Iodidotris(triphenyl­phosphine)copper(I) acetonitrile solvate

Venkatraman, R.; Fronczek, F.R.

doi:10.1107/S1600536808007174

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m577

doi:10.1107/S1600536808007174

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Iodidotris(triphenylphosphine)copper(I) acetonitrile solvate

Ramaiyer Venkatraman ^a and Frank R. Fronczek ^b ^*

^aDepartment of Chemistry, Jackson State University, Jackson, MS 39217, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 22 November 2007; accepted 15 March 2008; online 29 March 2008)

The title compound, [CuI(C₁₈H₁₅P)₃]·C₂H₃N, was obtained from the reaction of triphenylphosphine and copper(I) iodide in acetonitrile. The monomeric form of the complex has slightly distorted coordination of Cu by the I atom and three P atoms. The crystal structure is stabilized by C—H⋯π interactions between phenyl H atoms and phenyl rings. In addition, the complex molecules exhibit C—H⋯N hydrogen bonds between phenyl H atoms and acetonitrile N atoms. The crystal used was an inversion twin, with nearly equal component populations of 0.522 (8) and 0.478 (8).

Related literature

For details of the crystal structures of organophosphinecopper(I) halide derivatives, see: Caulton et al. (1990 ); Bowmaker et al. (2000 ); Eller et al. (1977 ); Hamel et al. (2002 ); Hanna et al. (2005 ); Venkatraman et al. (2006 ); Barron et al. (1987 ); Kräuter & Newmüller (1996 ).

Experimental

Crystal data

[CuI(C₁₈H₁₅P)₃]·C₂H₃N
M_r = 1018.30
Orthorhombic, P n a 2₁
a = 18.5726 (10) Å
b = 20.2631 (12) Å
c = 12.7839 (5) Å
V = 4811.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 115 (2) K
0.30 × 0.25 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.709, T_max = 0.818
156685 measured reflections
15969 independent reflections
13488 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.068
S = 1.03
15969 reflections
561 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.66 e Å⁻³
Absolute structure: Flack (1983 ), 7443 Friedel pairs
Flack parameter: 0.478 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg1ⁱ	0.95	2.94	3.732	141
C40—H40⋯Cg2ⁱ	0.95	2.94	3.696	137
C39—H39⋯N1Sⁱⁱ	0.95	2.58	3.468 (4)	157
Symmetry codes: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1. Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007174/lx2043sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007174/lx2043Isup2.hkl

checkCIF report

Comment top

Organophosphinecopper (I) halides have widely investigated system due to the formation of varying types of crystal structures (Caulton et al., 1990). Eller et al. (1977) used the organophosphinecopper (I) systems for the direct Cu–SO₂ adduct formation. Recently Hanna et al. (2005) reported the structural and solid state NMR studies of the four coordinate copper (I) complexes with different cations except iodide. During our study on the interaction of heterocyclic thiosemicarbazones with copper (I) halides, we were able to isolate the title compound (1), Venkatraman et al., (2006).

The structure consists of CuI(PPh₃)₃ unit similar to the structure described by Eller et al. (1977) for CuI(PPh₂Me)₃. The asymmetric unit of (1) contains one formula unit of the complex with no crystallographically imposed symmetry (Fig.1), and one acetonitrile solvent molecule. The Cu atom is surrounded by three phosphorus atoms and the iodide atom in a distorted tetrahedral geometry. The three independent Cu—P distances are not grossly different (2.3421 (6), 2.3463 (6), and 2.3295 (7) Å) for P1, P2, and P3, respectively, and the Cu—I distance is 2.6843 (3) Å. The Cu—P bond lengths in compound (1) are similar to values recorded for a range of other [Cu-(PPh3)₃X] complexes [Bowmaker et al., (2000)]. The three P—Cu—I angles are 104.75 (2), 113.66 (2), and 97.69 (2)°, for P1, P2, and P3, respectively, [average 105.2°], and sums to 316.0°. The wide range of P—Cu—P/I angles indicate an irregular tetrahedral structure.

The molecular packing (Fig. 2) is stabilized by CH₂—H···π interactions between the hydrogen of phenyl group and the phenyl ring, with C9—H9···Cg1ⁱ and C40—H40···Cg2ⁱ separations of 2.94 Å (Fig. 2 & Table 1) (Cg1 and Cg2 are the centroids of C1—C6 and C7—C12 phenyl rings, respectively). Further stability comes from weak C—H···N1Sⁱⁱ hydrogen bond in Fig. 2 and Table 1. A l l symmetry codes as in Table 1.

Related literature top

For the details of crystal structure of organophosphinecopper(I) halide derivatives, see: Caulton et al., (1990); Bowmaker et al., (2000); Eller et al. (1977); Hamel et al. (2002); Hanna et al. (2005); Venkatraman et al., (2006); Barron et al. (1987); Kräuter & Newmüller (1996).

Experimental top

To a solution of copper (I) iodide (Aldrich; 0.190 g, 1 mmol) in acetonitrile (Aldrich; 50 ml) was added solid triphenylphosphine (Aldrich; 0.262 g, 2 mmol) in presence 0.5 ml HCl. The resulting mixture was stirred overnight. The clear solution was filtered and allowed to evaporate at room temperature in the presence of air. A colorless crystalline product suitable for X-ray diffraction was formed (yield ca 70%).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Numbering scheme and ellipsoids at the 50% level. H atoms are not shown.
	Fig. 2. C—H···N and C—H···π interactions. Geometric parameters and symmetry operations are given in the Table 1.

Iodidotris(triphenylphosphine)copper(I) acetonitrile solvate top

Crystal data top

[CuI(C₁₈H₁₅P)₃]·C₂H₃N	F(000) = 2072
M_r = 1018.30	D_x = 1.406 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8935 reflections
a = 18.573 (1) Å	θ = 2.5–31.8°
b = 20.263 (1) Å	µ = 1.23 mm⁻¹
c = 12.7839 (5) Å	T = 115 K
V = 4811.2 (4) Å³	Fragment, colorless
Z = 4	0.30 × 0.25 × 0.17 mm

Data collection top

Nonius KappaCCD diffractometer (with an Oxford Cryosystems Cryostream cooler)	15969 independent reflections
Radiation source: fine-focus sealed tube	13488 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ω scans with κ offsets	θ_max = 31.8°, θ_min = 2.8°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −27→27
T_min = 0.709, T_max = 0.818	k = −29→30
156685 measured reflections	l = −18→18

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-atom parameters constrained
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0253P)² + 3.4731P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
15969 reflections	Δρ_max = 0.62 e Å⁻³
561 parameters	Δρ_min = −0.66 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.478 (8)

Crystal data top

[CuI(C₁₈H₁₅P)₃]·C₂H₃N	V = 4811.2 (4) Å³
M_r = 1018.30	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 18.573 (1) Å	µ = 1.23 mm⁻¹
b = 20.263 (1) Å	T = 115 K
c = 12.7839 (5) Å	0.30 × 0.25 × 0.17 mm

Data collection top

Nonius KappaCCD diffractometer (with an Oxford Cryosystems Cryostream cooler)	15969 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	13488 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.818	R_int = 0.000
156685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.62 e Å⁻³
S = 1.03	Δρ_min = −0.66 e Å⁻³
15969 reflections	Absolute structure: Flack (1983)
561 parameters	Absolute structure parameter: 0.478 (8)
1 restraint

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
I	0.217564 (7)	0.266851 (6)	0.441186 (16)	0.02077 (3)
Cu	0.240945 (12)	0.397554 (11)	0.44517 (3)	0.01359 (5)
P1	0.13455 (3)	0.44254 (3)	0.51291 (5)	0.01432 (10)
P2	0.33677 (3)	0.42893 (3)	0.55393 (5)	0.01575 (11)
P3	0.25929 (3)	0.41255 (3)	0.26648 (4)	0.01450 (10)
C1	0.13962 (12)	0.45371 (12)	0.65502 (18)	0.0178 (4)
C2	0.12435 (12)	0.51230 (12)	0.70821 (19)	0.0207 (5)
H2	0.1108	0.5506	0.6700	0.025*
C3	0.12884 (14)	0.51494 (14)	0.8170 (2)	0.0273 (6)
H3	0.1185	0.5549	0.8527	0.033*
C4	0.14844 (14)	0.45912 (16)	0.8732 (2)	0.0301 (6)
H4	0.1513	0.4609	0.9473	0.036*
C5	0.16373 (14)	0.40114 (15)	0.8213 (2)	0.0283 (6)
H5	0.1773	0.3630	0.8598	0.034*
C6	0.15930 (14)	0.39828 (13)	0.7130 (2)	0.0217 (5)
H6	0.1698	0.3581	0.6779	0.026*
C7	0.11119 (12)	0.52434 (11)	0.46264 (16)	0.0175 (5)
C8	0.05030 (12)	0.53500 (12)	0.40169 (18)	0.0191 (4)
H8	0.0173	0.4999	0.3900	0.023*
C9	0.03727 (13)	0.59699 (13)	0.3575 (2)	0.0228 (5)
H9	−0.0040	0.6036	0.3148	0.027*
C10	0.08404 (14)	0.64869 (13)	0.3755 (2)	0.0249 (5)
H10	0.0749	0.6908	0.3455	0.030*
C11	0.14434 (11)	0.63916 (10)	0.4375 (3)	0.0234 (4)
H11	0.1760	0.6750	0.4509	0.028*
C12	0.15866 (13)	0.57737 (12)	0.48005 (19)	0.0205 (5)
H12	0.2007	0.5709	0.5211	0.025*
C13	0.04853 (12)	0.39823 (11)	0.50234 (19)	0.0186 (4)
C14	0.03752 (13)	0.35252 (12)	0.4235 (2)	0.0268 (6)
H14	0.0753	0.3423	0.3762	0.032*
C15	−0.02950 (15)	0.32139 (13)	0.4135 (2)	0.0336 (7)
H15	−0.0372	0.2908	0.3584	0.040*
C16	−0.08436 (15)	0.33469 (14)	0.4829 (3)	0.0360 (7)
H16	−0.1295	0.3130	0.4758	0.043*
C17	−0.07363 (14)	0.37963 (15)	0.5628 (2)	0.0337 (6)
H17	−0.1112	0.3885	0.6113	0.040*
C18	−0.00801 (13)	0.41170 (14)	0.5719 (2)	0.0256 (5)
H18	−0.0012	0.4432	0.6261	0.031*
C19	0.42750 (12)	0.41851 (12)	0.49989 (19)	0.0196 (5)
C20	0.48602 (14)	0.45677 (13)	0.5321 (2)	0.0300 (6)
H20	0.4792	0.4912	0.5816	0.036*
C21	0.55453 (14)	0.44453 (15)	0.4916 (3)	0.0359 (7)
H21	0.5939	0.4715	0.5121	0.043*
C22	0.56534 (14)	0.39352 (14)	0.4220 (2)	0.0314 (7)
H22	0.6121	0.3852	0.3950	0.038*
C23	0.50823 (15)	0.35457 (15)	0.3917 (2)	0.0293 (6)
H23	0.5159	0.3191	0.3445	0.035*
C24	0.43900 (12)	0.36709 (12)	0.4301 (2)	0.0230 (5)
H24	0.3998	0.3403	0.4084	0.028*
C25	0.33421 (12)	0.51645 (11)	0.59215 (19)	0.0176 (4)
C26	0.29808 (12)	0.53569 (12)	0.6835 (2)	0.0205 (5)
H26	0.2781	0.5032	0.7284	0.025*
C27	0.29136 (14)	0.60257 (14)	0.7087 (2)	0.0266 (6)
H27	0.2668	0.6153	0.7706	0.032*
C28	0.32047 (15)	0.65019 (13)	0.6435 (2)	0.0313 (6)
H28	0.3166	0.6955	0.6615	0.038*
C29	0.35523 (14)	0.63185 (13)	0.5523 (2)	0.0297 (6)
H29	0.3743	0.6647	0.5070	0.036*
C30	0.36235 (13)	0.56523 (12)	0.5268 (2)	0.0226 (5)
H30	0.3866	0.5529	0.4643	0.027*
C31	0.34799 (14)	0.38716 (13)	0.6806 (2)	0.0192 (5)
C32	0.31740 (14)	0.32518 (13)	0.6941 (2)	0.0232 (5)
H32	0.2918	0.3052	0.6381	0.028*
C33	0.32387 (16)	0.29223 (14)	0.7889 (2)	0.0319 (6)
H33	0.3025	0.2500	0.7977	0.038*
C34	0.36150 (18)	0.32092 (15)	0.8706 (2)	0.0377 (7)
H34	0.3649	0.2989	0.9361	0.045*
C35	0.39419 (18)	0.38161 (14)	0.8570 (2)	0.0372 (7)
H35	0.4210	0.4008	0.9125	0.045*
C36	0.38781 (16)	0.41478 (14)	0.7618 (2)	0.0302 (6)
H36	0.4107	0.4563	0.7524	0.036*
C37	0.18119 (13)	0.38725 (13)	0.18883 (19)	0.0193 (5)
C38	0.18054 (15)	0.33782 (12)	0.1132 (2)	0.0261 (5)
H38	0.2234	0.3143	0.0971	0.031*
C39	0.11603 (19)	0.32291 (14)	0.0607 (2)	0.0367 (7)
H39	0.1155	0.2893	0.0089	0.044*
C40	0.05379 (17)	0.35655 (16)	0.0839 (3)	0.0403 (8)
H40	0.0102	0.3453	0.0492	0.048*
C41	0.05425 (16)	0.40674 (18)	0.1574 (3)	0.0413 (8)
H41	0.0114	0.4305	0.1726	0.050*
C42	0.11817 (14)	0.42195 (16)	0.2089 (2)	0.0303 (6)
H42	0.1187	0.4567	0.2587	0.036*
C43	0.26948 (12)	0.49703 (12)	0.21873 (19)	0.0182 (4)
C44	0.28124 (15)	0.54660 (13)	0.2903 (2)	0.0262 (5)
H44	0.2849	0.5360	0.3625	0.031*
C45	0.28790 (17)	0.61243 (14)	0.2582 (3)	0.0380 (7)
H45	0.2969	0.6462	0.3081	0.046*
C46	0.28136 (16)	0.62768 (15)	0.1545 (3)	0.0367 (7)
H46	0.2858	0.6723	0.1325	0.044*
C47	0.26847 (14)	0.57923 (15)	0.0817 (2)	0.0320 (6)
H47	0.2632	0.5906	0.0100	0.038*
C48	0.26316 (14)	0.51345 (14)	0.1126 (2)	0.0253 (5)
H48	0.2553	0.4799	0.0620	0.030*
C49	0.33584 (14)	0.36919 (13)	0.20742 (19)	0.0182 (5)
C50	0.33779 (14)	0.30007 (13)	0.2073 (2)	0.0228 (5)
H50	0.2983	0.2759	0.2350	0.027*
C51	0.39711 (15)	0.26645 (13)	0.1669 (2)	0.0260 (5)
H51	0.3976	0.2196	0.1663	0.031*
C52	0.45517 (15)	0.30119 (15)	0.1277 (2)	0.0299 (6)
H52	0.4953	0.2783	0.0994	0.036*
C53	0.45462 (15)	0.36930 (15)	0.1297 (2)	0.0299 (6)
H53	0.4950	0.3932	0.1042	0.036*
C54	0.39532 (13)	0.40330 (13)	0.1690 (2)	0.0218 (5)
H54	0.3955	0.4502	0.1696	0.026*
N1S	0.0790 (2)	0.23273 (17)	0.8365 (3)	0.0715 (12)
C1S	0.05774 (19)	0.22818 (15)	0.7540 (3)	0.0409 (7)
C2S	0.0311 (2)	0.22160 (19)	0.6481 (3)	0.0474 (8)
H21S	0.0714	0.2250	0.5989	0.071*
H22S	−0.0038	0.2567	0.6338	0.071*
H23S	0.0077	0.1786	0.6400	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.02420 (6)	0.01553 (5)	0.02259 (6)	−0.00050 (5)	−0.00066 (8)	0.00298 (8)
Cu	0.01321 (10)	0.01381 (10)	0.01374 (10)	0.00034 (8)	−0.00041 (14)	0.00155 (13)
P1	0.0120 (2)	0.0155 (2)	0.0155 (2)	−0.0003 (2)	−0.0003 (2)	0.0000 (2)
P2	0.0126 (2)	0.0172 (3)	0.0174 (3)	−0.0001 (2)	−0.0028 (2)	0.0018 (2)
P3	0.0143 (2)	0.0160 (2)	0.0132 (2)	0.0010 (2)	0.0002 (2)	0.0014 (2)
C1	0.0116 (10)	0.0240 (11)	0.0179 (11)	−0.0007 (8)	0.0006 (8)	−0.0002 (9)
C2	0.0157 (10)	0.0236 (12)	0.0230 (12)	−0.0015 (9)	0.0021 (9)	−0.0027 (9)
C3	0.0206 (12)	0.0366 (15)	0.0249 (13)	−0.0027 (10)	0.0038 (10)	−0.0104 (11)
C4	0.0241 (13)	0.0509 (18)	0.0154 (12)	−0.0049 (12)	0.0013 (10)	−0.0033 (11)
C5	0.0244 (13)	0.0401 (15)	0.0206 (12)	0.0013 (11)	−0.0017 (10)	0.0055 (11)
C6	0.0206 (12)	0.0228 (12)	0.0218 (12)	−0.0005 (10)	−0.0002 (10)	0.0006 (10)
C7	0.0169 (9)	0.0173 (9)	0.0185 (14)	0.0015 (7)	0.0008 (8)	0.0002 (8)
C8	0.0177 (10)	0.0211 (11)	0.0185 (10)	0.0006 (9)	−0.0022 (8)	−0.0024 (9)
C9	0.0200 (12)	0.0283 (13)	0.0203 (11)	0.0055 (9)	−0.0036 (9)	0.0039 (10)
C10	0.0249 (12)	0.0218 (12)	0.0280 (13)	0.0035 (10)	0.0030 (10)	0.0092 (10)
C11	0.0222 (9)	0.0189 (9)	0.0291 (11)	−0.0037 (7)	0.0009 (13)	0.0022 (13)
C12	0.0157 (10)	0.0226 (11)	0.0232 (11)	−0.0019 (9)	−0.0031 (8)	0.0029 (9)
C13	0.0150 (10)	0.0178 (10)	0.0230 (12)	−0.0018 (8)	−0.0027 (9)	0.0026 (9)
C14	0.0248 (11)	0.0211 (10)	0.0346 (18)	−0.0005 (9)	−0.0096 (11)	−0.0008 (10)
C15	0.0322 (14)	0.0226 (12)	0.0459 (19)	−0.0054 (10)	−0.0181 (12)	0.0014 (11)
C16	0.0229 (14)	0.0332 (14)	0.0518 (18)	−0.0130 (11)	−0.0144 (12)	0.0186 (13)
C17	0.0171 (12)	0.0432 (17)	0.0407 (16)	−0.0053 (11)	0.0000 (11)	0.0120 (13)
C18	0.0177 (11)	0.0324 (13)	0.0267 (13)	−0.0043 (10)	−0.0006 (10)	0.0006 (10)
C19	0.0142 (10)	0.0236 (11)	0.0209 (12)	0.0029 (8)	−0.0005 (8)	0.0045 (9)
C20	0.0173 (11)	0.0271 (13)	0.0456 (17)	0.0003 (10)	−0.0036 (11)	−0.0096 (12)
C21	0.0156 (11)	0.0315 (14)	0.061 (2)	−0.0016 (10)	−0.0024 (12)	−0.0061 (13)
C22	0.0188 (11)	0.0398 (14)	0.0358 (19)	0.0023 (10)	0.0044 (10)	−0.0006 (12)
C23	0.0265 (13)	0.0368 (15)	0.0247 (13)	0.0042 (11)	0.0009 (10)	−0.0074 (11)
C24	0.0200 (10)	0.0278 (11)	0.0211 (13)	−0.0018 (8)	−0.0040 (10)	−0.0030 (11)
C25	0.0142 (10)	0.0173 (10)	0.0215 (11)	−0.0003 (8)	−0.0056 (8)	0.0005 (9)
C26	0.0177 (11)	0.0200 (11)	0.0240 (12)	−0.0007 (8)	−0.0041 (9)	−0.0008 (9)
C27	0.0230 (13)	0.0271 (14)	0.0297 (14)	0.0015 (10)	−0.0045 (10)	−0.0076 (11)
C28	0.0274 (13)	0.0167 (12)	0.0500 (18)	0.0026 (10)	−0.0110 (12)	−0.0033 (11)
C29	0.0251 (13)	0.0199 (12)	0.0442 (16)	−0.0019 (10)	−0.0048 (11)	0.0080 (11)
C30	0.0181 (11)	0.0213 (11)	0.0283 (13)	−0.0004 (9)	−0.0017 (9)	0.0027 (10)
C31	0.0204 (12)	0.0199 (12)	0.0173 (11)	0.0055 (9)	−0.0024 (9)	0.0031 (9)
C32	0.0242 (13)	0.0236 (12)	0.0218 (12)	0.0003 (10)	−0.0057 (10)	0.0040 (10)
C33	0.0407 (16)	0.0260 (13)	0.0291 (14)	−0.0029 (12)	−0.0073 (12)	0.0101 (11)
C34	0.0523 (19)	0.0359 (16)	0.0248 (14)	0.0049 (14)	−0.0123 (13)	0.0097 (12)
C35	0.055 (2)	0.0293 (15)	0.0269 (14)	0.0028 (13)	−0.0216 (14)	−0.0001 (11)
C36	0.0380 (15)	0.0233 (13)	0.0292 (14)	−0.0009 (11)	−0.0147 (13)	0.0009 (11)
C37	0.0191 (12)	0.0250 (12)	0.0139 (11)	−0.0024 (9)	−0.0014 (9)	0.0040 (9)
C38	0.0346 (14)	0.0217 (12)	0.0221 (12)	−0.0049 (10)	−0.0064 (11)	0.0021 (10)
C39	0.0541 (19)	0.0272 (14)	0.0288 (15)	−0.0167 (13)	−0.0190 (13)	0.0082 (11)
C40	0.0323 (15)	0.0476 (18)	0.0408 (17)	−0.0187 (13)	−0.0207 (13)	0.0226 (15)
C41	0.0196 (13)	0.062 (2)	0.0425 (18)	0.0019 (13)	−0.0091 (12)	0.0101 (16)
C42	0.0207 (12)	0.0451 (17)	0.0250 (13)	0.0064 (12)	−0.0041 (10)	−0.0021 (12)
C43	0.0148 (10)	0.0194 (11)	0.0206 (11)	0.0020 (8)	0.0017 (8)	0.0049 (9)
C44	0.0335 (14)	0.0195 (11)	0.0257 (13)	−0.0020 (10)	0.0028 (11)	0.0022 (9)
C45	0.0489 (18)	0.0183 (12)	0.0467 (19)	−0.0020 (12)	0.0093 (15)	0.0025 (12)
C46	0.0321 (15)	0.0252 (15)	0.053 (2)	0.0040 (12)	0.0123 (14)	0.0181 (14)
C47	0.0240 (13)	0.0397 (16)	0.0324 (15)	0.0034 (11)	0.0027 (11)	0.0208 (12)
C48	0.0224 (12)	0.0327 (14)	0.0209 (12)	0.0016 (10)	−0.0015 (9)	0.0092 (10)
C49	0.0180 (11)	0.0224 (12)	0.0141 (11)	0.0052 (9)	0.0027 (9)	0.0012 (9)
C50	0.0251 (12)	0.0241 (13)	0.0193 (12)	0.0030 (10)	0.0008 (9)	0.0009 (10)
C51	0.0329 (14)	0.0241 (12)	0.0209 (12)	0.0097 (11)	0.0000 (10)	0.0006 (10)
C52	0.0266 (13)	0.0379 (15)	0.0252 (13)	0.0155 (11)	0.0063 (10)	0.0027 (11)
C53	0.0222 (12)	0.0368 (15)	0.0308 (14)	0.0056 (11)	0.0082 (10)	0.0077 (12)
C54	0.0184 (11)	0.0246 (12)	0.0224 (12)	0.0034 (9)	0.0043 (10)	0.0053 (10)
N1S	0.106 (3)	0.055 (2)	0.053 (2)	0.026 (2)	−0.039 (2)	−0.0197 (17)
C1S	0.0500 (19)	0.0309 (15)	0.0418 (18)	0.0090 (13)	−0.0135 (15)	−0.0073 (13)
C2S	0.054 (2)	0.052 (2)	0.0363 (18)	−0.0011 (16)	−0.0160 (15)	0.0016 (15)

Geometric parameters (Å, º) top

Cu—I	2.6843 (3)	C26—C27	1.398 (4)
Cu—P1	2.3421 (6)	C26—H26	0.9500
Cu—P2	2.3463 (6)	C27—C28	1.385 (4)
Cu—P3	2.3295 (7)	C27—H27	0.9500
P1—C7	1.830 (2)	C28—C29	1.384 (4)
P1—C1	1.833 (2)	C28—H28	0.9500
P1—C13	1.838 (2)	C29—C30	1.395 (4)
P2—C19	1.833 (2)	C29—H29	0.9500
P2—C31	1.839 (3)	C30—H30	0.9500
P2—C25	1.840 (2)	C31—C32	1.389 (4)
P3—C43	1.827 (2)	C31—C36	1.392 (4)
P3—C37	1.831 (3)	C32—C33	1.389 (4)
P3—C49	1.834 (3)	C32—H32	0.9500
C1—C6	1.394 (3)	C33—C34	1.385 (4)
C1—C2	1.397 (3)	C33—H33	0.9500
C2—C3	1.395 (4)	C34—C35	1.383 (4)
C2—H2	0.9500	C34—H34	0.9500
C3—C4	1.388 (4)	C35—C36	1.395 (4)
C3—H3	0.9500	C35—H35	0.9500
C4—C5	1.378 (4)	C36—H36	0.9500
C4—H4	0.9500	C37—C42	1.389 (4)
C5—C6	1.389 (4)	C37—C38	1.392 (4)
C5—H5	0.9500	C38—C39	1.406 (4)
C6—H6	0.9500	C38—H38	0.9500
C7—C8	1.390 (3)	C39—C40	1.374 (5)
C7—C12	1.408 (3)	C39—H39	0.9500
C8—C9	1.399 (3)	C40—C41	1.385 (5)
C8—H8	0.9500	C40—H40	0.9500
C9—C10	1.380 (4)	C41—C42	1.392 (4)
C9—H9	0.9500	C41—H41	0.9500
C10—C11	1.385 (4)	C42—H42	0.9500
C10—H10	0.9500	C43—C44	1.376 (4)
C11—C12	1.391 (3)	C43—C48	1.402 (3)
C11—H11	0.9500	C44—C45	1.401 (4)
C12—H12	0.9500	C44—H44	0.9500
C13—C14	1.384 (3)	C45—C46	1.367 (5)
C13—C18	1.403 (4)	C45—H45	0.9500
C14—C15	1.401 (3)	C46—C47	1.374 (5)
C14—H14	0.9500	C46—H46	0.9500
C15—C16	1.377 (4)	C47—C48	1.394 (4)
C15—H15	0.9500	C47—H47	0.9500
C16—C17	1.383 (5)	C48—H48	0.9500
C16—H16	0.9500	C49—C54	1.393 (4)
C17—C18	1.386 (4)	C49—C50	1.401 (4)
C17—H17	0.9500	C50—C51	1.395 (4)
C18—H18	0.9500	C50—H50	0.9500
C19—C24	1.388 (4)	C51—C52	1.382 (4)
C19—C20	1.397 (3)	C51—H51	0.9500
C20—C21	1.396 (4)	C52—C53	1.380 (4)
C20—H20	0.9500	C52—H52	0.9500
C21—C22	1.378 (4)	C53—C54	1.393 (4)
C21—H21	0.9500	C53—H53	0.9500
C22—C23	1.378 (4)	C54—H54	0.9500
C22—H22	0.9500	N1S—C1S	1.130 (5)
C23—C24	1.400 (3)	C1S—C2S	1.447 (5)
C23—H23	0.9500	C2S—H21S	0.9800
C24—H24	0.9500	C2S—H22S	0.9800
C25—C30	1.396 (3)	C2S—H23S	0.9800
C25—C26	1.402 (3)

P1—Cu—P2	108.39 (2)	C30—C25—P2	120.9 (2)
P3—Cu—P1	115.80 (2)	C26—C25—P2	120.1 (2)
P3—Cu—P2	115.77 (2)	C27—C26—C25	120.3 (2)
P1—Cu—I	104.75 (2)	C27—C26—H26	119.9
P2—Cu—I	113.66 (2)	C25—C26—H26	119.9
P3—Cu—I	97.69 (2)	C28—C27—C26	120.1 (3)
C7—P1—C1	104.4 (1)	C28—C27—H27	119.9
C7—P1—C13	102.2 (1)	C26—C27—H27	119.9
C1—P1—C13	100.2 (1)	C29—C28—C27	120.1 (3)
C7—P1—Cu	115.01 (7)	C29—C28—H28	119.9
C1—P1—Cu	111.79 (8)	C27—C28—H28	119.9
C13—P1—Cu	121.07 (8)	C28—C29—C30	120.1 (3)
C19—P2—C31	100.1 (1)	C28—C29—H29	120.0
C19—P2—C25	103.6 (1)	C30—C29—H29	120.0
C31—P2—C25	102.3 (1)	C29—C30—C25	120.7 (2)
C19—P2—Cu	116.27 (8)	C29—C30—H30	119.7
C31—P2—Cu	118.89 (9)	C25—C30—H30	119.7
C25—P2—Cu	113.51 (7)	C32—C31—C36	119.2 (2)
C43—P3—C37	99.4 (1)	C32—C31—P2	118.7 (2)
C43—P3—C49	103.4 (1)	C36—C31—P2	122.1 (2)
C37—P3—C49	104.9 (1)	C33—C32—C31	120.5 (3)
C43—P3—Cu	117.71 (8)	C33—C32—H32	119.7
C37—P3—Cu	112.29 (8)	C31—C32—H32	119.7
C49—P3—Cu	117.04 (8)	C34—C33—C32	120.0 (3)
C6—C1—C2	118.6 (2)	C34—C33—H33	120.0
C6—C1—P1	116.1 (2)	C32—C33—H33	120.0
C2—C1—P1	125.2 (2)	C35—C34—C33	120.0 (3)
C3—C2—C1	120.4 (2)	C35—C34—H34	120.0
C3—C2—H2	119.8	C33—C34—H34	120.0
C1—C2—H2	119.8	C34—C35—C36	120.1 (3)
C4—C3—C2	120.0 (2)	C34—C35—H35	120.0
C4—C3—H3	120.0	C36—C35—H35	120.0
C2—C3—H3	120.0	C31—C36—C35	120.1 (3)
C5—C4—C3	120.0 (2)	C31—C36—H36	119.9
C5—C4—H4	120.0	C35—C36—H36	119.9
C3—C4—H4	120.0	C42—C37—C38	119.0 (2)
C4—C5—C6	120.2 (3)	C42—C37—P3	115.2 (2)
C4—C5—H5	119.9	C38—C37—P3	125.8 (2)
C6—C5—H5	119.9	C37—C38—C39	119.5 (3)
C5—C6—C1	120.8 (2)	C37—C38—H38	120.2
C5—C6—H6	119.6	C39—C38—H38	120.2
C1—C6—H6	119.6	C40—C39—C38	120.5 (3)
C8—C7—C12	118.7 (2)	C40—C39—H39	119.7
C8—C7—P1	122.0 (2)	C38—C39—H39	119.7
C12—C7—P1	119.2 (2)	C39—C40—C41	120.3 (3)
C7—C8—C9	120.4 (2)	C39—C40—H40	119.8
C7—C8—H8	119.8	C41—C40—H40	119.8
C9—C8—H8	119.8	C40—C41—C42	119.3 (3)
C10—C9—C8	120.3 (2)	C40—C41—H41	120.4
C10—C9—H9	119.8	C42—C41—H41	120.4
C8—C9—H9	119.8	C37—C42—C41	121.3 (3)
C9—C10—C11	119.9 (2)	C37—C42—H42	119.4
C9—C10—H10	120.0	C41—C42—H42	119.4
C11—C10—H10	120.0	C44—C43—C48	118.9 (2)
C10—C11—C12	120.3 (2)	C44—C43—P3	118.6 (2)
C10—C11—H11	119.9	C48—C43—P3	122.5 (2)
C12—C11—H11	119.9	C43—C44—C45	121.0 (3)
C11—C12—C7	120.4 (2)	C43—C44—H44	119.5
C11—C12—H12	119.8	C45—C44—H44	119.5
C7—C12—H12	119.8	C46—C45—C44	119.4 (3)
C14—C13—C18	118.8 (2)	C46—C45—H45	120.3
C14—C13—P1	120.6 (2)	C44—C45—H45	120.3
C18—C13—P1	120.6 (2)	C45—C46—C47	120.7 (3)
C13—C14—C15	119.9 (3)	C45—C46—H46	119.6
C13—C14—H14	120.1	C47—C46—H46	119.6
C15—C14—H14	120.1	C46—C47—C48	120.2 (3)
C16—C15—C14	120.7 (3)	C46—C47—H47	119.9
C16—C15—H15	119.6	C48—C47—H47	119.9
C14—C15—H15	119.6	C47—C48—C43	119.7 (3)
C15—C16—C17	119.8 (2)	C47—C48—H48	120.1
C15—C16—H16	120.1	C43—C48—H48	120.1
C17—C16—H16	120.1	C54—C49—C50	118.4 (2)
C16—C17—C18	119.9 (3)	C54—C49—P3	121.5 (2)
C16—C17—H17	120.1	C50—C49—P3	120.0 (2)
C18—C17—H17	120.1	C51—C50—C49	120.6 (2)
C17—C18—C13	120.9 (3)	C51—C50—H50	119.7
C17—C18—H18	119.6	C49—C50—H50	119.7
C13—C18—H18	119.6	C52—C51—C50	120.1 (2)
C24—C19—C20	119.1 (2)	C52—C51—H51	119.9
C24—C19—P2	118.0 (2)	C50—C51—H51	119.9
C20—C19—P2	122.7 (2)	C53—C52—C51	119.8 (2)
C21—C20—C19	120.1 (3)	C53—C52—H52	120.1
C21—C20—H20	120.0	C51—C52—H52	120.1
C19—C20—H20	120.0	C52—C53—C54	120.5 (2)
C22—C21—C20	120.4 (3)	C52—C53—H53	119.8
C22—C21—H21	119.8	C54—C53—H53	119.8
C20—C21—H21	119.8	C49—C54—C53	120.6 (2)
C23—C22—C21	119.9 (2)	C49—C54—H54	119.7
C23—C22—H22	120.0	C53—C54—H54	119.7
C21—C22—H22	120.0	N1S—C1S—C2S	179.3 (4)
C22—C23—C24	120.3 (2)	C1S—C2S—H21S	109.5
C22—C23—H23	119.8	C1S—C2S—H22S	109.5
C24—C23—H23	119.8	H21S—C2S—H22S	109.5
C19—C24—C23	120.2 (2)	C1S—C2S—H23S	109.5
C19—C24—H24	119.9	H21S—C2S—H23S	109.5
C23—C24—H24	119.9	H22S—C2S—H23S	109.5
C30—C25—C26	118.7 (2)

P3—Cu—P1—C7	−41.42 (8)	C19—C20—C21—C22	−1.9 (5)
P2—Cu—P1—C7	90.62 (8)	C20—C21—C22—C23	0.4 (5)
I—Cu—P1—C7	−147.73 (8)	C21—C22—C23—C24	0.9 (4)
P3—Cu—P1—C1	−160.21 (9)	C20—C19—C24—C23	−0.9 (4)
P2—Cu—P1—C1	−28.18 (9)	P2—C19—C24—C23	−176.1 (2)
I—Cu—P1—C1	93.47 (9)	C22—C23—C24—C19	−0.6 (4)
P3—Cu—P1—C13	82.11 (9)	C19—P2—C25—C30	43.1 (2)
P2—Cu—P1—C13	−145.85 (9)	C31—P2—C25—C30	146.78 (19)
I—Cu—P1—C13	−24.20 (9)	Cu—P2—C25—C30	−83.89 (19)
P3—Cu—P2—C19	−32.45 (9)	C19—P2—C25—C26	−142.59 (19)
P1—Cu—P2—C19	−164.50 (9)	C31—P2—C25—C26	−38.9 (2)
I—Cu—P2—C19	79.49 (9)	Cu—P2—C25—C26	90.42 (19)
P3—Cu—P2—C31	−152.11 (10)	C30—C25—C26—C27	−0.8 (3)
P1—Cu—P2—C31	75.84 (10)	P2—C25—C26—C27	−175.18 (18)
I—Cu—P2—C31	−40.17 (10)	C25—C26—C27—C28	−0.1 (4)
P3—Cu—P2—C25	87.57 (9)	C26—C27—C28—C29	1.1 (4)
P1—Cu—P2—C25	−44.48 (9)	C27—C28—C29—C30	−1.3 (4)
I—Cu—P2—C25	−160.49 (8)	C28—C29—C30—C25	0.5 (4)
P1—Cu—P3—C43	63.46 (9)	C26—C25—C30—C29	0.6 (3)
P2—Cu—P3—C43	−65.03 (9)	P2—C25—C30—C29	174.95 (19)
I—Cu—P3—C43	173.98 (8)	C19—P2—C31—C32	−105.8 (2)
P1—Cu—P3—C37	−51.02 (10)	C25—P2—C31—C32	147.8 (2)
P2—Cu—P3—C37	−179.52 (9)	Cu—P2—C31—C32	21.9 (2)
I—Cu—P3—C37	59.50 (9)	C19—P2—C31—C36	72.3 (3)
P1—Cu—P3—C49	−172.41 (10)	C25—P2—C31—C36	−34.1 (3)
P2—Cu—P3—C49	59.10 (10)	Cu—P2—C31—C36	−160.0 (2)
I—Cu—P3—C49	−61.89 (10)	C36—C31—C32—C33	2.6 (4)
C7—P1—C1—C6	−177.91 (18)	P2—C31—C32—C33	−179.3 (2)
C13—P1—C1—C6	76.6 (2)	C31—C32—C33—C34	−0.5 (5)
Cu—P1—C1—C6	−53.0 (2)	C32—C33—C34—C35	−1.6 (5)
C7—P1—C1—C2	3.1 (2)	C33—C34—C35—C36	1.6 (5)
C13—P1—C1—C2	−102.4 (2)	C32—C31—C36—C35	−2.7 (4)
Cu—P1—C1—C2	128.07 (19)	P2—C31—C36—C35	179.3 (2)
C6—C1—C2—C3	0.0 (3)	C34—C35—C36—C31	0.6 (5)
P1—C1—C2—C3	178.94 (19)	C43—P3—C37—C42	−63.8 (2)
C1—C2—C3—C4	−0.1 (4)	C49—P3—C37—C42	−170.4 (2)
C2—C3—C4—C5	0.3 (4)	Cu—P3—C37—C42	61.5 (2)
C3—C4—C5—C6	−0.3 (4)	C43—P3—C37—C38	115.7 (2)
C4—C5—C6—C1	0.2 (4)	C49—P3—C37—C38	9.1 (3)
C2—C1—C6—C5	0.0 (4)	Cu—P3—C37—C38	−119.0 (2)
P1—C1—C6—C5	−179.1 (2)	C42—C37—C38—C39	−1.6 (4)
C1—P1—C7—C8	−122.92 (19)	P3—C37—C38—C39	178.9 (2)
C13—P1—C7—C8	−18.9 (2)	C37—C38—C39—C40	−0.2 (4)
Cu—P1—C7—C8	114.23 (18)	C38—C39—C40—C41	1.6 (4)
C1—P1—C7—C12	61.5 (2)	C39—C40—C41—C42	−1.1 (5)
C13—P1—C7—C12	165.52 (19)	C38—C37—C42—C41	2.2 (4)
Cu—P1—C7—C12	−61.40 (19)	P3—C37—C42—C41	−178.3 (2)
C12—C7—C8—C9	0.9 (3)	C40—C41—C42—C37	−0.8 (5)
P1—C7—C8—C9	−174.72 (18)	C37—P3—C43—C44	135.0 (2)
C7—C8—C9—C10	−1.3 (4)	C49—P3—C43—C44	−117.1 (2)
C8—C9—C10—C11	0.2 (4)	Cu—P3—C43—C44	13.6 (2)
C9—C10—C11—C12	1.2 (4)	C37—P3—C43—C48	−42.6 (2)
C10—C11—C12—C7	−1.5 (4)	C49—P3—C43—C48	65.2 (2)
C8—C7—C12—C11	0.4 (4)	Cu—P3—C43—C48	−164.05 (17)
P1—C7—C12—C11	176.2 (2)	C48—C43—C44—C45	−0.9 (4)
C7—P1—C13—C14	104.3 (2)	P3—C43—C44—C45	−178.6 (2)
C1—P1—C13—C14	−148.4 (2)	C43—C44—C45—C46	1.1 (4)
Cu—P1—C13—C14	−25.1 (2)	C44—C45—C46—C47	−0.1 (5)
C7—P1—C13—C18	−73.6 (2)	C45—C46—C47—C48	−1.2 (4)
C1—P1—C13—C18	33.7 (2)	C46—C47—C48—C43	1.4 (4)
Cu—P1—C13—C18	157.04 (17)	C44—C43—C48—C47	−0.3 (4)
C18—C13—C14—C15	0.9 (4)	P3—C43—C48—C47	177.28 (19)
P1—C13—C14—C15	−177.04 (19)	C43—P3—C49—C54	18.8 (2)
C13—C14—C15—C16	−1.4 (4)	C37—P3—C49—C54	122.4 (2)
C14—C15—C16—C17	0.5 (4)	Cu—P3—C49—C54	−112.4 (2)
C15—C16—C17—C18	0.8 (4)	C43—P3—C49—C50	−166.1 (2)
C16—C17—C18—C13	−1.3 (4)	C37—P3—C49—C50	−62.4 (2)
C14—C13—C18—C17	0.5 (4)	Cu—P3—C49—C50	62.8 (2)
P1—C13—C18—C17	178.4 (2)	C54—C49—C50—C51	−1.8 (4)
C31—P2—C19—C24	98.0 (2)	P3—C49—C50—C51	−177.1 (2)
C25—P2—C19—C24	−156.6 (2)	C49—C50—C51—C52	0.9 (4)
Cu—P2—C19—C24	−31.4 (2)	C50—C51—C52—C53	0.7 (4)
C31—P2—C19—C20	−77.0 (2)	C51—C52—C53—C54	−1.4 (4)
C25—P2—C19—C20	28.4 (2)	C50—C49—C54—C53	1.2 (4)
Cu—P2—C19—C20	153.61 (19)	P3—C49—C54—C53	176.4 (2)
C24—C19—C20—C21	2.1 (4)	C52—C53—C54—C49	0.4 (4)
P2—C19—C20—C21	177.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1ⁱ	0.95	2.94	3.732	141
C40—H40···Cg2ⁱ	0.95	2.94	3.696	137
C39—H39···N1Sⁱⁱ	0.95	2.58	3.468 (4)	157

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

Experimental details

Crystal data
Chemical formula	[CuI(C₁₈H₁₅P)₃]·C₂H₃N
M_r	1018.30
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	115
a, b, c (Å)	18.573 (1), 20.263 (1), 12.7839 (5)
V (Å³)	4811.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.30 × 0.25 × 0.17

Data collection
Diffractometer	Nonius KappaCCD diffractometer (with an Oxford Cryosystems Cryostream cooler)
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.709, 0.818
No. of measured, independent and observed [I > 2σ(I)] reflections	156685, 15969, 13488
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.742

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.068, 1.03
No. of reflections	15969
No. of parameters	561
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.66
Absolute structure	Flack (1983)
Absolute structure parameter	0.478 (8)

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1ⁱ	0.95	2.94	3.732	141
C40—H40···Cg2ⁱ	0.95	2.94	3.696	137
C39—H39···N1Sⁱⁱ	0.95	2.58	3.468 (4)	156.8

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

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

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