Bis(μ-3-nitro­phthalato-κ2O1:O2)bis­[aqua­(2,2′-bipyridine-κ2N,N′)copper(II)] dihydrate

Han, Y.-F.; Cheng, C.; Ng, S.W.

doi:10.1107/S1600536810043229

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1484

https://doi.org/10.1107/S1600536810043229

Open

access

Bis(μ-3-nitrophthalato-κ²O¹:O²)bis[aqua(2,2′-bipyridine-κ²N,N′)copper(II)] dihydrate

Yin-Feng Han,^a Chen Cheng ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Science, Baoji 721013, People's Republic of China, ^bDepartment of Biotechnology, Wulanchabu Vocational College, Wulanchabu 012000, Inner Mongolia, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 October 2010; accepted 23 October 2010; online 30 October 2010)

Two 3-nitrophthalate dianions bridge two water-coordinated 2,2′-bipyridine-chelated Cu^II atoms about a center of inversion to generate the title dinuclear compound, [Cu₂(C₈H₃NO₆)₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O. The geometry of the Cu^II atom is a distorted square pyramid. Adjacent molecules are linked through the coordinated and solvent water molecules to form a linear ribbon running along the a axis of the monoclinic unit cell.

Related literature

For the isostructural zinc analog, see: Song et al. (2007 ).

Experimental

Crystal data

[Cu₂(C₈H₃NO₆)₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O
M_r = 929.74
Triclinic, $[P \overline 1]$
a = 7.534 (2) Å
b = 10.467 (3) Å
c = 12.044 (3) Å
α = 87.835 (2)°
β = 74.911 (3)°
γ = 77.437 (3)°
V = 894.9 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 295 K
0.45 × 0.45 × 0.40 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.591, T_max = 0.629
4675 measured reflections
3092 independent reflections
2732 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.01
3092 reflections
284 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.967 (2)
Cu1—O3ⁱ	2.172 (2)
Cu1—O1w	1.994 (2)
Cu1—N2	2.029 (2)
Cu1—N3	2.013 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O2w	0.83 (3)	1.85 (1)	2.660 (3)	166 (3)
O1w—H12⋯O4ⁱⁱ	0.83 (3)	1.90 (1)	2.718 (3)	168 (3)
O2w—H21⋯O4	0.84 (3)	2.04 (2)	2.830 (3)	158 (3)
O2w—H22⋯O1ⁱ	0.84 (3)	2.25 (2)	2.985 (3)	146 (3)
O2w—H22⋯O3ⁱ	0.84 (3)	2.35 (3)	2.977 (3)	132 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043229/xu5061sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043229/xu5061Isup2.hkl

checkCIF report

Comment top

Dinuclear Zn₂(H₂O)₂(C₁₀H₈N₂)₂(C₈H₃NO₆)₂^.2H₂O is reported to exhibit intense fluorescence. In its crystal structure, the 3-nitrophthalate dianion bridges two water-coordinated, 2,2'-bipyridine-chelated zinc atoms about a center-of-inversion; the geometry of the zinc atom is a square pyramid (Song et al., 2007). The present copper analog (Scheme I, Fig. 1) is isostructural, the two compounds crystallizing with matching cell dimensions. Adjacent molecules are connected to the lattice water molecule by hydrogen bonds to form a linear ribbon running along the a-axis of the monoclinic unit cell (Fig. 2).

Related literature top

For the isostructural zinc analog, see: Song et al. (2007).

Experimental top

3-Nitrophthalic acid (0.105 g), 2,2'-bipyridine (0.078 g), copper chloride dihydrate (0.085 g) and water (2 ml) were heated at 393 K in a 25 ml, Teflon-lined, stainless-steel Parr bomb for 3 days. Blue crystal were isolated. CH&N elemental analysis. Found: C 46.32, H 3.17, N 9.11%. Calc.: C 46.51, H 3.25, N 9.04%.

Structure description top

For the isostructural zinc analog, see: Song et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of dinuclear Cu₂(H₂O)₂(C₁₀H₈N₂)₂(C₈H₃NO₆)₂^.2H₂O at the 50% probability evel; hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain.

Bis(µ-3-nitrophthalato-κ²O¹:O²)bis[aqua(2,2'- bipyridine-κ²N,N')copper(II)] dihydrate top

Crystal data top

[Cu₂(C₈H₃NO₆)₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O	Z = 1
M_r = 929.74	F(000) = 474
Triclinic, P1	D_x = 1.725 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.534 (2) Å	Cell parameters from 3039 reflections
b = 10.467 (3) Å	θ = 2.6–28.1°
c = 12.044 (3) Å	µ = 1.28 mm⁻¹
α = 87.835 (2)°	T = 295 K
β = 74.911 (3)°	Block, blue
γ = 77.437 (3)°	0.45 × 0.45 × 0.40 mm
V = 894.9 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	3092 independent reflections
Radiation source: fine-focus sealed tube	2732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
T_min = 0.591, T_max = 0.629	k = −11→12
4675 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0456P)² + 0.6587P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3092 reflections	Δρ_max = 0.54 e Å⁻³
284 parameters	Δρ_min = −0.55 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (3)

Crystal data top

[Cu₂(C₈H₃NO₆)₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O	γ = 77.437 (3)°
M_r = 929.74	V = 894.9 (4) Å³
Triclinic, P1	Z = 1
a = 7.534 (2) Å	Mo Kα radiation
b = 10.467 (3) Å	µ = 1.28 mm⁻¹
c = 12.044 (3) Å	T = 295 K
α = 87.835 (2)°	0.45 × 0.45 × 0.40 mm
β = 74.911 (3)°

Data collection top

Bruker SMART APEX diffractometer	3092 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2732 reflections with I > 2σ(I)
T_min = 0.591, T_max = 0.629	R_int = 0.023
4675 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	6 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.54 e Å⁻³
3092 reflections	Δρ_min = −0.55 e Å⁻³
284 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.21328 (4)	0.56513 (3)	0.71332 (2)	0.02412 (15)
N1	0.4799 (3)	0.0616 (2)	0.2658 (2)	0.0343 (6)
N2	0.2998 (3)	0.4783 (2)	0.84926 (18)	0.0257 (5)
N3	0.0759 (3)	0.7029 (2)	0.83612 (19)	0.0281 (5)
O1	0.3115 (3)	0.41035 (18)	0.61015 (15)	0.0280 (4)
O2	0.0466 (3)	0.3577 (2)	0.71082 (17)	0.0409 (5)
O3	0.5866 (2)	0.32313 (18)	0.38170 (15)	0.0288 (4)
O4	0.3075 (3)	0.39837 (18)	0.34247 (16)	0.0305 (4)
O5	0.5574 (4)	0.1439 (2)	0.2160 (2)	0.0633 (8)
O6	0.4884 (5)	−0.0410 (3)	0.2191 (2)	0.0874 (11)
O1W	0.0433 (3)	0.6507 (2)	0.61730 (16)	0.0332 (5)
H11	0.105 (4)	0.646 (3)	0.5489 (12)	0.050*
H12	−0.056 (3)	0.625 (3)	0.626 (2)	0.050*
O2W	0.2753 (3)	0.6602 (2)	0.41019 (18)	0.0385 (5)
H21	0.279 (4)	0.593 (2)	0.374 (3)	0.058*
H22	0.372 (3)	0.650 (3)	0.435 (3)	0.058*
C1	0.1932 (4)	0.3366 (3)	0.6318 (2)	0.0256 (6)
C2	0.2383 (4)	0.2132 (2)	0.5588 (2)	0.0230 (5)
C3	0.1636 (4)	0.1084 (3)	0.6101 (2)	0.0333 (7)
H3	0.0890	0.1179	0.6854	0.040*
C4	0.1973 (4)	−0.0096 (3)	0.5522 (3)	0.0389 (7)
H4	0.1505	−0.0795	0.5892	0.047*
C5	0.3010 (4)	−0.0224 (3)	0.4391 (3)	0.0350 (7)
H5	0.3223	−0.1002	0.3981	0.042*
C6	0.3725 (4)	0.0823 (3)	0.3879 (2)	0.0257 (6)
C7	0.3471 (3)	0.2024 (2)	0.4442 (2)	0.0210 (5)
C8	0.4222 (4)	0.3186 (2)	0.3836 (2)	0.0213 (5)
C9	0.4136 (4)	0.3603 (3)	0.8485 (2)	0.0330 (6)
H9	0.4684	0.3147	0.7789	0.040*
C10	0.4522 (4)	0.3043 (3)	0.9478 (3)	0.0379 (7)
H10	0.5333	0.2229	0.9445	0.045*
C11	0.3696 (4)	0.3698 (3)	1.0513 (3)	0.0383 (7)
H11A	0.3934	0.3332	1.1189	0.046*
C12	0.2507 (4)	0.4911 (3)	1.0534 (2)	0.0340 (7)
H12A	0.1921	0.5369	1.1225	0.041*
C13	0.2199 (4)	0.5435 (3)	0.9505 (2)	0.0266 (6)
C14	0.0971 (4)	0.6732 (3)	0.9424 (2)	0.0281 (6)
C15	0.0074 (4)	0.7584 (3)	1.0353 (3)	0.0395 (7)
H15	0.0244	0.7368	1.1080	0.047*
C16	−0.1067 (5)	0.8752 (3)	1.0185 (3)	0.0474 (8)
H16	−0.1691	0.9332	1.0799	0.057*
C17	−0.1276 (5)	0.9055 (3)	0.9093 (3)	0.0483 (8)
H17	−0.2030	0.9845	0.8961	0.058*
C18	−0.0351 (5)	0.8171 (3)	0.8207 (3)	0.0396 (7)
H18	−0.0501	0.8374	0.7474	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0282 (2)	0.0265 (2)	0.01756 (19)	−0.00328 (14)	−0.00774 (13)	−0.00078 (12)
N1	0.0379 (14)	0.0317 (14)	0.0318 (13)	−0.0003 (11)	−0.0108 (11)	−0.0096 (11)
N2	0.0292 (12)	0.0285 (12)	0.0210 (11)	−0.0074 (10)	−0.0082 (9)	−0.0014 (9)
N3	0.0317 (13)	0.0270 (12)	0.0242 (11)	−0.0058 (10)	−0.0051 (10)	−0.0004 (9)
O1	0.0316 (10)	0.0304 (10)	0.0225 (9)	−0.0080 (8)	−0.0057 (8)	−0.0061 (8)
O2	0.0400 (12)	0.0493 (13)	0.0274 (11)	−0.0112 (10)	0.0044 (9)	−0.0098 (9)
O3	0.0236 (10)	0.0363 (11)	0.0288 (10)	−0.0104 (8)	−0.0080 (8)	0.0044 (8)
O4	0.0328 (10)	0.0280 (10)	0.0334 (10)	−0.0040 (8)	−0.0167 (9)	0.0093 (8)
O5	0.101 (2)	0.0467 (15)	0.0320 (12)	−0.0231 (15)	0.0086 (13)	−0.0070 (11)
O6	0.125 (3)	0.0627 (18)	0.0617 (18)	−0.0406 (19)	0.0202 (18)	−0.0405 (15)
O1W	0.0281 (11)	0.0455 (12)	0.0278 (10)	−0.0052 (9)	−0.0125 (9)	0.0023 (9)
O2W	0.0421 (12)	0.0405 (12)	0.0355 (12)	−0.0119 (10)	−0.0121 (10)	−0.0007 (9)
C1	0.0316 (15)	0.0300 (14)	0.0164 (12)	−0.0039 (12)	−0.0108 (11)	0.0031 (10)
C2	0.0227 (13)	0.0254 (13)	0.0219 (13)	−0.0026 (11)	−0.0097 (11)	0.0020 (10)
C3	0.0349 (16)	0.0368 (16)	0.0281 (14)	−0.0098 (13)	−0.0073 (12)	0.0056 (12)
C4	0.0441 (18)	0.0285 (16)	0.0461 (18)	−0.0150 (14)	−0.0102 (15)	0.0105 (13)
C5	0.0362 (16)	0.0225 (14)	0.0489 (18)	−0.0047 (12)	−0.0167 (14)	−0.0022 (13)
C6	0.0237 (13)	0.0263 (14)	0.0273 (14)	0.0000 (11)	−0.0107 (11)	−0.0033 (11)
C7	0.0195 (12)	0.0221 (13)	0.0234 (13)	−0.0014 (10)	−0.0116 (10)	0.0015 (10)
C8	0.0264 (14)	0.0238 (13)	0.0145 (11)	−0.0053 (11)	−0.0062 (10)	−0.0023 (10)
C9	0.0373 (16)	0.0332 (16)	0.0279 (14)	−0.0022 (13)	−0.0114 (12)	−0.0013 (12)
C10	0.0413 (17)	0.0339 (16)	0.0432 (17)	−0.0056 (13)	−0.0223 (14)	0.0079 (13)
C11	0.0442 (18)	0.0487 (19)	0.0295 (15)	−0.0182 (15)	−0.0178 (14)	0.0138 (13)
C12	0.0375 (16)	0.0489 (18)	0.0206 (13)	−0.0177 (14)	−0.0094 (12)	0.0010 (12)
C13	0.0285 (14)	0.0326 (15)	0.0217 (13)	−0.0120 (12)	−0.0072 (11)	−0.0002 (11)
C14	0.0280 (14)	0.0323 (15)	0.0252 (14)	−0.0121 (12)	−0.0041 (11)	−0.0018 (11)
C15	0.0438 (18)	0.0445 (18)	0.0281 (15)	−0.0139 (15)	−0.0007 (13)	−0.0085 (13)
C16	0.049 (2)	0.0407 (19)	0.0447 (19)	−0.0076 (16)	0.0027 (16)	−0.0164 (15)
C17	0.048 (2)	0.0313 (17)	0.058 (2)	−0.0008 (15)	−0.0065 (17)	−0.0074 (15)
C18	0.0457 (18)	0.0313 (16)	0.0382 (17)	−0.0026 (14)	−0.0096 (14)	0.0018 (13)

Geometric parameters (Å, º) top

Cu1—O1	1.967 (2)	C3—H3	0.9300
Cu1—O3ⁱ	2.172 (2)	C4—C5	1.378 (4)
Cu1—O1w	1.994 (2)	C4—H4	0.9300
Cu1—N2	2.029 (2)	C5—C6	1.380 (4)
Cu1—N3	2.013 (2)	C5—H5	0.9300
N1—O5	1.199 (3)	C6—C7	1.403 (4)
N1—O6	1.213 (3)	C7—C8	1.533 (3)
N1—C6	1.480 (4)	C9—C10	1.383 (4)
N2—C13	1.348 (3)	C9—H9	0.9300
N2—C9	1.340 (4)	C10—C11	1.373 (4)
N3—C18	1.339 (4)	C10—H10	0.9300
N3—C14	1.347 (4)	C11—C12	1.382 (4)
O1—C1	1.274 (3)	C11—H11A	0.9300
O2—C1	1.240 (3)	C12—C13	1.390 (4)
O3—C8	1.244 (3)	C12—H12A	0.9300
O3—Cu1ⁱ	2.1722 (18)	C13—C14	1.483 (4)
O4—C8	1.252 (3)	C14—C15	1.387 (4)
O1W—H11	0.83 (3)	C15—C16	1.374 (5)
O1W—H12	0.83 (3)	C15—H15	0.9300
O2W—H21	0.84 (3)	C16—C17	1.381 (5)
O2W—H22	0.84 (3)	C16—H16	0.9300
C1—C2	1.515 (4)	C17—C18	1.374 (4)
C2—C3	1.393 (4)	C17—H17	0.9300
C2—C7	1.404 (4)	C18—H18	0.9300
C3—C4	1.382 (4)

O1—Cu1—O1W	92.15 (8)	C5—C6—C7	124.0 (3)
O1—Cu1—N3	168.62 (8)	C5—C6—N1	115.6 (2)
O1W—Cu1—N3	88.44 (9)	C7—C6—N1	120.5 (2)
O1—Cu1—N2	95.88 (8)	C2—C7—C6	116.0 (2)
O1W—Cu1—N2	160.36 (9)	C2—C7—C8	121.2 (2)
N3—Cu1—N2	80.22 (9)	C6—C7—C8	122.7 (2)
O1—Cu1—O3ⁱ	95.27 (8)	O3—C8—O4	128.0 (2)
O1W—Cu1—O3ⁱ	86.74 (8)	O3—C8—C7	117.1 (2)
N3—Cu1—O3ⁱ	96.11 (8)	O4—C8—C7	114.9 (2)
N2—Cu1—O3ⁱ	110.24 (8)	N2—C9—C10	122.1 (3)
O5—N1—O6	121.7 (3)	N2—C9—H9	119.0
O5—N1—C6	120.4 (2)	C10—C9—H9	119.0
O6—N1—C6	117.9 (3)	C11—C10—C9	119.5 (3)
C13—N2—C9	118.6 (2)	C11—C10—H10	120.3
C13—N2—Cu1	114.89 (18)	C9—C10—H10	120.3
C9—N2—Cu1	126.25 (18)	C10—C11—C12	119.0 (3)
C18—N3—C14	118.9 (2)	C10—C11—H11A	120.5
C18—N3—Cu1	125.6 (2)	C12—C11—H11A	120.5
C14—N3—Cu1	115.52 (18)	C11—C12—C13	118.9 (3)
C1—O1—Cu1	108.99 (16)	C11—C12—H12A	120.5
C8—O3—Cu1ⁱ	134.66 (17)	C13—C12—H12A	120.5
Cu1—O1W—H11	109 (2)	N2—C13—C12	121.9 (3)
Cu1—O1W—H12	116 (2)	N2—C13—C14	114.5 (2)
H11—O1W—H12	112 (2)	C12—C13—C14	123.6 (2)
H21—O2W—H22	109 (2)	N3—C14—C15	121.4 (3)
O2—C1—O1	124.0 (2)	N3—C14—C13	114.6 (2)
O2—C1—C2	118.2 (2)	C15—C14—C13	124.0 (3)
O1—C1—C2	117.7 (2)	C16—C15—C14	119.2 (3)
C3—C2—C7	120.2 (2)	C16—C15—H15	120.4
C3—C2—C1	116.7 (2)	C14—C15—H15	120.4
C7—C2—C1	123.1 (2)	C15—C16—C17	119.2 (3)
C4—C3—C2	121.8 (3)	C15—C16—H16	120.4
C4—C3—H3	119.1	C17—C16—H16	120.4
C2—C3—H3	119.1	C18—C17—C16	118.9 (3)
C3—C4—C5	119.3 (3)	C18—C17—H17	120.5
C3—C4—H4	120.3	C16—C17—H17	120.5
C5—C4—H4	120.3	N3—C18—C17	122.4 (3)
C6—C5—C4	118.8 (3)	N3—C18—H18	118.8
C6—C5—H5	120.6	C17—C18—H18	118.8
C4—C5—H5	120.6

O1—Cu1—N2—C13	−164.61 (18)	C3—C2—C7—C8	176.7 (2)
O1W—Cu1—N2—C13	−51.0 (3)	C1—C2—C7—C8	−2.3 (4)
N3—Cu1—N2—C13	4.59 (18)	C5—C6—C7—C2	−1.3 (4)
O3ⁱ—Cu1—N2—C13	97.54 (19)	N1—C6—C7—C2	178.2 (2)
O1—Cu1—N2—C9	9.4 (2)	C5—C6—C7—C8	−177.7 (2)
O1W—Cu1—N2—C9	123.1 (3)	N1—C6—C7—C8	1.8 (4)
N3—Cu1—N2—C9	178.6 (2)	Cu1ⁱ—O3—C8—O4	−14.3 (4)
O3ⁱ—Cu1—N2—C9	−88.4 (2)	Cu1ⁱ—O3—C8—C7	166.26 (16)
O1—Cu1—N3—C18	−110.3 (4)	C2—C7—C8—O3	96.7 (3)
O1W—Cu1—N3—C18	−17.1 (2)	C6—C7—C8—O3	−87.1 (3)
N2—Cu1—N3—C18	179.0 (3)	C2—C7—C8—O4	−82.8 (3)
O3ⁱ—Cu1—N3—C18	69.4 (2)	C6—C7—C8—O4	93.3 (3)
O1—Cu1—N3—C14	68.2 (5)	C13—N2—C9—C10	−0.5 (4)
O1W—Cu1—N3—C14	161.3 (2)	Cu1—N2—C9—C10	−174.3 (2)
N2—Cu1—N3—C14	−2.61 (19)	N2—C9—C10—C11	1.1 (5)
O3ⁱ—Cu1—N3—C14	−112.15 (19)	C9—C10—C11—C12	−0.5 (5)
O1W—Cu1—O1—C1	−79.31 (17)	C10—C11—C12—C13	−0.7 (4)
N3—Cu1—O1—C1	13.5 (5)	C9—N2—C13—C12	−0.7 (4)
N2—Cu1—O1—C1	82.74 (17)	Cu1—N2—C13—C12	173.8 (2)
O3ⁱ—Cu1—O1—C1	−166.23 (16)	C9—N2—C13—C14	179.8 (2)
Cu1—O1—C1—O2	−4.2 (3)	Cu1—N2—C13—C14	−5.7 (3)
Cu1—O1—C1—C2	177.93 (17)	C11—C12—C13—N2	1.3 (4)
O2—C1—C2—C3	−26.2 (4)	C11—C12—C13—C14	−179.3 (3)
O1—C1—C2—C3	151.8 (2)	C18—N3—C14—C15	−0.3 (4)
O2—C1—C2—C7	152.9 (2)	Cu1—N3—C14—C15	−178.9 (2)
O1—C1—C2—C7	−29.2 (4)	C18—N3—C14—C13	178.9 (2)
C7—C2—C3—C4	1.7 (4)	Cu1—N3—C14—C13	0.4 (3)
C1—C2—C3—C4	−179.2 (3)	N2—C13—C14—N3	3.5 (3)
C2—C3—C4—C5	−2.8 (5)	C12—C13—C14—N3	−176.0 (3)
C3—C4—C5—C6	1.7 (5)	N2—C13—C14—C15	−177.3 (3)
C4—C5—C6—C7	0.3 (4)	C12—C13—C14—C15	3.3 (4)
C4—C5—C6—N1	−179.2 (3)	N3—C14—C15—C16	0.6 (4)
O5—N1—C6—C5	−175.4 (3)	C13—C14—C15—C16	−178.6 (3)
O6—N1—C6—C5	3.8 (4)	C14—C15—C16—C17	−0.8 (5)
O5—N1—C6—C7	5.1 (4)	C15—C16—C17—C18	0.7 (5)
O6—N1—C6—C7	−175.7 (3)	C14—N3—C18—C17	0.3 (5)
C3—C2—C7—C6	0.3 (4)	Cu1—N3—C18—C17	178.7 (2)
C1—C2—C7—C6	−178.7 (2)	C16—C17—C18—N3	−0.5 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2w	0.83 (3)	1.85 (1)	2.660 (3)	166 (3)
O1w—H12···O4ⁱⁱ	0.83 (3)	1.90 (1)	2.718 (3)	168 (3)
O2w—H21···O4	0.84 (3)	2.04 (2)	2.830 (3)	158 (3)
O2w—H22···O1ⁱ	0.84 (3)	2.25 (2)	2.985 (3)	146 (3)
O2w—H22···O3ⁱ	0.84 (3)	2.35 (3)	2.977 (3)	132 (3)

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₈H₃NO₆)₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O
M_r	929.74
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.534 (2), 10.467 (3), 12.044 (3)
α, β, γ (°)	87.835 (2), 74.911 (3), 77.437 (3)
V (Å³)	894.9 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.45 × 0.45 × 0.40

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.591, 0.629
No. of measured, independent and observed [I > 2σ(I)] reflections	4675, 3092, 2732
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.01
No. of reflections	3092
No. of parameters	284
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.55

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—O1	1.967 (2)	Cu1—N2	2.029 (2)
Cu1—O3ⁱ	2.172 (2)	Cu1—N3	2.013 (2)
Cu1—O1w	1.994 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2w	0.83 (3)	1.85 (1)	2.660 (3)	166 (3)
O1w—H12···O4ⁱⁱ	0.83 (3)	1.90 (1)	2.718 (3)	168 (3)
O2w—H21···O4	0.84 (3)	2.04 (2)	2.830 (3)	158 (3)
O2w—H22···O1ⁱ	0.84 (3)	2.25 (2)	2.985 (3)	146 (3)
O2w—H22···O3ⁱ	0.84 (3)	2.35 (3)	2.977 (3)	132 (3)

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

Acknowledgements

We thank the Key Research Project, Baoji University of Arts and Sciences (grant No. ZK08114), and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2003). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). 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
Song, Y.-S., Yan, B. & Chen, Z.-X. (2007). Appl. Organomet. Chem. 21, 150–155. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.