(2,2′-Bipyridine)bis­(triphenyl­phosphine)copper(I) nitrate chloro­form solvate hemihydrate

Navarro, M.; Corona, O.A.; González, T.; Capparelli, M.V.

doi:10.1107/S1600536808006260

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m533-m534

doi:10.1107/S1600536808006260

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(2,2′-Bipyridine)bis(triphenylphosphine)copper(I) nitrate chloroform solvate hemihydrate

Maribel Navarro,^a Oscar A. Corona,^a Teresa González ^a and Mario V. Capparelli ^b ^*

^aCentro de Química, Instituto Venezolano de Investigaciones Científicas, Caracas, Venezuela, and ^bDepartamento de Química, Facultad de Ciencias, Universidad Central de Venezuela, Caracas, Venezuela
^*Correspondence e-mail: mariocapparelli@cantv.net

(Received 23 February 2008; accepted 6 March 2008; online 12 March 2008)

In the title compound, [Cu(C₁₀H₈N₂)(C₁₈H₁₅P)₂]NO₂·CHCl₃·0.5H₂O, the Cu atom is tetrahedrally coordinated by a bidentate 2,2′-bipyridine ligand and two PPh₃ ligands. The Cu—N and Cu—P distances are similar to those observed in similar compounds. The range of coordination angles shows a moderate distortion from ideal tetrahedral geometry. The bipyridine ligand is twisted [14.2 (4)°] about the ring–ring C—C bond. The nitrate anion and the water and chloroform molecules of solvation are disordered. In the crystal structure, there are O(water)—H⋯O(nitrate), C—H⋯O(water) and C—H⋯O(nitrate) hydrogen bonds.

Related literature

For related literature, see: Allen et al. (1987 ); Engelhardt et al. (1985 ); Hirshfeld (1976 ); Navarro et al. (2003 ).

Experimental

Crystal data

[Cu(C₁₀H₈N₂)(C₁₈H₁₅P)₂]NO₃·CHCl₃·0.5H₂O
M_r = 934.65
Triclinic, $[P \overline 1]$
a = 10.754 (2) Å
b = 12.672 (3) Å
c = 17.464 (4) Å
α = 99.100 (5)°
β = 99.279 (4)°
γ = 101.229 (5)°
V = 2259.4 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 296 (2) K
0.56 × 0.51 × 0.40 mm

Data collection

Rigaku AFC7S Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.584, T_max = 0.733
25842 measured reflections
8576 independent reflections
6719 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.136
S = 1.06
8576 reflections
549 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N1	2.070 (2)
Cu1—N12	2.103 (3)
Cu1—P2	2.2600 (9)
Cu1—P1	2.2659 (9)

N1—Cu1—N12	79.71 (10)
N1—Cu1—P2	111.18 (8)
N12—Cu1—P2	111.86 (7)
N1—Cu1—P1	111.46 (8)
N12—Cu1—P1	108.68 (7)
P2—Cu1—P1	124.89 (3)

N1—C6—C7—N12	14.2 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3Sⁱ	0.93	2.56	3.317 (9)	139
C5—H5⋯O1Wⁱ	0.93	2.34	3.182 (15)	151
C8—H8⋯O2Sⁱⁱ	0.93	2.38	3.242 (11)	155
C45—H45⋯O3S	0.93	2.59	3.493 (10)	163
C1S—H1S⋯O1Sⁱⁱⁱ	0.98	2.25	3.204 (7)	165
O1W⋯O2S^iv			2.663 (19)
O1W⋯O2S^v			2.667 (19)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z+1; (iv) x+1, y, z+1; (v) -x+1, -y+2, -z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006260/bg2166sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006260/bg2166Isup2.hkl

checkCIF report

Comment top

The title compound (I) was prepared within our program of studies of copper complexes containing N-bidentated aromatic ligands, focused on the search for drugs with biological activity, especially against parasitic diseases (Navarro et al., 2003).

The structure analysis showed that, in addition to the complex cation and the (partially disordered) nitrate anion the crystals contain disordered molecules of water and chloroform of solvation.

In the cation (Fig. 1), the metal atom is tetrahedrally coordinated to a bidentated 2,2'-bipyridine (bipy) ligand and to two PPh₃ moieties. The Cu—N and Cu—P (Table 1) distances are comparable to Cu—N, 2.056 (8), 2.113 (9) Å and Cu—P, 2.246 (3), 2.256 (3) Å observed in the same cation in [Cu(PPh₃)₂(bipy)]ClO₄ (Engelhardt et al., 1985). All bond lengths and angles in the organic ligands are within normal values (Allen et al., 1987).

The range of coordination angles (Table 1) shows a moderate distortion from the ideal tetrahedral geometry. As expected, the bite angle is the smaller one, while the P—Cu—P angle is the largest, due to the bulkiness of the PPh₃ moieties. The five-member metallacycle, Cu1—N1—C6—C7—N2, can be described as an envelope on C6, albeit a flat one [C6 is 0.148 (4) Å out of the plane]. The bipy ligand is twisted about C6—C7 (Table 1); the dihedral angle between both heterocycles is 17.0 (2)°.

Although the water's H atoms could not be located (see Refinement Section), short contacts with the nitrate anion [O1w···O2s(1 + x, y, z), 2.663 (19) Å; O1w···O2s(1 - x, 2 - y, -z), 2.667 (19) Å] indicate hydrogen bonds between these two groups. Further evidence of the feasibility of these links is given by the corresponding O2s···O1w···O2s angle [146.7 (5)°]. Several C—H···O bonds may also contribute to the crystal packing (Fig. 2 and Supplementary material).

Related literature top

For related literature, see: Allen et al. (1987); Engelhardt et al. (1985); Hirshfeld (1976); Navarro et al. (2003); Sheldrick (1997b); Spek (1998).

Experimental top

The title compound (I) was synthesized by the reaction of copper nitrate with bipyridine. To a solution of Cu(PPh₃)₂NO₃ (100 mg, 0.15 mmol) in dichloromethane (10 ml) was added 2,2'-bipyridine (24 mg, 0.15 mmol). The solution, initially transparent, became yellow. It was stirred for 1 h at room temperature and then was added to hexane (50 ml). The light yellow solid formed was filtered and dried (122 mg, 98%). All operations were carried out under inert atmosphere. Crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform solution.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Structure of the complex cation [Cu(PPh₃)₂(bipy)]⁺ showing the atomic numbering. Displacement parameters are drawn at 50% probability level.
	Fig. 2. Crystal structure of (I). For clarity, alternative positions for disordered atoms and H atoms were omitted. Possible hydrogen bonds are shown as dashed lines.

(2,2'-Bipyridine)bis(triphenylphosphine)copper(I) nitrate chloroform solvate hemihydrate top

Crystal data top

[Cu(C₁₀H₈N₂)(C₁₈H₁₅P)₂]NO₃·CHCl₃·0.5H₂O	Z = 2
M_r = 934.65	F(000) = 962
Triclinic, P1	D_x = 1.374 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 10.754 (2) Å	Cell parameters from 15269 reflections
b = 12.672 (3) Å	θ = 1.7–28.0°
c = 17.464 (4) Å	µ = 0.78 mm⁻¹
α = 99.100 (5)°	T = 296 K
β = 99.279 (4)°	Irregular, green
γ = 101.229 (5)°	0.56 × 0.51 × 0.40 mm
V = 2259.4 (9) Å³

Data collection top

Rigaku AFC7S Mercury diffractometer	8576 independent reflections
Radiation source: fine-focus sealed tube	6719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 14.63 pixels mm^-1	θ_max = 28.0°, θ_min = 1.2°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −16→15
T_min = 0.584, T_max = 0.733	l = −21→21
25842 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0572P)² + 1.3813P] where P = (F_o² + 2F_c²)/3
8576 reflections	(Δ/σ)_max = 0.001
549 parameters	Δρ_max = 0.49 e Å⁻³
20 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Cu(C₁₀H₈N₂)(C₁₈H₁₅P)₂]NO₃·CHCl₃·0.5H₂O	γ = 101.229 (5)°
M_r = 934.65	V = 2259.4 (9) Å³
Triclinic, P1	Z = 2
a = 10.754 (2) Å	Mo Kα radiation
b = 12.672 (3) Å	µ = 0.78 mm⁻¹
c = 17.464 (4) Å	T = 296 K
α = 99.100 (5)°	0.56 × 0.51 × 0.40 mm
β = 99.279 (4)°

Data collection top

Rigaku AFC7S Mercury diffractometer	8576 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	6719 reflections with I > 2σ(I)
T_min = 0.584, T_max = 0.733	R_int = 0.031
25842 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	20 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
8576 reflections	Δρ_min = −0.53 e Å⁻³
549 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. Refinement details for disordered atoms are given in the Refimnement section.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.56159 (3)	0.26669 (3)	0.22887 (2)	0.04336 (12)
P1	0.40007 (8)	0.34553 (6)	0.18315 (5)	0.04467 (19)
P2	0.61841 (7)	0.24899 (6)	0.35575 (4)	0.04036 (18)
N1	0.5630 (3)	0.1260 (2)	0.15089 (15)	0.0517 (6)
C2	0.4854 (4)	0.0263 (3)	0.1418 (2)	0.0661 (10)
H2	0.4128	0.0195	0.1648	0.079*
C3	0.5102 (5)	−0.0673 (3)	0.0989 (3)	0.0839 (13)
H3	0.4550	−0.1356	0.0934	0.101*
C4	0.6161 (6)	−0.0569 (4)	0.0654 (3)	0.0951 (15)
H4	0.6346	−0.1187	0.0372	0.114*
C5	0.6960 (5)	0.0441 (4)	0.0730 (2)	0.0810 (12)
H5	0.7687	0.0517	0.0500	0.097*
C6	0.6661 (3)	0.1351 (3)	0.11567 (19)	0.0555 (8)
C7	0.7456 (3)	0.2477 (3)	0.12513 (19)	0.0549 (8)
C8	0.8316 (4)	0.2757 (4)	0.0758 (2)	0.0813 (12)
H8	0.8441	0.2222	0.0367	0.098*
C9	0.8968 (4)	0.3815 (5)	0.0854 (3)	0.0913 (14)
H9	0.9547	0.4007	0.0531	0.110*
C10	0.8769 (4)	0.4593 (4)	0.1426 (3)	0.0830 (13)
H10	0.9203	0.5322	0.1495	0.100*
C11	0.7911 (3)	0.4281 (3)	0.1902 (2)	0.0625 (9)
H11	0.7791	0.4811	0.2299	0.075*
N12	0.7239 (2)	0.3238 (2)	0.18134 (15)	0.0496 (6)
C21	0.3703 (3)	0.3373 (3)	0.07633 (18)	0.0506 (7)
C22	0.2493 (4)	0.3103 (3)	0.0274 (2)	0.0727 (10)
H22	0.1753	0.2938	0.0484	0.087*
C23	0.2388 (5)	0.3081 (4)	−0.0532 (2)	0.0900 (14)
H23	0.1573	0.2884	−0.0859	0.108*
C24	0.3442 (5)	0.3339 (3)	−0.0849 (2)	0.0841 (13)
H24	0.3351	0.3340	−0.1387	0.101*
C25	0.4636 (5)	0.3597 (3)	−0.0381 (2)	0.0769 (11)
H25	0.5364	0.3766	−0.0601	0.092*
C26	0.4774 (4)	0.3610 (3)	0.0419 (2)	0.0605 (9)
H26	0.5599	0.3780	0.0733	0.073*
C31	0.2417 (3)	0.2894 (3)	0.20327 (19)	0.0506 (7)
C32	0.1871 (3)	0.1791 (3)	0.1751 (2)	0.0676 (10)
H32	0.2279	0.1370	0.1431	0.081*
C33	0.0709 (4)	0.1305 (4)	0.1943 (3)	0.0825 (12)
H33	0.0345	0.0563	0.1753	0.099*
C34	0.0109 (4)	0.1929 (5)	0.2412 (3)	0.0854 (14)
H34	−0.0662	0.1608	0.2544	0.103*
C35	0.0637 (4)	0.3019 (4)	0.2687 (3)	0.0831 (13)
H35	0.0221	0.3438	0.3001	0.100*
C36	0.1787 (3)	0.3507 (3)	0.2502 (2)	0.0633 (9)
H36	0.2140	0.4251	0.2694	0.076*
C41	0.4297 (3)	0.4929 (2)	0.22167 (19)	0.0509 (7)
C42	0.5256 (4)	0.5401 (3)	0.2877 (2)	0.0698 (10)
H42	0.5735	0.4964	0.3119	0.084*
C43	0.5515 (5)	0.6512 (4)	0.3184 (3)	0.0949 (15)
H43	0.6155	0.6819	0.3633	0.114*
C44	0.4819 (5)	0.7157 (4)	0.2822 (3)	0.0934 (14)
H44	0.5004	0.7907	0.3022	0.112*
C45	0.3853 (5)	0.6713 (3)	0.2168 (3)	0.0797 (12)
H45	0.3376	0.7158	0.1934	0.096*
C46	0.3594 (4)	0.5600 (3)	0.1862 (2)	0.0618 (9)
H46	0.2947	0.5298	0.1417	0.074*
C51	0.4918 (3)	0.1884 (2)	0.40385 (17)	0.0422 (6)
C52	0.3641 (3)	0.1788 (3)	0.3692 (2)	0.0585 (9)
H52	0.3439	0.2004	0.3211	0.070*
C53	0.2666 (4)	0.1371 (4)	0.4059 (3)	0.0776 (12)
H53	0.1810	0.1313	0.3824	0.093*
C54	0.2936 (4)	0.1043 (3)	0.4756 (2)	0.0666 (10)
H54	0.2268	0.0769	0.4999	0.080*
C55	0.4182 (4)	0.1115 (3)	0.5100 (2)	0.0630 (9)
H55	0.4366	0.0882	0.5576	0.076*
C56	0.5182 (3)	0.1533 (3)	0.4745 (2)	0.0583 (8)
H56	0.6034	0.1578	0.4983	0.070*
C61	0.6926 (3)	0.3802 (2)	0.42251 (17)	0.0446 (7)
C62	0.8032 (3)	0.4444 (3)	0.4071 (2)	0.0597 (9)
H62	0.8394	0.4181	0.3652	0.072*
C63	0.8595 (4)	0.5465 (3)	0.4535 (3)	0.0743 (11)
H63	0.9344	0.5877	0.4434	0.089*
C64	0.8059 (4)	0.5877 (3)	0.5145 (3)	0.0793 (12)
H64	0.8435	0.6570	0.5453	0.095*
C65	0.6963 (4)	0.5260 (3)	0.5297 (2)	0.0742 (11)
H65	0.6595	0.5539	0.5708	0.089*
C66	0.6399 (3)	0.4228 (3)	0.4846 (2)	0.0575 (8)
H66	0.5660	0.3817	0.4960	0.069*
C71	0.7379 (3)	0.1653 (2)	0.37355 (18)	0.0444 (7)
C72	0.7141 (3)	0.0629 (3)	0.3242 (2)	0.0583 (8)
H72	0.6405	0.0402	0.2843	0.070*
C73	0.7991 (4)	−0.0051 (3)	0.3339 (2)	0.0678 (10)
H73	0.7824	−0.0733	0.3005	0.081*
C74	0.9088 (3)	0.0279 (3)	0.3931 (2)	0.0657 (10)
H74	0.9666	−0.0173	0.3993	0.079*
C75	0.9312 (3)	0.1275 (3)	0.4421 (2)	0.0645 (9)
H75	1.0039	0.1494	0.4827	0.077*
C76	0.8469 (3)	0.1965 (3)	0.4323 (2)	0.0558 (8)
H76	0.8643	0.2646	0.4659	0.067*
C1S	−0.0946 (4)	0.2653 (3)	0.6980 (3)	0.0822 (12)
H1S	−0.1093	0.2748	0.7524	0.099*
Cl1S	0.07297 (19)	0.27094 (17)	0.69940 (16)	0.1137 (7)	0.911 (6)
Cl2S	−0.18878 (19)	0.13990 (18)	0.64402 (13)	0.1167 (7)	0.911 (6)
Cl3S	−0.1396 (2)	0.37078 (17)	0.65417 (17)	0.1141 (9)	0.911 (6)
Cl1T	0.0416 (19)	0.2325 (18)	0.7246 (11)	0.094 (6)*	0.089 (6)
Cl2T	−0.162 (2)	0.191 (3)	0.6233 (15)	0.130 (8)*	0.089 (6)
Cl3T	−0.0968 (14)	0.3998 (12)	0.7051 (13)	0.083 (5)*	0.089 (6)
N1S	0.1383 (10)	0.8269 (6)	0.1199 (3)	0.157 (3)
O1S	0.1002 (5)	0.7275 (5)	0.1184 (3)	0.1440 (16)
O2S	0.0559 (12)	0.8453 (8)	0.0668 (6)	0.146 (5)*	0.505 (14)
O2S'	0.1575 (9)	0.9082 (8)	0.0846 (5)	0.123 (4)*	0.495 (14)
O3S	0.2184 (9)	0.8712 (7)	0.1718 (6)	0.182 (4)*	0.719 (12)
O3S'	0.0415 (18)	0.8635 (15)	0.1616 (12)	0.162 (9)*	0.281 (12)
O1W	0.9283 (12)	0.9778 (13)	−0.0008 (10)	0.240 (6)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0457 (2)	0.0458 (2)	0.0419 (2)	0.01544 (16)	0.01346 (16)	0.00713 (15)
P1	0.0477 (4)	0.0513 (4)	0.0405 (4)	0.0202 (3)	0.0129 (3)	0.0096 (3)
P2	0.0363 (4)	0.0465 (4)	0.0409 (4)	0.0123 (3)	0.0109 (3)	0.0093 (3)
N1	0.0652 (17)	0.0463 (14)	0.0434 (15)	0.0186 (13)	0.0071 (13)	0.0042 (11)
C2	0.080 (2)	0.052 (2)	0.059 (2)	0.0102 (18)	0.0028 (19)	0.0029 (16)
C3	0.116 (4)	0.049 (2)	0.074 (3)	0.016 (2)	−0.004 (3)	0.0004 (18)
C4	0.136 (4)	0.068 (3)	0.084 (3)	0.048 (3)	0.018 (3)	−0.006 (2)
C5	0.109 (3)	0.081 (3)	0.065 (3)	0.052 (3)	0.027 (2)	0.003 (2)
C6	0.070 (2)	0.062 (2)	0.0399 (18)	0.0328 (17)	0.0117 (16)	0.0060 (14)
C7	0.0579 (19)	0.070 (2)	0.0459 (19)	0.0287 (17)	0.0176 (15)	0.0137 (15)
C8	0.089 (3)	0.107 (3)	0.067 (3)	0.040 (3)	0.042 (2)	0.022 (2)
C9	0.082 (3)	0.117 (4)	0.090 (3)	0.019 (3)	0.045 (3)	0.041 (3)
C10	0.073 (3)	0.085 (3)	0.097 (3)	0.005 (2)	0.026 (2)	0.044 (3)
C11	0.059 (2)	0.059 (2)	0.069 (2)	0.0074 (17)	0.0163 (18)	0.0153 (17)
N12	0.0491 (14)	0.0550 (15)	0.0500 (16)	0.0185 (12)	0.0147 (12)	0.0125 (12)
C21	0.062 (2)	0.0529 (17)	0.0414 (18)	0.0228 (15)	0.0111 (15)	0.0106 (13)
C22	0.068 (2)	0.101 (3)	0.057 (2)	0.035 (2)	0.0095 (19)	0.023 (2)
C23	0.095 (3)	0.121 (4)	0.052 (3)	0.034 (3)	−0.010 (2)	0.021 (2)
C24	0.128 (4)	0.083 (3)	0.049 (2)	0.035 (3)	0.015 (3)	0.022 (2)
C25	0.105 (3)	0.077 (3)	0.059 (2)	0.023 (2)	0.031 (2)	0.027 (2)
C26	0.071 (2)	0.067 (2)	0.049 (2)	0.0191 (18)	0.0166 (17)	0.0155 (16)
C31	0.0467 (17)	0.063 (2)	0.0479 (19)	0.0194 (15)	0.0093 (14)	0.0190 (15)
C32	0.058 (2)	0.078 (3)	0.066 (2)	0.0139 (19)	0.0105 (18)	0.0127 (19)
C33	0.063 (2)	0.086 (3)	0.091 (3)	−0.003 (2)	0.005 (2)	0.031 (2)
C34	0.053 (2)	0.132 (4)	0.084 (3)	0.020 (3)	0.021 (2)	0.051 (3)
C35	0.071 (3)	0.123 (4)	0.080 (3)	0.044 (3)	0.037 (2)	0.042 (3)
C36	0.061 (2)	0.080 (2)	0.063 (2)	0.0306 (19)	0.0269 (18)	0.0231 (18)
C41	0.0577 (19)	0.0502 (17)	0.0527 (19)	0.0214 (15)	0.0208 (15)	0.0117 (14)
C42	0.079 (3)	0.060 (2)	0.066 (2)	0.0253 (19)	0.006 (2)	−0.0021 (18)
C43	0.106 (4)	0.073 (3)	0.090 (3)	0.025 (3)	0.001 (3)	−0.015 (2)
C44	0.124 (4)	0.058 (2)	0.098 (4)	0.025 (3)	0.036 (3)	−0.002 (2)
C45	0.110 (3)	0.066 (2)	0.091 (3)	0.045 (2)	0.053 (3)	0.031 (2)
C46	0.072 (2)	0.063 (2)	0.063 (2)	0.0302 (18)	0.0256 (18)	0.0188 (17)
C51	0.0431 (15)	0.0408 (15)	0.0455 (17)	0.0129 (12)	0.0112 (13)	0.0100 (12)
C52	0.0426 (17)	0.075 (2)	0.063 (2)	0.0106 (16)	0.0104 (15)	0.0297 (18)
C53	0.0441 (19)	0.102 (3)	0.095 (3)	0.010 (2)	0.022 (2)	0.043 (3)
C54	0.061 (2)	0.067 (2)	0.081 (3)	0.0106 (18)	0.035 (2)	0.0257 (19)
C55	0.077 (3)	0.066 (2)	0.054 (2)	0.0147 (19)	0.0265 (19)	0.0225 (17)
C56	0.0505 (18)	0.075 (2)	0.053 (2)	0.0146 (17)	0.0109 (15)	0.0230 (17)
C61	0.0445 (16)	0.0490 (16)	0.0411 (16)	0.0137 (13)	0.0068 (13)	0.0091 (13)
C62	0.0518 (19)	0.064 (2)	0.059 (2)	0.0031 (16)	0.0134 (16)	0.0092 (16)
C63	0.065 (2)	0.064 (2)	0.081 (3)	−0.0072 (19)	0.009 (2)	0.009 (2)
C64	0.083 (3)	0.056 (2)	0.082 (3)	0.003 (2)	0.001 (2)	−0.003 (2)
C65	0.081 (3)	0.065 (2)	0.071 (3)	0.022 (2)	0.016 (2)	−0.0115 (19)
C66	0.0544 (19)	0.0541 (18)	0.063 (2)	0.0131 (15)	0.0170 (16)	0.0014 (15)
C71	0.0399 (15)	0.0529 (17)	0.0478 (18)	0.0174 (13)	0.0156 (13)	0.0164 (13)
C72	0.0558 (19)	0.0559 (19)	0.065 (2)	0.0204 (16)	0.0077 (17)	0.0125 (16)
C73	0.079 (3)	0.056 (2)	0.078 (3)	0.0294 (19)	0.022 (2)	0.0162 (18)
C74	0.055 (2)	0.071 (2)	0.093 (3)	0.0326 (18)	0.030 (2)	0.041 (2)
C75	0.0427 (18)	0.080 (3)	0.079 (3)	0.0223 (17)	0.0105 (17)	0.030 (2)
C76	0.0440 (17)	0.064 (2)	0.061 (2)	0.0180 (15)	0.0082 (15)	0.0113 (16)
C1S	0.106 (3)	0.072 (3)	0.070 (3)	0.032 (2)	0.015 (2)	0.008 (2)
Cl1S	0.1039 (12)	0.0881 (11)	0.1527 (17)	0.0357 (9)	0.0224 (11)	0.0201 (11)
Cl2S	0.1263 (13)	0.0855 (12)	0.1194 (14)	0.0151 (10)	0.0038 (10)	−0.0035 (10)
Cl3S	0.1557 (17)	0.1091 (12)	0.123 (2)	0.0812 (12)	0.0695 (16)	0.0501 (12)
N1S	0.281 (9)	0.163 (6)	0.063 (3)	0.120 (6)	0.025 (5)	0.049 (4)
O1S	0.138 (4)	0.184 (5)	0.110 (3)	0.059 (4)	0.013 (3)	0.012 (3)

Geometric parameters (Å, º) top

Cu1—N1	2.070 (2)	C42—C43	1.381 (5)
Cu1—N12	2.103 (3)	C42—H42	0.9300
Cu1—P2	2.2600 (9)	C43—C44	1.370 (7)
Cu1—P1	2.2659 (9)	C43—H43	0.9300
P1—C21	1.824 (3)	C44—C45	1.373 (6)
P1—C31	1.825 (3)	C44—H44	0.9300
P1—C41	1.828 (3)	C45—C46	1.383 (5)
P2—C51	1.821 (3)	C45—H45	0.9300
P2—C61	1.825 (3)	C46—H46	0.9300
P2—C71	1.839 (3)	C51—C52	1.382 (4)
N1—C2	1.341 (4)	C51—C56	1.382 (4)
N1—C6	1.347 (4)	C52—C53	1.377 (5)
C2—C3	1.395 (5)	C52—H52	0.9300
C2—H2	0.9300	C53—C54	1.353 (5)
C3—C4	1.356 (7)	C53—H53	0.9300
C3—H3	0.9300	C54—C55	1.357 (5)
C4—C5	1.370 (6)	C54—H54	0.9300
C4—H4	0.9300	C55—C56	1.385 (5)
C5—C6	1.393 (5)	C55—H55	0.9300
C5—H5	0.9300	C56—H56	0.9300
C6—C7	1.483 (5)	C61—C66	1.386 (4)
C7—N12	1.345 (4)	C61—C62	1.394 (4)
C7—C8	1.396 (5)	C62—C63	1.379 (5)
C8—C9	1.357 (6)	C62—H62	0.9300
C8—H8	0.9300	C63—C64	1.371 (6)
C9—C10	1.362 (7)	C63—H63	0.9300
C9—H9	0.9300	C64—C65	1.370 (6)
C10—C11	1.382 (5)	C64—H64	0.9300
C10—H10	0.9300	C65—C66	1.382 (5)
C11—N12	1.349 (4)	C65—H65	0.9300
C11—H11	0.9300	C66—H66	0.9300
C21—C22	1.384 (5)	C71—C76	1.373 (4)
C21—C26	1.388 (5)	C71—C72	1.392 (4)
C22—C23	1.389 (5)	C72—C73	1.382 (5)
C22—H22	0.9300	C72—H72	0.9300
C23—C24	1.347 (6)	C73—C74	1.383 (5)
C23—H23	0.9300	C73—H73	0.9300
C24—C25	1.355 (6)	C74—C75	1.363 (5)
C24—H24	0.9300	C74—H74	0.9300
C25—C26	1.378 (5)	C75—C76	1.386 (5)
C25—H25	0.9300	C75—H75	0.9300
C26—H26	0.9300	C76—H76	0.9300
C31—C32	1.382 (5)	C1S—H1S	0.9800
C31—C36	1.384 (5)	C1S—Cl1S	1.786 (5)
C32—C33	1.398 (5)	C1S—Cl2S	1.741 (4)
C32—H32	0.9300	C1S—Cl3S	1.750 (4)
C33—C34	1.371 (6)	C1S—Cl1t	1.617 (19)
C33—H33	0.9300	C1S—Cl2t	1.47 (3)
C34—C35	1.363 (6)	C1S—Cl3t	1.694 (15)
C34—H34	0.9300	N1S—O3S	1.131 (10)
C35—C36	1.382 (5)	N1S—O1S	1.241 (8)
C35—H35	0.9300	N1S—O2S	1.259 (12)
C36—H36	0.9300	N1S—O2S'	1.282 (10)
C41—C42	1.382 (5)	N1S—O3S'	1.47 (2)
C41—C46	1.394 (5)

N1—Cu1—N12	79.71 (10)	C42—C41—C46	118.5 (3)
N1—Cu1—P2	111.18 (8)	C42—C41—P1	119.2 (3)
N12—Cu1—P2	111.86 (7)	C46—C41—P1	122.2 (3)
N1—Cu1—P1	111.46 (8)	C43—C42—C41	121.0 (4)
N12—Cu1—P1	108.68 (7)	C43—C42—H42	119.5
P2—Cu1—P1	124.89 (3)	C41—C42—H42	119.5
C21—P1—C31	104.14 (15)	C44—C43—C42	119.4 (4)
C21—P1—C41	102.77 (14)	C44—C43—H43	120.3
C31—P1—C41	104.43 (15)	C42—C43—H43	120.3
C21—P1—Cu1	114.07 (11)	C43—C44—C45	121.1 (4)
C31—P1—Cu1	115.68 (10)	C43—C44—H44	119.5
C41—P1—Cu1	114.29 (11)	C45—C44—H44	119.5
C51—P2—C61	103.12 (13)	C44—C45—C46	119.4 (4)
C51—P2—C71	101.93 (13)	C44—C45—H45	120.3
C61—P2—C71	103.69 (14)	C46—C45—H45	120.3
C51—P2—Cu1	118.06 (10)	C45—C46—C41	120.5 (4)
C61—P2—Cu1	112.74 (10)	C45—C46—H46	119.7
C71—P2—Cu1	115.48 (10)	C41—C46—H46	119.7
C2—N1—C6	118.3 (3)	C52—C51—C56	118.5 (3)
C2—N1—Cu1	127.0 (2)	C52—C51—P2	118.9 (2)
C6—N1—Cu1	113.9 (2)	C56—C51—P2	122.6 (2)
N1—C2—C3	122.1 (4)	C53—C52—C51	120.0 (3)
N1—C2—H2	118.9	C53—C52—H52	120.0
C3—C2—H2	118.9	C51—C52—H52	120.0
C4—C3—C2	118.7 (4)	C54—C53—C52	121.0 (4)
C4—C3—H3	120.6	C54—C53—H53	119.5
C2—C3—H3	120.6	C52—C53—H53	119.5
C3—C4—C5	120.3 (4)	C53—C54—C55	119.9 (3)
C3—C4—H4	119.8	C53—C54—H54	120.0
C5—C4—H4	119.8	C55—C54—H54	120.0
C4—C5—C6	118.7 (4)	C54—C55—C56	120.3 (3)
C4—C5—H5	120.7	C54—C55—H55	119.8
C6—C5—H5	120.7	C56—C55—H55	119.8
N1—C6—C5	121.8 (3)	C51—C56—C55	120.2 (3)
N1—C6—C7	116.0 (3)	C51—C56—H56	119.9
C5—C6—C7	122.2 (3)	C55—C56—H56	119.9
N12—C7—C8	121.4 (3)	C66—C61—C62	118.1 (3)
N12—C7—C6	115.8 (3)	C66—C61—P2	123.4 (2)
C8—C7—C6	122.7 (3)	C62—C61—P2	118.4 (2)
C9—C8—C7	119.6 (4)	C63—C62—C61	120.7 (3)
C9—C8—H8	120.2	C63—C62—H62	119.7
C7—C8—H8	120.2	C61—C62—H62	119.7
C8—C9—C10	119.7 (4)	C64—C63—C62	120.5 (4)
C8—C9—H9	120.1	C64—C63—H63	119.7
C10—C9—H9	120.1	C62—C63—H63	119.7
C9—C10—C11	118.8 (4)	C65—C64—C63	119.4 (3)
C9—C10—H10	120.6	C65—C64—H64	120.3
C11—C10—H10	120.6	C63—C64—H64	120.3
N12—C11—C10	122.7 (4)	C64—C65—C66	120.8 (4)
N12—C11—H11	118.6	C64—C65—H65	119.6
C10—C11—H11	118.6	C66—C65—H65	119.6
C7—N12—C11	117.7 (3)	C65—C66—C61	120.5 (3)
C7—N12—Cu1	113.2 (2)	C65—C66—H66	119.8
C11—N12—Cu1	128.0 (2)	C61—C66—H66	119.8
C22—C21—C26	117.8 (3)	C76—C71—C72	118.5 (3)
C22—C21—P1	125.0 (3)	C76—C71—P2	124.5 (2)
C26—C21—P1	117.2 (3)	C72—C71—P2	117.0 (2)
C21—C22—C23	119.7 (4)	C73—C72—C71	120.5 (3)
C21—C22—H22	120.1	C73—C72—H72	119.7
C23—C22—H22	120.1	C71—C72—H72	119.7
C24—C23—C22	121.3 (4)	C72—C73—C74	120.2 (4)
C24—C23—H23	119.3	C72—C73—H73	119.9
C22—C23—H23	119.3	C74—C73—H73	119.9
C23—C24—C25	119.8 (4)	C75—C74—C73	119.3 (3)
C23—C24—H24	120.1	C75—C74—H74	120.3
C25—C24—H24	120.1	C73—C74—H74	120.3
C24—C25—C26	120.3 (4)	C74—C75—C76	120.8 (3)
C24—C25—H25	119.9	C74—C75—H75	119.6
C26—C25—H25	119.9	C76—C75—H75	119.6
C25—C26—C21	121.0 (4)	C71—C76—C75	120.7 (3)
C25—C26—H26	119.5	C71—C76—H76	119.7
C21—C26—H26	119.5	C75—C76—H76	119.7
C32—C31—C36	118.8 (3)	Cl2S—C1S—Cl1S	110.6 (2)
C32—C31—P1	118.3 (3)	Cl2S—C1S—Cl3S	109.0 (3)
C36—C31—P1	122.7 (3)	Cl3S—C1S—Cl1S	109.3 (3)
C31—C32—C33	120.4 (4)	Cl1S—C1S—H1S	109.3
C31—C32—H32	119.8	Cl2S—C1S—H1S	109.3
C33—C32—H32	119.8	Cl3S—C1S—H1S	109.3
C34—C33—C32	119.6 (4)	Cl2t—C1S—Cl1t	107.6 (12)
C34—C33—H33	120.2	Cl2t—C1S—Cl3t	117.1 (11)
C32—C33—H33	120.2	Cl3t—C1S—Cl1t	118.8 (9)
C35—C34—C33	120.2 (4)	Cl1t—C1S—H1S	91.7
C35—C34—H34	119.9	Cl2t—C1S—H1S	134.5
C33—C34—H34	119.9	Cl3t—C1S—H1S	85.6
C34—C35—C36	120.6 (4)	O3S—N1S—O1S	114.4 (7)
C34—C35—H35	119.7	O3S—N1S—O2S	141.2 (10)
C36—C35—H35	119.7	O1S—N1S—O2S	103.1 (9)
C35—C36—C31	120.4 (4)	O1S—N1S—O2S'	151.1 (7)
C35—C36—H36	119.8	O1S—N1S—O3S'	96.4 (10)
C31—C36—H36	119.8	O2S'—N1S—O3S'	96.0 (9)

N1—Cu1—P1—C21	−37.02 (14)	C21—P1—C31—C32	67.5 (3)
N12—Cu1—P1—C21	48.98 (14)	C41—P1—C31—C32	175.0 (3)
P2—Cu1—P1—C21	−175.39 (11)	Cu1—P1—C31—C32	−58.5 (3)
N1—Cu1—P1—C31	83.75 (15)	C21—P1—C31—C36	−117.3 (3)
N12—Cu1—P1—C31	169.75 (14)	C41—P1—C31—C36	−9.8 (3)
P2—Cu1—P1—C31	−54.62 (13)	Cu1—P1—C31—C36	116.7 (3)
N1—Cu1—P1—C41	−154.89 (14)	C36—C31—C32—C33	−0.5 (5)
N12—Cu1—P1—C41	−68.88 (14)	P1—C31—C32—C33	174.9 (3)
P2—Cu1—P1—C41	66.75 (12)	C31—C32—C33—C34	0.1 (6)
N1—Cu1—P2—C51	−87.33 (13)	C32—C33—C34—C35	0.4 (6)
N12—Cu1—P2—C51	−174.41 (13)	C33—C34—C35—C36	−0.5 (7)
P1—Cu1—P2—C51	51.13 (11)	C34—C35—C36—C31	0.2 (6)
N1—Cu1—P2—C61	152.51 (14)	C32—C31—C36—C35	0.3 (5)
N12—Cu1—P2—C61	65.43 (13)	P1—C31—C36—C35	−174.8 (3)
P1—Cu1—P2—C61	−69.03 (11)	C21—P1—C41—C42	−140.2 (3)
N1—Cu1—P2—C71	33.56 (14)	C31—P1—C41—C42	111.3 (3)
N12—Cu1—P2—C71	−53.51 (13)	Cu1—P1—C41—C42	−16.1 (3)
P1—Cu1—P2—C71	172.03 (11)	C21—P1—C41—C46	39.2 (3)
N12—Cu1—N1—C2	174.9 (3)	C31—P1—C41—C46	−69.3 (3)
P2—Cu1—N1—C2	65.3 (3)	Cu1—P1—C41—C46	163.3 (2)
P1—Cu1—N1—C2	−79.0 (3)	C46—C41—C42—C43	0.2 (6)
N12—Cu1—N1—C6	5.6 (2)	P1—C41—C42—C43	179.6 (3)
P2—Cu1—N1—C6	−104.0 (2)	C41—C42—C43—C44	−0.8 (7)
P1—Cu1—N1—C6	111.7 (2)	C42—C43—C44—C45	1.3 (8)
C6—N1—C2—C3	1.6 (5)	C43—C44—C45—C46	−1.2 (7)
Cu1—N1—C2—C3	−167.3 (3)	C44—C45—C46—C41	0.6 (6)
N1—C2—C3—C4	0.0 (6)	C42—C41—C46—C45	−0.2 (5)
C2—C3—C4—C5	−0.8 (7)	P1—C41—C46—C45	−179.6 (3)
C3—C4—C5—C6	0.2 (7)	C61—P2—C51—C52	110.3 (3)
C2—N1—C6—C5	−2.3 (5)	C71—P2—C51—C52	−142.3 (3)
Cu1—N1—C6—C5	168.0 (3)	Cu1—P2—C51—C52	−14.7 (3)
C2—N1—C6—C7	177.7 (3)	C61—P2—C51—C56	−68.6 (3)
Cu1—N1—C6—C7	−12.0 (3)	C71—P2—C51—C56	38.8 (3)
C4—C5—C6—N1	1.4 (6)	Cu1—P2—C51—C56	166.4 (2)
C4—C5—C6—C7	−178.5 (4)	C56—C51—C52—C53	1.4 (5)
N1—C6—C7—N12	14.2 (4)	P2—C51—C52—C53	−177.6 (3)
C5—C6—C7—N12	−165.8 (3)	C51—C52—C53—C54	−0.5 (6)
N1—C6—C7—C8	−161.7 (3)	C52—C53—C54—C55	−0.6 (6)
C5—C6—C7—C8	18.3 (5)	C53—C54—C55—C56	0.7 (6)
N12—C7—C8—C9	1.2 (6)	C52—C51—C56—C55	−1.2 (5)
C6—C7—C8—C9	176.8 (4)	P2—C51—C56—C55	177.7 (3)
C7—C8—C9—C10	−0.5 (7)	C54—C55—C56—C51	0.2 (6)
C8—C9—C10—C11	0.6 (7)	C51—P2—C61—C66	−10.6 (3)
C9—C10—C11—N12	−1.4 (6)	C71—P2—C61—C66	−116.6 (3)
C8—C7—N12—C11	−1.9 (5)	Cu1—P2—C61—C66	117.8 (3)
C6—C7—N12—C11	−177.9 (3)	C51—P2—C61—C62	173.9 (3)
C8—C7—N12—Cu1	167.0 (3)	C71—P2—C61—C62	67.9 (3)
C6—C7—N12—Cu1	−9.0 (4)	Cu1—P2—C61—C62	−57.7 (3)
C10—C11—N12—C7	2.0 (5)	C66—C61—C62—C63	1.2 (5)
C10—C11—N12—Cu1	−164.9 (3)	P2—C61—C62—C63	176.9 (3)
N1—Cu1—N12—C7	2.2 (2)	C61—C62—C63—C64	−1.5 (6)
P2—Cu1—N12—C7	111.0 (2)	C62—C63—C64—C65	0.8 (7)
P1—Cu1—N12—C7	−107.2 (2)	C63—C64—C65—C66	0.3 (7)
N1—Cu1—N12—C11	169.6 (3)	C64—C65—C66—C61	−0.6 (6)
P2—Cu1—N12—C11	−81.5 (3)	C62—C61—C66—C65	−0.1 (5)
P1—Cu1—N12—C11	60.3 (3)	P2—C61—C66—C65	−175.6 (3)
C31—P1—C21—C22	9.1 (3)	C51—P2—C71—C76	−99.3 (3)
C41—P1—C21—C22	−99.6 (3)	C61—P2—C71—C76	7.6 (3)
Cu1—P1—C21—C22	136.1 (3)	Cu1—P2—C71—C76	131.4 (2)
C31—P1—C21—C26	−171.6 (3)	C51—P2—C71—C72	79.9 (3)
C41—P1—C21—C26	79.7 (3)	C61—P2—C71—C72	−173.2 (2)
Cu1—P1—C21—C26	−44.6 (3)	Cu1—P2—C71—C72	−49.4 (3)
C26—C21—C22—C23	−0.1 (6)	C76—C71—C72—C73	−0.5 (5)
P1—C21—C22—C23	179.1 (3)	P2—C71—C72—C73	−179.8 (3)
C21—C22—C23—C24	−1.4 (7)	C71—C72—C73—C74	0.1 (5)
C22—C23—C24—C25	1.9 (7)	C72—C73—C74—C75	0.8 (6)
C23—C24—C25—C26	−0.8 (7)	C73—C74—C75—C76	−1.3 (5)
C24—C25—C26—C21	−0.7 (6)	C72—C71—C76—C75	0.0 (5)
C22—C21—C26—C25	1.1 (5)	P2—C71—C76—C75	179.2 (3)
P1—C21—C26—C25	−178.2 (3)	C74—C75—C76—C71	0.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3Sⁱ	0.93	2.56	3.317 (9)	139
C5—H5···O1Wⁱ	0.93	2.34	3.182 (15)	151
C8—H8···O2Sⁱⁱ	0.93	2.38	3.242 (11)	155
C45—H45···O3S	0.93	2.59	3.493 (10)	163
C1S—H1S···O1Sⁱⁱⁱ	0.98	2.25	3.204 (7)	165
O1W···O2S^iv	?	?	2.663 (19)	?
O1W···O2S^v	?	?	2.667 (19)	?

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₈N₂)(C₁₈H₁₅P)₂]NO₃·CHCl₃·0.5H₂O
M_r	934.65
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.754 (2), 12.672 (3), 17.464 (4)
α, β, γ (°)	99.100 (5), 99.279 (4), 101.229 (5)
V (Å³)	2259.4 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.56 × 0.51 × 0.40

Data collection
Diffractometer	Rigaku AFC7S Mercury diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.584, 0.733
No. of measured, independent and observed [I > 2σ(I)] reflections	25842, 8576, 6719
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.136, 1.06
No. of reflections	8576
No. of parameters	549
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.53

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Cu1—N1	2.070 (2)	Cu1—P2	2.2600 (9)
Cu1—N12	2.103 (3)	Cu1—P1	2.2659 (9)

N1—Cu1—N12	79.71 (10)	N1—Cu1—P1	111.46 (8)
N1—Cu1—P2	111.18 (8)	N12—Cu1—P1	108.68 (7)
N12—Cu1—P2	111.86 (7)	P2—Cu1—P1	124.89 (3)

N1—C6—C7—N12	14.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3Sⁱ	0.93	2.56	3.317 (9)	139.1
C5—H5···O1Wⁱ	0.93	2.34	3.182 (15)	150.6
C8—H8···O2Sⁱⁱ	0.93	2.38	3.242 (11)	154.7
C45—H45···O3S	0.93	2.59	3.493 (10)	162.6
C1S—H1S···O1Sⁱⁱⁱ	0.98	2.25	3.204 (7)	164.6
O1W···O2S^iv	?	?	2.663 (19)	?
O1W···O2S^v	?	?	2.667 (19)	?

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

Acknowledgements

Financial support from the Fondo Nacional de Ciencia, Tecnología e Investigación (FONACIT) of Venezuela, project Lab-199700821, is gratefully acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Engelhardt, L. M., Pakawatchai, C., White, A. H. & Healy, P. C. (1985). J. Chem. Soc. Dalton Trans. pp. 125–133. CSD CrossRef Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hirshfeld, F. L. (1976). Acta Cryst. A32, 239–244. CrossRef IUCr Journals Web of Science Google Scholar
Navarro, M., Cisneros-Fajardo, E., Fernandez-Mestre, M., Arriechi, D. & Marchan, E. (2003). J. Inorg. Biochem. 97, 364–369. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13 Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 4| April 2008| Pages m533-m534

doi:10.1107/S1600536808006260

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2,2′-Bi­pyridine)bis­­(tri­phenyl­phosphine)copper(I) nitrate chloro­form solvate hemihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(2,2′-Bipyridine)bis(triphenylphosphine)copper(I) nitrate chloroform solvate hemihydrate