Aqua­(2,2′-bipyridine-κ2N,N′)bis­(4-iodo­benzoato-κO)copper(II)

Mohamadin, M.I.; Abdullah, N.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810044995

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1530

https://doi.org/10.1107/S1600536810044995

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Aqua(2,2′-bipyridine-κ²N,N′)bis(4-iodobenzoato-κO)copper(II)

Mohamad Isa Mohamadin,^a Norbani Abdullah,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 October 2010; accepted 3 November 2010; online 10 November 2010)

The Cu^II atom in the title compound, [Cu(C₇H₄IO₂)₂(C₁₀H₈N₂)(H₂O)], is N,N′-chelated by a 2,2′-bipyridine ligand and is coordinated by two monodentate carboxylate ions and a water molecule in a distorted square-pyramidal geometry. The apical site is occupied by one of the carboxylate O atoms. The water molecule forms intramolecular hydrogen bonds to the uncoordinated carboxyl O atoms. The crystal studied was a nonmerohedral twin with minor components in 0.381 (3) and 0.108 (2) proportions.

Related literature

For related copper carboxylate–2,2′-bipyridine adducts, see: He et al. (2007 ); Li et al. (2006 ); Liu et al. (2006 ); Yang et al. (1994 ).

Experimental

Crystal data

[Cu(C₇H₄IO₂)₂(C₁₀H₈N₂)(H₂O)]
M_r = 731.74
Monoclinic, P 2₁ /c
a = 13.0571 (2) Å
b = 16.0724 (2) Å
c = 11.9605 (2) Å
β = 103.298 (1)°
V = 2442.72 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.46 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2009 ) T_min = 0.355, T_max = 0.745
33957 measured reflections
5698 independent reflections
4505 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.175
S = 1.08
5698 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 1.71 e Å⁻³
Δρ_min = −1.69 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	1.982 (7)
Cu1—N2	2.009 (6)
Cu1—O1	1.977 (5)
Cu1—O3	2.216 (6)
Cu1—O1W	1.959 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O2	0.84	1.79	2.560 (9)	152
O1w—H12⋯O4	0.84	1.79	2.575 (8)	154

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536810044995/xu5068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044995/xu5068Isup2.hkl

checkCIF report

Comment top

Copper(II) benzoate and its analogs form adducts with 2,2'-bipyridine. The copper benzoate homolog furnishes a water-coordinated adduct (Yang et al., 1994), as does copper p-toluate (Li et al., 2006; Liu et al., 2006) and copper o-toluate (He et al., 2007). The copper atom in Cu(H₂O)(C₁₀H₈N₂)(C₇H₄IO₂)₂ (Scheme I) is chelated by the N-heterocycle and is coordinated by two monodentate carboxylate ions and a water molecule in a square-pyramidal geometry (Fig. 1). The apical site is occupied by the O atom of the carboxylate unit. The crystal studied is a non-merohedral twin with minor components in a 0.381 (3) and 0.108 (2) proportion.

Related literature top

For related copper carboxylate–2,2'-bipyridine adducts, see: He et al. (2007); Li et al. (2006); Liu et al. (2006); Yang et al. (1994).

Experimental top

Copper acetate monohydrate (2.00 g, 10 mmol) and 4-iodobenzoic acid (4.96 g, 20 mmol) were heated in aqueous ethanol (1:1, 60 ml) for 1 h. The solvent was removed to give blue copper bis(4-iodobenzoate), which was isolated in 50% yield. The powder and 2,2'-bipyridine (0.77 g, 5 mmol) were dissolved in tetrahydrofuran. Crystals were isolated after several days.

Structure description top

For related copper carboxylate–2,2'-bipyridine adducts, see: He et al. (2007); Li et al. (2006); Liu et al. (2006); Yang et al. (1994).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 Cu(H₂O)(C₁₀H₈N₂)(C₇H₄IO₂)₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Aqua(2,2'-bipyridine-κ²N,N')bis(4-iodobenzoato- κO)copper(II) top

Crystal data top

[Cu(C₇H₄IO₂)₂(C₁₀H₈N₂)(H₂O)]	F(000) = 1404
M_r = 731.74	D_x = 1.990 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1215 reflections
a = 13.0571 (2) Å	θ = 2.5–24.2°
b = 16.0724 (2) Å	µ = 3.46 mm⁻¹
c = 11.9605 (2) Å	T = 100 K
β = 103.298 (1)°	Cube, blue
V = 2442.72 (6) Å³	0.30 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5698 independent reflections
Radiation source: fine-focus sealed tube	4505 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (TWINABS; Bruker, 2009)	h = −15→15
T_min = 0.423, T_max = 0.423	k = 0→19
33957 measured reflections	l = 0→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.087P)² + 12.0788P] where P = (F_o² + 2F_c²)/3
5698 reflections	(Δ/σ)_max = 0.001
310 parameters	Δρ_max = 1.71 e Å⁻³
0 restraints	Δρ_min = −1.69 e Å⁻³

Crystal data top

[Cu(C₇H₄IO₂)₂(C₁₀H₈N₂)(H₂O)]	V = 2442.72 (6) Å³
M_r = 731.74	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0571 (2) Å	µ = 3.46 mm⁻¹
b = 16.0724 (2) Å	T = 100 K
c = 11.9605 (2) Å	0.30 × 0.30 × 0.30 mm
β = 103.298 (1)°

Data collection top

Bruker SMART APEX diffractometer	5698 independent reflections
Absorption correction: multi-scan (TWINABS; Bruker, 2009)	4505 reflections with I > 2σ(I)
T_min = 0.423, T_max = 0.423	R_int = 0.092
33957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.087P)² + 12.0788P] where P = (F_o² + 2F_c²)/3
5698 reflections	Δρ_max = 1.71 e Å⁻³
310 parameters	Δρ_min = −1.69 e Å⁻³

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

	x	y	z	U_iso*/U_eq
I1	1.52100 (5)	0.77933 (4)	0.96178 (5)	0.0307 (2)
I2	0.54254 (5)	1.06313 (4)	0.81444 (6)	0.0370 (2)
Cu1	0.88404 (8)	0.70624 (6)	0.44393 (8)	0.0165 (3)
O1	0.7975 (5)	0.7791 (3)	0.5186 (5)	0.0189 (13)
O2	0.7765 (5)	0.8878 (4)	0.3970 (6)	0.0319 (16)
O3	1.0368 (4)	0.7208 (3)	0.5695 (5)	0.0182 (12)
O4	1.0982 (5)	0.8248 (4)	0.4776 (5)	0.0220 (13)
O1W	0.9172 (5)	0.7943 (3)	0.3446 (5)	0.0203 (13)
H11	0.8773	0.8352	0.3455	0.030*
H12	0.9801	0.8092	0.3687	0.030*
N1	0.8380 (5)	0.6058 (4)	0.5151 (6)	0.0162 (15)
N2	0.9245 (5)	0.6191 (4)	0.3416 (5)	0.0144 (14)
C1	0.7637 (7)	0.8513 (5)	0.4846 (8)	0.0215 (19)
C2	0.7064 (7)	0.8978 (5)	0.5618 (7)	0.0209 (18)
C3	0.6627 (7)	0.9757 (5)	0.5274 (8)	0.024 (2)
H3	0.6656	0.9967	0.4540	0.029*
C4	0.6158 (7)	1.0224 (6)	0.5975 (8)	0.028 (2)
H4	0.5884	1.0759	0.5737	0.034*
C5	0.6090 (7)	0.9913 (5)	0.7019 (8)	0.0236 (19)
C6	0.6510 (7)	0.9127 (5)	0.7390 (8)	0.026 (2)
H6	0.6470	0.8919	0.8122	0.031*
C7	0.6977 (7)	0.8665 (5)	0.6682 (7)	0.0219 (19)
H7	0.7245	0.8128	0.6916	0.026*
C8	1.1036 (7)	0.7747 (5)	0.5605 (7)	0.0195 (18)
C9	1.2009 (7)	0.7822 (5)	0.6583 (7)	0.0171 (17)
C10	1.2850 (7)	0.8289 (5)	0.6483 (7)	0.0217 (19)
H10	1.2808	0.8612	0.5809	0.026*
C11	1.3773 (7)	0.8306 (5)	0.7346 (7)	0.0222 (19)
H11A	1.4365	0.8623	0.7263	0.027*
C12	1.3794 (7)	0.7842 (5)	0.8332 (7)	0.0216 (19)
C13	1.2941 (7)	0.7393 (5)	0.8471 (8)	0.0235 (19)
H13	1.2969	0.7096	0.9164	0.028*
C14	1.2052 (7)	0.7373 (5)	0.7612 (7)	0.0204 (18)
H14	1.1460	0.7059	0.7703	0.024*
C15	0.7940 (7)	0.6048 (5)	0.6056 (7)	0.0218 (19)
H15	0.7804	0.6566	0.6378	0.026*
C16	0.7670 (8)	0.5324 (5)	0.6550 (8)	0.025 (2)
H16	0.7364	0.5339	0.7198	0.030*
C17	0.7866 (7)	0.4578 (6)	0.6057 (8)	0.026 (2)
H17	0.7687	0.4068	0.6365	0.031*
C18	0.8320 (7)	0.4570 (5)	0.5122 (8)	0.0230 (19)
H18	0.8456	0.4059	0.4782	0.028*
C19	0.8573 (6)	0.5329 (5)	0.4690 (7)	0.0152 (17)
C20	0.9038 (6)	0.5399 (5)	0.3673 (7)	0.0166 (17)
C21	0.9213 (7)	0.4734 (5)	0.3003 (8)	0.026 (2)
H21	0.9065	0.4181	0.3200	0.031*
C22	0.9603 (8)	0.4886 (6)	0.2050 (7)	0.026 (2)
H22	0.9734	0.4439	0.1582	0.031*
C23	0.9802 (7)	0.5701 (5)	0.1779 (8)	0.024 (2)
H23	1.0054	0.5821	0.1112	0.029*
C24	0.9627 (6)	0.6336 (5)	0.2493 (7)	0.0195 (18)
H24	0.9784	0.6892	0.2320	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0258 (3)	0.0370 (4)	0.0256 (4)	0.0053 (3)	−0.0018 (2)	−0.0007 (2)
I2	0.0303 (4)	0.0424 (4)	0.0393 (4)	0.0066 (3)	0.0099 (3)	−0.0150 (3)
Cu1	0.0216 (6)	0.0126 (5)	0.0153 (5)	−0.0010 (4)	0.0045 (4)	0.0007 (4)
O1	0.026 (3)	0.016 (3)	0.015 (3)	0.000 (2)	0.007 (3)	−0.004 (2)
O2	0.039 (4)	0.029 (4)	0.032 (4)	0.010 (3)	0.017 (3)	0.017 (3)
O3	0.017 (3)	0.020 (3)	0.015 (3)	−0.002 (2)	0.000 (2)	0.000 (2)
O4	0.025 (3)	0.021 (3)	0.019 (3)	−0.007 (3)	0.003 (3)	0.008 (2)
O1W	0.025 (3)	0.017 (3)	0.018 (3)	0.000 (2)	0.002 (3)	0.001 (2)
N1	0.020 (4)	0.010 (3)	0.017 (4)	−0.003 (3)	0.000 (3)	−0.001 (3)
N2	0.016 (3)	0.017 (4)	0.008 (3)	0.003 (3)	0.000 (3)	0.001 (3)
C1	0.016 (4)	0.020 (5)	0.028 (5)	0.004 (3)	0.005 (4)	0.007 (4)
C2	0.017 (4)	0.020 (4)	0.025 (5)	−0.001 (3)	0.002 (4)	0.000 (3)
C3	0.025 (5)	0.023 (5)	0.026 (5)	0.000 (4)	0.008 (4)	0.004 (3)
C4	0.022 (5)	0.026 (5)	0.036 (6)	0.001 (4)	0.006 (4)	−0.003 (4)
C5	0.015 (4)	0.026 (5)	0.027 (5)	0.003 (4)	−0.001 (4)	−0.011 (4)
C6	0.021 (5)	0.022 (5)	0.036 (6)	−0.001 (4)	0.009 (4)	0.001 (4)
C7	0.017 (4)	0.017 (4)	0.027 (5)	0.001 (3)	−0.007 (4)	−0.002 (3)
C8	0.023 (5)	0.015 (4)	0.022 (5)	0.003 (4)	0.008 (4)	−0.004 (3)
C9	0.020 (4)	0.019 (4)	0.014 (4)	0.004 (3)	0.005 (3)	0.002 (3)
C10	0.030 (5)	0.024 (5)	0.013 (4)	0.002 (4)	0.009 (4)	0.000 (3)
C11	0.019 (4)	0.032 (5)	0.017 (4)	−0.005 (4)	0.007 (4)	−0.006 (3)
C12	0.029 (5)	0.022 (4)	0.015 (4)	0.009 (4)	0.007 (4)	−0.008 (3)
C13	0.026 (5)	0.019 (4)	0.025 (5)	0.005 (4)	0.004 (4)	−0.001 (3)
C14	0.025 (5)	0.012 (4)	0.024 (5)	0.004 (3)	0.006 (4)	−0.002 (3)
C15	0.024 (5)	0.017 (4)	0.024 (5)	0.000 (4)	0.004 (4)	−0.001 (3)
C16	0.034 (5)	0.023 (5)	0.019 (5)	−0.004 (4)	0.008 (4)	0.002 (3)
C17	0.028 (5)	0.027 (5)	0.023 (5)	−0.006 (4)	0.008 (4)	0.006 (4)
C18	0.019 (5)	0.013 (4)	0.037 (5)	0.003 (3)	0.006 (4)	0.003 (4)
C19	0.010 (4)	0.019 (4)	0.015 (4)	0.004 (3)	−0.002 (3)	0.004 (3)
C20	0.016 (4)	0.014 (4)	0.019 (5)	0.001 (3)	0.000 (3)	0.000 (3)
C21	0.031 (5)	0.017 (5)	0.029 (5)	−0.005 (4)	0.006 (4)	0.002 (3)
C22	0.035 (5)	0.023 (5)	0.020 (5)	0.002 (4)	0.007 (4)	−0.006 (4)
C23	0.023 (5)	0.028 (5)	0.020 (5)	0.002 (4)	0.002 (4)	0.004 (4)
C24	0.019 (4)	0.025 (5)	0.017 (5)	0.002 (4)	0.009 (4)	−0.001 (3)

Geometric parameters (Å, º) top

I1—C12	2.117 (9)	C8—C9	1.521 (12)
I2—C5	2.106 (8)	C9—C10	1.358 (12)
Cu1—N1	1.982 (7)	C9—C14	1.416 (11)
Cu1—N2	2.009 (6)	C10—C11	1.395 (12)
Cu1—O1	1.977 (5)	C10—H10	0.9500
Cu1—O3	2.216 (6)	C11—C12	1.390 (12)
Cu1—O1W	1.959 (5)	C11—H11A	0.9500
O1—C1	1.275 (10)	C12—C13	1.369 (13)
O2—C1	1.246 (10)	C13—C14	1.363 (12)
O3—C8	1.251 (10)	C13—H13	0.9500
O4—C8	1.268 (10)	C14—H14	0.9500
O1W—H11	0.8400	C15—C16	1.387 (12)
O1W—H12	0.8400	C15—H15	0.9500
N1—C15	1.338 (11)	C16—C17	1.386 (12)
N1—C19	1.344 (10)	C16—H16	0.9500
N2—C24	1.332 (10)	C17—C18	1.380 (12)
N2—C20	1.351 (10)	C17—H17	0.9500
C1—C2	1.513 (12)	C18—C19	1.394 (11)
C2—C7	1.396 (12)	C18—H18	0.9500
C2—C3	1.397 (12)	C19—C20	1.484 (12)
C3—C4	1.369 (12)	C20—C21	1.386 (12)
C3—H3	0.9500	C21—C22	1.373 (12)
C4—C5	1.367 (13)	C21—H21	0.9500
C4—H4	0.9500	C22—C23	1.389 (13)
C5—C6	1.409 (12)	C22—H22	0.9500
C6—C7	1.370 (12)	C23—C24	1.383 (12)
C6—H6	0.9500	C23—H23	0.9500
C7—H7	0.9500	C24—H24	0.9500

O1W—Cu1—O1	94.3 (2)	C14—C9—C8	119.1 (7)
O1W—Cu1—N1	168.6 (3)	C9—C10—C11	121.6 (8)
O1—Cu1—N1	91.6 (3)	C9—C10—H10	119.2
O1W—Cu1—N2	90.5 (3)	C11—C10—H10	119.2
O1—Cu1—N2	161.0 (3)	C12—C11—C10	117.5 (8)
N1—Cu1—N2	80.9 (3)	C12—C11—H11A	121.3
O1W—Cu1—O3	92.6 (2)	C10—C11—H11A	121.3
O1—Cu1—O3	98.7 (2)	C13—C12—C11	121.9 (8)
N1—Cu1—O3	96.3 (2)	C13—C12—I1	119.4 (6)
N2—Cu1—O3	99.5 (2)	C11—C12—I1	118.6 (7)
C1—O1—Cu1	126.0 (5)	C14—C13—C12	119.8 (8)
C8—O3—Cu1	123.5 (5)	C14—C13—H13	120.1
Cu1—O1W—H11	109.5	C12—C13—H13	120.1
Cu1—O1W—H12	109.5	C13—C14—C9	120.0 (8)
H11—O1W—H12	109.5	C13—C14—H14	120.0
C15—N1—C19	118.6 (7)	C9—C14—H14	120.0
C15—N1—Cu1	125.9 (5)	N1—C15—C16	123.6 (8)
C19—N1—Cu1	115.5 (5)	N1—C15—H15	118.2
C24—N2—C20	119.1 (7)	C16—C15—H15	118.2
C24—N2—Cu1	125.7 (6)	C17—C16—C15	117.1 (8)
C20—N2—Cu1	115.1 (5)	C17—C16—H16	121.5
O2—C1—O1	126.4 (8)	C15—C16—H16	121.5
O2—C1—C2	117.5 (7)	C18—C17—C16	120.6 (8)
O1—C1—C2	116.1 (7)	C18—C17—H17	119.7
C7—C2—C3	118.5 (8)	C16—C17—H17	119.7
C7—C2—C1	122.2 (8)	C17—C18—C19	118.3 (8)
C3—C2—C1	119.3 (7)	C17—C18—H18	120.9
C4—C3—C2	121.4 (8)	C19—C18—H18	120.9
C4—C3—H3	119.3	N1—C19—C18	121.9 (7)
C2—C3—H3	119.3	N1—C19—C20	114.9 (7)
C5—C4—C3	119.4 (9)	C18—C19—C20	123.2 (7)
C5—C4—H4	120.3	N2—C20—C21	121.8 (7)
C3—C4—H4	120.3	N2—C20—C19	113.5 (7)
C4—C5—C6	120.9 (8)	C21—C20—C19	124.6 (7)
C4—C5—I2	120.5 (7)	C22—C21—C20	119.0 (8)
C6—C5—I2	118.6 (6)	C22—C21—H21	120.5
C7—C6—C5	119.2 (8)	C20—C21—H21	120.5
C7—C6—H6	120.4	C21—C22—C23	119.1 (8)
C5—C6—H6	120.4	C21—C22—H22	120.4
C6—C7—C2	120.6 (8)	C23—C22—H22	120.4
C6—C7—H7	119.7	C24—C23—C22	119.1 (8)
C2—C7—H7	119.7	C24—C23—H23	120.5
O3—C8—O4	126.4 (8)	C22—C23—H23	120.5
O3—C8—C9	117.7 (7)	N2—C24—C23	121.9 (8)
O4—C8—C9	115.9 (7)	N2—C24—H24	119.0
C10—C9—C14	119.1 (8)	C23—C24—H24	119.0
C10—C9—C8	121.7 (7)

O1W—Cu1—O1—C1	13.0 (7)	Cu1—O3—C8—C9	174.9 (5)
N1—Cu1—O1—C1	−157.2 (7)	O3—C8—C9—C10	169.1 (8)
N2—Cu1—O1—C1	−91.2 (10)	O4—C8—C9—C10	−11.3 (11)
O3—Cu1—O1—C1	106.2 (7)	O3—C8—C9—C14	−9.0 (11)
O1W—Cu1—O3—C8	2.8 (6)	O4—C8—C9—C14	170.5 (7)
O1—Cu1—O3—C8	−91.9 (6)	C14—C9—C10—C11	3.1 (12)
N1—Cu1—O3—C8	175.6 (6)	C8—C9—C10—C11	−175.0 (7)
N2—Cu1—O3—C8	93.8 (6)	C9—C10—C11—C12	−1.6 (12)
O1W—Cu1—N1—C15	−138.5 (12)	C10—C11—C12—C13	−1.0 (12)
O1—Cu1—N1—C15	−17.7 (7)	C10—C11—C12—I1	176.3 (6)
N2—Cu1—N1—C15	179.8 (7)	C11—C12—C13—C14	2.0 (12)
O3—Cu1—N1—C15	81.2 (7)	I1—C12—C13—C14	−175.3 (6)
O1W—Cu1—N1—C19	44.0 (17)	C12—C13—C14—C9	−0.5 (12)
O1—Cu1—N1—C19	164.8 (6)	C10—C9—C14—C13	−2.1 (12)
N2—Cu1—N1—C19	2.3 (6)	C8—C9—C14—C13	176.1 (7)
O3—Cu1—N1—C19	−96.3 (6)	C19—N1—C15—C16	0.1 (13)
O1W—Cu1—N2—C24	2.9 (7)	Cu1—N1—C15—C16	−177.3 (7)
O1—Cu1—N2—C24	107.7 (9)	N1—C15—C16—C17	−0.6 (14)
N1—Cu1—N2—C24	175.3 (7)	C15—C16—C17—C18	0.6 (14)
O3—Cu1—N2—C24	−89.8 (7)	C16—C17—C18—C19	0.0 (14)
O1W—Cu1—N2—C20	−172.7 (6)	C15—N1—C19—C18	0.5 (12)
O1—Cu1—N2—C20	−68.0 (10)	Cu1—N1—C19—C18	178.2 (6)
N1—Cu1—N2—C20	−0.3 (6)	C15—N1—C19—C20	178.5 (7)
O3—Cu1—N2—C20	94.6 (6)	Cu1—N1—C19—C20	−3.8 (9)
Cu1—O1—C1—O2	2.1 (13)	C17—C18—C19—N1	−0.6 (13)
Cu1—O1—C1—C2	−175.2 (5)	C17—C18—C19—C20	−178.4 (8)
O2—C1—C2—C7	−172.9 (8)	C24—N2—C20—C21	0.1 (12)
O1—C1—C2—C7	4.7 (12)	Cu1—N2—C20—C21	176.0 (7)
O2—C1—C2—C3	5.4 (13)	C24—N2—C20—C19	−177.5 (7)
O1—C1—C2—C3	−177.0 (8)	Cu1—N2—C20—C19	−1.5 (9)
C7—C2—C3—C4	2.5 (13)	N1—C19—C20—N2	3.5 (11)
C1—C2—C3—C4	−175.9 (9)	C18—C19—C20—N2	−178.6 (8)
C2—C3—C4—C5	−1.8 (14)	N1—C19—C20—C21	−174.0 (8)
C3—C4—C5—C6	1.1 (14)	C18—C19—C20—C21	4.0 (14)
C3—C4—C5—I2	177.7 (7)	N2—C20—C21—C22	−0.3 (14)
C4—C5—C6—C7	−1.1 (13)	C19—C20—C21—C22	176.9 (8)
I2—C5—C6—C7	−177.8 (7)	C20—C21—C22—C23	−0.6 (14)
C5—C6—C7—C2	1.7 (13)	C21—C22—C23—C24	1.6 (14)
C3—C2—C7—C6	−2.4 (13)	C20—N2—C24—C23	1.1 (13)
C1—C2—C7—C6	175.9 (8)	Cu1—N2—C24—C23	−174.4 (6)
Cu1—O3—C8—O4	−4.6 (12)	C22—C23—C24—N2	−1.9 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2	0.84	1.79	2.560 (9)	152
O1w—H12···O4	0.84	1.79	2.575 (8)	154

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₄IO₂)₂(C₁₀H₈N₂)(H₂O)]
M_r	731.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.0571 (2), 16.0724 (2), 11.9605 (2)
β (°)	103.298 (1)
V (Å³)	2442.72 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.46
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (TWINABS; Bruker, 2009)
T_min, T_max	0.423, 0.423
No. of measured, independent and observed [I > 2σ(I)] reflections	33957, 5698, 4505
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.175, 1.08
No. of reflections	5698
No. of parameters	310
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.087P)² + 12.0788P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.71, −1.69

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—N1	1.982 (7)	Cu1—O3	2.216 (6)
Cu1—N2	2.009 (6)	Cu1—O1W	1.959 (5)
Cu1—O1	1.977 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2	0.84	1.79	2.560 (9)	151.9
O1w—H12···O4	0.84	1.79	2.575 (8)	153.9

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, X.-M., Li, C.-H., Yang, Y.-Q. & Li, W. (2007). Chin. J. Struct. Chem. 26, 206–210. CAS Google Scholar
Li, W., Li, C.-H., Yang, Y.-Q., Kuang, D.-Z. & Xu, W.-J. (2006). Chin. J. Struct. Chem. 25, 616–620. CAS Google Scholar
Liu, F.-Q., Wang, Q.-X., Jiao, K., Jian, F.-F., Liu, G.-Y. & Li, R.-X. (2006). Inorg. Chim. Acta, 359, 1524–1530. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, R.-N., Wang, D.-M., Jin, D.-M., Wang, H.-Q. & Yang, Y. (1994). Chin. J. Struct. Chem. 13, 45–47. CAS Google Scholar