,4,6-tri-4-pyridyl-1,3,5-triazine)copper(I)] nitrate monohydrate] top

Crystal data top

[Cu(C₁₈H₁₂N₆)]NO₃·H₂O	F(000) = 928
M_r = 455.90	D_x = 1.627 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14882 reflections
a = 9.917 (2) Å	θ = 3.0–27.7°
b = 8.7409 (17) Å	µ = 1.22 mm⁻¹
c = 22.499 (6) Å	T = 293 K
β = 107.43 (3)°	Block, red
V = 1860.7 (7) Å³	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection top

Rigaku SCX-mini diffractometer	4262 independent reflections
Radiation source: fine-focus sealed tube	2717 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.736, T_max = 1.000	k = −11→11
18394 measured reflections	l = −28→29

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0335P)² + 2.1056P] where P = (F_o² + 2F_c²)/3
4262 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Cu(C₁₈H₁₂N₆)]NO₃·H₂O	V = 1860.7 (7) Å³
M_r = 455.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.917 (2) Å	µ = 1.22 mm⁻¹
b = 8.7409 (17) Å	T = 293 K
c = 22.499 (6) Å	0.10 × 0.10 × 0.10 mm
β = 107.43 (3)°

Data collection top

Rigaku SCX-mini diffractometer	4262 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2717 reflections with I > 2σ(I)
T_min = 0.736, T_max = 1.000	R_int = 0.097
18394 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.09	Δρ_max = 0.36 e Å⁻³
4262 reflections	Δρ_min = −0.35 e Å⁻³
271 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	−0.1691 (5)	0.5154 (5)	0.27731 (19)	0.0411 (12)
H1	−0.2584	0.5537	0.2569	0.049*
C2	−0.1040 (4)	0.5629 (5)	0.33689 (19)	0.0380 (11)
H2	−0.1487	0.6318	0.3563	0.046*
C3	0.0293 (4)	0.5073 (5)	0.36812 (18)	0.0296 (9)
C4	0.0904 (4)	0.4047 (5)	0.33735 (18)	0.0344 (10)
H4	0.1795	0.3642	0.3568	0.041*
C5	0.0177 (4)	0.3635 (5)	0.27772 (19)	0.0383 (11)
H5	0.0600	0.2945	0.2573	0.046*
C6	0.5691 (4)	0.2273 (5)	0.55716 (19)	0.0379 (11)
H6	0.5981	0.1474	0.5366	0.046*
C7	0.4531 (4)	0.3104 (5)	0.52532 (18)	0.0321 (10)
H7	0.4053	0.2872	0.4840	0.039*
C8	0.4077 (4)	0.4293 (5)	0.55511 (18)	0.0276 (9)
C9	0.4827 (4)	0.4592 (5)	0.61641 (19)	0.0398 (11)
H9	0.4557	0.5381	0.6382	0.048*
C10	0.5983 (4)	0.3696 (5)	0.64455 (19)	0.0407 (11)
H10	0.6482	0.3904	0.6858	0.049*
C11	0.0496 (4)	0.9682 (5)	0.6342 (2)	0.0388 (11)
H11	0.0994	1.0111	0.6722	0.047*
C12	0.1191 (4)	0.8664 (5)	0.60714 (18)	0.0354 (10)
H12	0.2124	0.8393	0.6271	0.042*
C13	0.0474 (4)	0.8050 (5)	0.54967 (17)	0.0270 (9)
C14	−0.0906 (4)	0.8507 (5)	0.52211 (18)	0.0310 (10)
H14	−0.1408	0.8143	0.4829	0.037*
C15	−0.1526 (4)	0.9498 (5)	0.55297 (19)	0.0360 (10)
H15	−0.2462	0.9775	0.5342	0.043*
C16	0.1021 (4)	0.5523 (5)	0.43321 (17)	0.0281 (9)
C17	0.2806 (4)	0.5165 (5)	0.52141 (18)	0.0276 (9)
C18	0.1122 (4)	0.6898 (5)	0.51893 (18)	0.0278 (9)
Cu1	−0.19856 (5)	0.38069 (7)	0.15691 (2)	0.03757 (18)
N1	−0.1108 (4)	0.4169 (4)	0.24703 (15)	0.0364 (9)
N2	0.6432 (3)	0.2554 (4)	0.61653 (15)	0.0321 (8)
N3	−0.0852 (3)	1.0091 (4)	0.60904 (15)	0.0329 (8)
N4	0.0422 (3)	0.6577 (4)	0.45964 (15)	0.0313 (8)
N5	0.2221 (3)	0.4792 (4)	0.46175 (14)	0.0290 (8)
N6	0.2306 (3)	0.6215 (4)	0.55228 (14)	0.0308 (8)
N7	−0.4795 (5)	0.6084 (6)	0.1312 (2)	0.0619 (12)
O1	−0.3565 (4)	0.6301 (5)	0.13251 (19)	0.0806 (12)
O2	−0.5122 (4)	0.6217 (6)	0.18018 (19)	0.1031 (17)
O3	−0.5691 (4)	0.5721 (6)	0.0832 (2)	0.0948 (15)
O4W	−0.3407 (5)	0.8630 (5)	0.2697 (2)	0.1142 (17)
H4WA	−0.4160	0.8171	0.2417	0.142*
H4WB	−0.3653	0.9580	0.2804	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.033 (2)	0.058 (3)	0.026 (2)	0.007 (2)	−0.002 (2)	0.001 (2)
C2	0.031 (2)	0.047 (3)	0.034 (2)	0.010 (2)	0.006 (2)	−0.007 (2)
C3	0.029 (2)	0.033 (2)	0.024 (2)	−0.0004 (19)	0.0058 (18)	0.0032 (18)
C4	0.030 (2)	0.041 (3)	0.029 (2)	0.008 (2)	0.0042 (19)	−0.002 (2)
C5	0.043 (3)	0.041 (3)	0.031 (2)	0.005 (2)	0.011 (2)	−0.005 (2)
C6	0.036 (2)	0.040 (3)	0.033 (2)	0.014 (2)	0.005 (2)	−0.006 (2)
C7	0.033 (2)	0.035 (3)	0.023 (2)	0.0064 (19)	0.0021 (19)	−0.0029 (18)
C8	0.022 (2)	0.031 (2)	0.027 (2)	0.0049 (17)	0.0033 (17)	0.0016 (18)
C9	0.040 (3)	0.041 (3)	0.034 (2)	0.015 (2)	0.005 (2)	−0.007 (2)
C10	0.040 (3)	0.047 (3)	0.028 (2)	0.011 (2)	−0.001 (2)	−0.005 (2)
C11	0.035 (2)	0.045 (3)	0.034 (2)	0.002 (2)	0.006 (2)	−0.010 (2)
C12	0.026 (2)	0.042 (3)	0.035 (2)	0.006 (2)	0.0054 (19)	−0.002 (2)
C13	0.026 (2)	0.027 (2)	0.028 (2)	0.0003 (17)	0.0086 (18)	0.0022 (18)
C14	0.029 (2)	0.032 (3)	0.029 (2)	0.0042 (19)	0.0052 (18)	−0.0044 (19)
C15	0.029 (2)	0.043 (3)	0.032 (2)	0.003 (2)	0.001 (2)	−0.001 (2)
C16	0.027 (2)	0.029 (2)	0.026 (2)	0.0028 (18)	0.0038 (18)	0.0024 (18)
C17	0.026 (2)	0.028 (2)	0.027 (2)	−0.0003 (18)	0.0060 (18)	0.0015 (18)
C18	0.024 (2)	0.028 (2)	0.029 (2)	0.0002 (17)	0.0048 (18)	0.0023 (18)
Cu1	0.0337 (3)	0.0470 (4)	0.0281 (3)	−0.0141 (3)	0.0034 (2)	−0.0025 (3)
N1	0.037 (2)	0.044 (2)	0.0250 (18)	−0.0085 (17)	0.0054 (16)	0.0013 (16)
N2	0.0297 (19)	0.035 (2)	0.0277 (18)	0.0108 (16)	0.0024 (16)	0.0016 (16)
N3	0.0270 (19)	0.037 (2)	0.034 (2)	0.0079 (16)	0.0077 (16)	−0.0036 (17)
N4	0.0312 (19)	0.032 (2)	0.0281 (18)	0.0071 (15)	0.0048 (16)	0.0006 (15)
N5	0.0273 (18)	0.032 (2)	0.0249 (18)	0.0054 (15)	0.0038 (15)	−0.0011 (15)
N6	0.0275 (17)	0.032 (2)	0.0303 (18)	0.0049 (17)	0.0052 (15)	−0.0014 (17)
N7	0.044 (3)	0.080 (4)	0.058 (3)	0.017 (3)	0.010 (2)	0.012 (3)
O1	0.054 (2)	0.097 (3)	0.097 (3)	−0.008 (2)	0.032 (2)	0.008 (3)
O2	0.064 (3)	0.190 (5)	0.060 (3)	−0.006 (3)	0.025 (2)	0.000 (3)
O3	0.068 (3)	0.131 (4)	0.071 (3)	0.022 (3)	−0.002 (2)	−0.021 (3)
O4W	0.088 (3)	0.100 (4)	0.130 (4)	0.007 (3)	−0.005 (3)	−0.021 (3)

Geometric parameters (Å, º) top

C1—N1	1.332 (5)	C12—C13	1.384 (5)
C1—C2	1.367 (5)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.381 (5)
C2—C3	1.386 (5)	C13—C18	1.473 (5)
C2—H2	0.9300	C14—C15	1.366 (5)
C3—C4	1.380 (5)	C14—H14	0.9300
C3—C16	1.479 (5)	C15—N3	1.342 (5)
C4—C5	1.367 (5)	C15—H15	0.9300
C4—H4	0.9300	C16—N4	1.329 (5)
C5—N1	1.338 (5)	C16—N5	1.334 (5)
C5—H5	0.9300	C17—N6	1.332 (5)
C6—N2	1.340 (5)	C17—N5	1.334 (5)
C6—C7	1.368 (5)	C18—N6	1.331 (5)
C6—H6	0.9300	C18—N4	1.336 (5)
C7—C8	1.383 (5)	Cu1—N2ⁱ	1.962 (3)
C7—H7	0.9300	Cu1—N1	1.978 (3)
C8—C9	1.382 (5)	Cu1—N3ⁱⁱ	2.019 (3)
C8—C17	1.474 (5)	N2—Cu1ⁱⁱⁱ	1.962 (3)
C9—C10	1.376 (5)	N3—Cu1^iv	2.019 (3)
C9—H9	0.9300	N7—O3	1.218 (5)
C10—N2	1.326 (5)	N7—O1	1.226 (5)
C10—H10	0.9300	N7—O2	1.243 (5)
C11—N3	1.335 (5)	O4W—H4WA	0.9125
C11—C12	1.374 (6)	O4W—H4WB	0.9175
C11—H11	0.9300

N1—C1—C2	123.3 (4)	C14—C13—C18	120.0 (3)
N1—C1—H1	118.4	C12—C13—C18	122.0 (3)
C2—C1—H1	118.4	C15—C14—C13	119.4 (4)
C1—C2—C3	119.3 (4)	C15—C14—H14	120.3
C1—C2—H2	120.4	C13—C14—H14	120.3
C3—C2—H2	120.4	N3—C15—C14	123.3 (4)
C4—C3—C2	118.0 (4)	N3—C15—H15	118.3
C4—C3—C16	120.8 (3)	C14—C15—H15	118.3
C2—C3—C16	121.2 (4)	N4—C16—N5	124.8 (3)
C5—C4—C3	118.8 (4)	N4—C16—C3	118.4 (3)
C5—C4—H4	120.6	N5—C16—C3	116.7 (4)
C3—C4—H4	120.6	N6—C17—N5	125.1 (3)
N1—C5—C4	123.7 (4)	N6—C17—C8	118.8 (3)
N1—C5—H5	118.1	N5—C17—C8	116.0 (4)
C4—C5—H5	118.1	N6—C18—N4	125.1 (4)
N2—C6—C7	123.3 (4)	N6—C18—C13	118.5 (3)
N2—C6—H6	118.4	N4—C18—C13	116.3 (3)
C7—C6—H6	118.4	N2ⁱ—Cu1—N1	128.12 (14)
C6—C7—C8	119.4 (4)	N2ⁱ—Cu1—N3ⁱⁱ	122.55 (14)
C6—C7—H7	120.3	N1—Cu1—N3ⁱⁱ	109.03 (14)
C8—C7—H7	120.3	C1—N1—C5	116.9 (3)
C9—C8—C7	118.0 (4)	C1—N1—Cu1	120.2 (3)
C9—C8—C17	122.5 (4)	C5—N1—Cu1	122.1 (3)
C7—C8—C17	119.5 (3)	C10—N2—C6	116.7 (3)
C10—C9—C8	118.5 (4)	C10—N2—Cu1ⁱⁱⁱ	124.9 (3)
C10—C9—H9	120.8	C6—N2—Cu1ⁱⁱⁱ	118.3 (3)
C8—C9—H9	120.8	C11—N3—C15	116.6 (4)
N2—C10—C9	124.2 (4)	C11—N3—Cu1^iv	123.3 (3)
N2—C10—H10	117.9	C15—N3—Cu1^iv	119.1 (3)
C9—C10—H10	117.9	C16—N4—C18	115.1 (3)
N3—C11—C12	123.9 (4)	C17—N5—C16	115.1 (3)
N3—C11—H11	118.1	C18—N6—C17	114.7 (3)
C12—C11—H11	118.1	O3—N7—O1	121.1 (5)
C11—C12—C13	118.6 (4)	O3—N7—O2	119.7 (5)
C11—C12—H12	120.7	O1—N7—O2	119.1 (5)
C13—C12—H12	120.7	H4WA—O4W—H4WB	110.6
C14—C13—C12	118.0 (4)

N1—C1—C2—C3	0.1 (7)	C12—C13—C18—N4	−169.4 (4)
C1—C2—C3—C4	−0.4 (6)	C2—C1—N1—C5	0.2 (7)
C1—C2—C3—C16	−178.4 (4)	C2—C1—N1—Cu1	−170.1 (3)
C2—C3—C4—C5	0.4 (6)	C4—C5—N1—C1	−0.1 (6)
C16—C3—C4—C5	178.4 (4)	C4—C5—N1—Cu1	169.9 (3)
C3—C4—C5—N1	−0.2 (7)	N2ⁱ—Cu1—N1—C1	−82.3 (4)
N2—C6—C7—C8	−0.4 (7)	N3ⁱⁱ—Cu1—N1—C1	103.9 (3)
C6—C7—C8—C9	0.2 (6)	N2ⁱ—Cu1—N1—C5	107.9 (3)
C6—C7—C8—C17	−178.5 (4)	N3ⁱⁱ—Cu1—N1—C5	−65.8 (4)
C7—C8—C9—C10	0.0 (6)	C9—C10—N2—C6	−0.3 (7)
C17—C8—C9—C10	178.6 (4)	C9—C10—N2—Cu1ⁱⁱⁱ	−176.6 (4)
C8—C9—C10—N2	0.1 (7)	C7—C6—N2—C10	0.5 (7)
N3—C11—C12—C13	1.8 (7)	C7—C6—N2—Cu1ⁱⁱⁱ	177.0 (3)
C11—C12—C13—C14	0.6 (6)	C12—C11—N3—C15	−2.5 (7)
C11—C12—C13—C18	−177.1 (4)	C12—C11—N3—Cu1^iv	165.7 (3)
C12—C13—C14—C15	−2.2 (6)	C14—C15—N3—C11	0.8 (6)
C18—C13—C14—C15	175.6 (4)	C14—C15—N3—Cu1^iv	−167.9 (3)
C13—C14—C15—N3	1.5 (7)	N5—C16—N4—C18	0.7 (6)
C4—C3—C16—N4	176.4 (4)	C3—C16—N4—C18	178.4 (3)
C2—C3—C16—N4	−5.6 (6)	N6—C18—N4—C16	−2.4 (6)
C4—C3—C16—N5	−5.7 (6)	C13—C18—N4—C16	−179.3 (3)
C2—C3—C16—N5	172.2 (4)	N6—C17—N5—C16	−2.1 (6)
C9—C8—C17—N6	−4.5 (6)	C8—C17—N5—C16	175.8 (3)
C7—C8—C17—N6	174.0 (4)	N4—C16—N5—C17	1.3 (6)
C9—C8—C17—N5	177.5 (4)	C3—C16—N5—C17	−176.4 (3)
C7—C8—C17—N5	−4.0 (6)	N4—C18—N6—C17	1.7 (6)
C14—C13—C18—N6	−164.3 (4)	C13—C18—N6—C17	178.6 (3)
C12—C13—C18—N6	13.4 (6)	N5—C17—N6—C18	0.7 (6)
C14—C13—C18—N4	12.9 (5)	C8—C17—N6—C18	−177.1 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H4WA···O2	0.91	2.23	3.057 (7)	151
O4W—H4WB···O2^v	0.92	2.23	3.082 (7)	155

Symmetry code: (v) −x−1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₈H₁₂N₆)]NO₃·H₂O
M_r	455.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.917 (2), 8.7409 (17), 22.499 (6)
β (°)	107.43 (3)
V (Å³)	1860.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku SCX-mini diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.736, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18394, 4262, 2717
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.125, 1.09
No. of reflections	4262
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H4WA···O2	0.91	2.23	3.057 (7)	151
O4W—H4WB···O2ⁱ	0.92	2.23	3.082 (7)	155

Symmetry code: (i) −x−1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (project approval No. 20974053).

References

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