Crystal structure of fac-tricarbon­yl(quinoline-2-carboxyl­ato-κ2N,O)(tri­phenyl­arsane-κAs)rhenium(I)

Triantis, C.; Shegani, A.; Kiritsis, C.; Raptopoulou, C.P.; Psycharis, V.; Pelecanou, M.; Pirmettis, I.; Papadopoulos, M.

doi:10.1107/S2056989015024640

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ISSN: 2056-9890

Volume 72| Part 2| February 2016| Pages 114-116

doi:10.1107/S2056989015024640

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Crystal structure of fac-tricarbonyl(quinoline-2-carboxylato-κ²N,O)(triphenylarsane-κAs)rhenium(I)

Charalampos Triantis,^a Antonio Shegani,^a Christos Kiritsis,^a Catherine P. Raptopoulou,^b Vassilis Psycharis,^b ^* Maria Pelecanou,^c Ioannis Pirmettis ^a and Minas Papadopoulos ^a

^aInstitute of Nuclear and Radiological Sciences and Technology, Energy and Safety, National Centre for Scientific Research "Demokritos", 15310 Athens, Greece, ^bInstitute of Nanoscience and Nanotechnology, National Centre for Scientific Research "Demokritos", 15310 Athens, Greece, and ^cInstitute of Biosciences & Applications, National Centre for Scientific Research "Demokritos", 15310 Athens, Greece
^*Correspondence e-mail: v.psycharis@inn.demokritos.gr

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 November 2015; accepted 22 December 2015; online 6 January 2016)

In the title compound, [Re(C₁₀H₆NO₂)(CO)₃{As(C₆H₅)₃}], the coordination environment of Re^I is that of a distorted octahedron. Three coordination sites are occupied by three carbonyl groups in a facial arrangement and the remaining three sites by triphenylarsane and deprotonated quinaldic acid in As-mono- and N,O-bidentate fashions, respectively. In the crystal, the complexes are linked through weak C—H⋯O hydrogen bonds, forming a three-dimensional network. It worth noting that, as far as we know, this complex is the first Re^I triphenylarsane tricarbonyl compound to be reported.

Keywords: crystal structure; rhenium(I) tricarbonyl complex; rhenium(I) triphenylarsane and quinaldic acid complex; trans influence.

CCDC reference: 1443806

1. Chemical context

In recent years, Re and Tc radiopharmaceutical chemistry with the tricarbonyl precursor fac-[M(CO)₃(H₂O)₃]⁺ (M = ^99mTc, Re) has expanded continuously with the development of suitably derivatized novel ligand systems which efficiently displace the coordinating water molecules to produce complexes with high in vivo stability, favorable pharmacokinetic properties, and target tissue specificity (Mundwiler et al., 2004 ; Triantis et al., 2013 ; Jürgens et al., 2014 ; Alberto, 2012 ). In this article, we describe the crystal structure of a `2 + 1' tricarbonyl rhenium(I) complex, fac-[M(CO)₃(L)(NO-QA)], where L is triphenylarsane and NO-QA deprotonated quinaldic acid. This study is part of our ongoing research in the field of rhenium coordination compounds, particularly complexes bearing the fac-[Re(CO)₃]⁺ synthon, to develop new molecular radiopharmaceuticals. Related rhenium(I) tricarbonyl complexes have been reported by Schutte et al. (2011 ) and Manicum et al. (2015 ).

2. Structural commentary

In the title compound, the Re^I cation is in a distorted octahedral environment (Fig. 1). The apical positions of the octahedron are occupied by the monodentate arsane ligand and one of the carbonyl groups (C34≡O32). The rhenium atom lies almost on the equatorial plane [displacement = 0.0459 (6) Å]. The five-membered ring defined by the metal ion and the chelating bidentate NO-QA anion is almost planar [maximum deviation of 0.078 (6) Å for atom N1]. One phenyl ring (C11–C16) of the triphenylarsane ligand exhibits intramolecular π–π interaction with the NO-QA ligand (Fig. 1), the distance from the centroid of the phenyl ring to the plane of the NO-QA ligand being 3.495 Å and the angle between the planes being 9.1°. In addition, intramolecular hydrogen bonds are established between the phenyl rings of the NO-QA ligand (C9—H9⋯O31) and between one of the phenyl rings of the triphenylarsane ligand (C24—H24⋯O1) with one carbonyl oxygen atom and one carboxylate oxygen atom respectively (Fig.1; Table 1). The Re—C≡O bond length in the apical position [Re—C34: 1.937 (12) Å] is longer than those in the equatorial plane [Re—C32 = 1.893 (8) Å and Re—C30 = 1.904 (9) Å] because of the trans influence of the triphenylarsane ligands, as expected (Coe & Glenwright, 2000 ; Otto & Johansson, 2002 ). Taking into account that this is the first structurally characterized Re^I triphenylarsane tricarbonyl complex, there are no other Re^I compound to compare with, but the measured Re—As distance of 2.5855 (10) Å is close to those given by Commons & Hoskins (1975 ) of 2.569–2.584 Å where the di(diphenylarsino)methane ligand is coordinating to an Re^I ion.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O31	0.95	2.60	3.431 (11)	146
C24—H24⋯O1	0.95	2.47	3.276 (12)	143
C7—H7⋯O2ⁱ	0.95	2.20	3.151 (11)	176
C21—H21⋯O2ⁱⁱ	0.95	2.57	3.251 (11)	128
C19—H19⋯O2ⁱⁱⁱ	0.95	2.46	3.337 (11)	153
Symmetry codes: (i) x, y+1, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure and atom-labelling scheme of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity, except for those involved in intramolecular hydrogen bonding (dashed grey lines).

3. Supramolecular features

Weak intermolecular hydrogen bonds (C7—H7⋯O2, C19—H19⋯O2 and C21—H21⋯O2, Table 1 and Fig. 2) are developed among the complexes in the crystal structure. Those of the C7—H7⋯O2 type result in chain formation parallel to the b axis (Fig. 3). Neighbouring chains further interact through C19—H19⋯O2 and C21—H21⋯O2 interactions and build up the three-dimensional set-up of the structure (Fig. 4).

Figure 2
Weak intermolecular hydrogen bonds (C7—H7⋯O2, C19—H19⋯O2 and C21—H21⋯O2) between neighbouring complexes indicated by dashed orange, yellow and turquoise lines, respectively. Intramolecular hydrogen bonds are not shown for clarity.

Figure 3
Chains of complexes, formed through C7—H7⋯O2 hydrogen bonds (dashed orange lines), parallel to the b axis.

Figure 4
The three-dimensional network of neighbouring chains formed through C19—H19⋯O2 and C21—H21⋯O2 hydrogen bonds (dashed orange and dashed turquoise lines, respectively) in a view along the b-axis direction.

4. Synthesis and crystallization

To a stirred solution of quinaldic acid (17.3 mg, 0.1 mmol) in 5 ml methanol, a solution of [NEt₄]₂[ReBr₃(CO)₃] (77 mg, 0.1 mmol) in 5 ml methanol was added. The mixture was heated at 323 K and after 30 min a solution of triphenylarsane (0.1 mmol) in 3 ml methanol was added. The mixture was stirred under reflux for 2 h and the reaction progress was monitored by HPLC. The solvent was removed under reduced pressure and the solid residue was recrystallized from a dichloromethane/methanol mixture. The resulting solid was redissolved in a minimum volume of dichloromethane, layered with methanol and left to stand at room temperature. After several days crystals suitable for X-ray analysis were isolated (yield: 46.8 mg, 60%).

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound H atoms were placed in idealized positions and refined using a riding model with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	[Re(C₁₀H₆NO₂)(C₁₈H₁₅As)(CO)₃]
M_r	748.61
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	160
a, b, c (Å)	18.1637 (3), 10.3463 (2), 14.5322 (3)
V (Å³)	2730.99 (9)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	10.40
Crystal size (mm)	0.27 × 0.27 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS SPIDER IPDS diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005 )
T_min, T_max	0.443, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	16386, 4768, 4655
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.05
No. of reflections	4768
No. of parameters	352
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.39, −1.50
Absolute structure	Flack x determined using 2096 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.019 (7)
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), DIAMOND (Crystal Impact, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1443806

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015024640/wm5246sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015024640/wm5246Isup2.hkl

checkCIF report

Chemical context top

In recent years, Re and Tc radiopharmaceutical chemistry with the tricarbonyl precursor fac-[M(CO)₃(H₂O)₃]⁺ (M = ^99mTc, Re) has expanded continuously with the development of suitably derivatized novel ligand systems which efficiently displace the coordinating water molecules to produce complexes with high in vivo stability, favorable pharmacokinetic properties, and target tissue specificity (Mundwiler et al., 2004; Triantis et al., 2013; Jürgens et al., 2014; Alberto, 2012). In this article, we describe the crystal structure of a `2+1' tricarbonyl rhenium(I) complex, fac-[M(CO)₃(L)(NO—QA)], where L is triphenylarsane and NO—QA deprotonated quinaldic acid. This study is part of our ongoing research in the field of rhenium coordination compounds, particularly complexes bearing the fac-[Re(CO)₃]⁺ synthon, to develop new molecular radiopharmaceuticals. Related rhenium(I) tricarbonyl complexes have been reported by Schutte et al. (2011) and Manicum et al. (2015).

Structural commentary top

In the title compound, the Re^I cation is in a distorted octahedral environment (Fig. 1). The apical positions of the octahedron are occupied by the monodentate arsane ligand and one of the carbonyl groups (C34≡O32). The rhenium atom lies almost on the equatorial plane [displacement = 0.0459 (6) Å]. The five-membered ring defined by the metal ion and the chelating bidentate NO—QA anion is almost planar [maximum deviation of 0.078 (6) Å for atom N1]. One phenyl ring (C11–C16) of the triphenylarsane ligand exhibits intramolecular π–π interaction with the NO—QA ligand (Fig. 1), the distance from the centroid of the phenyl ring to the plane of the NO—QA ligand being 3.495 Å and the angle between the planes being 9.1°. In addition, intramolecular hydrogen bonds are established between the phenyl rings of the NO—QA ligand (C9—H9···O31) and between one of the phenyl rings of the triphenylarsane ligand (C24—H24···O1) with one carbonyl oxygen atom and one carboxylate oxygen atom respectively (Fig.1; Table 1). The Re—C≡O bond length in the apical position [Re—C34: 1.937 (12) Å] is longer than those in the equatorial plane [Re—C32 = 1.893 (8) Å and Re—C30 = 1.904 (9) Å] because of the trans influence of the triphenylarsane ligands, as expected (Coe & Glenwright, 2000; Otto & Johansson, 2002). Taking into account that this is the first structurally characterized Re^I triphenylarsane tricarbonyl complex, there are no other Re^I compound to compare with, but the measured Re—As distance of 2.5855 (10) Å is close to those given by Commons & Hoskins (1975) of 2.569–2.584 Å where the di(diphenylarsino)methane ligand is coordinating to an Re^I ion.

Supramolecular features top

Weak intermolecular hydrogen bonds (C7—H7···O2, C19—H19···O2 and C21—H21···O2, Table 1 and Fig. 2) are developed among the complexes in the crystal structure. Those of the C7—H7···O2 type result in chain formation parallel to the b-axis direction (Fig. 3). Neighbouring chains further interact through C19—H19···O2 and C21—H21···O2 interactions and build up the three-dimensional set-up of the structure (Fig. 4).

Synthesis and crystallization top

Refinement top

Structure description top

In recent years, Re and Tc radiopharmaceutical chemistry with the tricarbonyl precursor fac-[M(CO)₃(H₂O)₃]⁺ (M = ^99mTc, Re) has expanded continuously with the development of suitably derivatized novel ligand systems which efficiently displace the coordinating water molecules to produce complexes with high in vivo stability, favorable pharmacokinetic properties, and target tissue specificity (Mundwiler et al., 2004; Triantis et al., 2013; Jürgens et al., 2014; Alberto, 2012). In this article, we describe the crystal structure of a `2+1' tricarbonyl rhenium(I) complex, fac-[M(CO)₃(L)(NO—QA)], where L is triphenylarsane and NO—QA deprotonated quinaldic acid. This study is part of our ongoing research in the field of rhenium coordination compounds, particularly complexes bearing the fac-[Re(CO)₃]⁺ synthon, to develop new molecular radiopharmaceuticals. Related rhenium(I) tricarbonyl complexes have been reported by Schutte et al. (2011) and Manicum et al. (2015).

In the title compound, the Re^I cation is in a distorted octahedral environment (Fig. 1). The apical positions of the octahedron are occupied by the monodentate arsane ligand and one of the carbonyl groups (C34≡O32). The rhenium atom lies almost on the equatorial plane [displacement = 0.0459 (6) Å]. The five-membered ring defined by the metal ion and the chelating bidentate NO—QA anion is almost planar [maximum deviation of 0.078 (6) Å for atom N1]. One phenyl ring (C11–C16) of the triphenylarsane ligand exhibits intramolecular π–π interaction with the NO—QA ligand (Fig. 1), the distance from the centroid of the phenyl ring to the plane of the NO—QA ligand being 3.495 Å and the angle between the planes being 9.1°. In addition, intramolecular hydrogen bonds are established between the phenyl rings of the NO—QA ligand (C9—H9···O31) and between one of the phenyl rings of the triphenylarsane ligand (C24—H24···O1) with one carbonyl oxygen atom and one carboxylate oxygen atom respectively (Fig.1; Table 1). The Re—C≡O bond length in the apical position [Re—C34: 1.937 (12) Å] is longer than those in the equatorial plane [Re—C32 = 1.893 (8) Å and Re—C30 = 1.904 (9) Å] because of the trans influence of the triphenylarsane ligands, as expected (Coe & Glenwright, 2000; Otto & Johansson, 2002). Taking into account that this is the first structurally characterized Re^I triphenylarsane tricarbonyl complex, there are no other Re^I compound to compare with, but the measured Re—As distance of 2.5855 (10) Å is close to those given by Commons & Hoskins (1975) of 2.569–2.584 Å where the di(diphenylarsino)methane ligand is coordinating to an Re^I ion.

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Crystal Impact, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure and atom-labelling scheme of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity, except for those involved in intramolecular hydrogen bonding (dashed grey lines).
	Fig. 2. Weak intermolecular hydrogen bonds (C7—H7···O2 , C19—H19···O2 and C21—H21···O2) between neighbouring complexes indicated by dashed orange, yellow and turquoise lines, respectively. Intramolecular hydrogen bonds are not shown for clarity.
	Fig. 3. Chains of complexes, formed through C7—H7···O2 hydrogen bonds (dashed orange lines), parallel to the b axis.
	Fig. 4. The three-dimensional network of neighbouring chains formed through C19—H19···O2 and C21—H21···O2 hydrogen bonds (dashed orange and dashed turquoise lines, respectively) in a view along the b-axis direction.

fac-Tricarbonyl(quinoline-2-carboxylato-κ²N,O)(triphenylarsane-κAs)rhenium(I) top

Crystal data top

[Re(C₁₀H₆NO₂)(C₁₈H₁₅As)(CO)₃]	D_x = 1.821 Mg m⁻³
M_r = 748.61	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna2₁	Cell parameters from 17073 reflections
a = 18.1637 (3) Å	θ = 6.6–71.9°
b = 10.3463 (2) Å	µ = 10.40 mm⁻¹
c = 14.5322 (3) Å	T = 160 K
V = 2730.99 (9) Å³	Parallelepided, colorless
Z = 4	0.27 × 0.27 × 0.09 mm
F(000) = 1448

Data collection top

Rigaku R-AXIS SPIDER IPDS diffractometer	4655 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.052
θ scans	θ_max = 67.5°, θ_min = 7.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −20→15
T_min = 0.443, T_max = 1.00	k = −12→8
16386 measured reflections	l = −17→17
4768 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0343P)² + 0.6895P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.076	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 1.39 e Å⁻³
4768 reflections	Δρ_min = −1.50 e Å⁻³
352 parameters	Absolute structure: Flack x determined using 2096 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.019 (7)

Crystal data top

[Re(C₁₀H₆NO₂)(C₁₈H₁₅As)(CO)₃]	V = 2730.99 (9) Å³
M_r = 748.61	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 18.1637 (3) Å	µ = 10.40 mm⁻¹
b = 10.3463 (2) Å	T = 160 K
c = 14.5322 (3) Å	0.27 × 0.27 × 0.09 mm

Data collection top

Rigaku R-AXIS SPIDER IPDS diffractometer	4768 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	4655 reflections with I > 2σ(I)
T_min = 0.443, T_max = 1.00	R_int = 0.052
16386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 1.39 e Å⁻³
S = 1.05	Δρ_min = −1.50 e Å⁻³
4768 reflections	Absolute structure: Flack x determined using 2096 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
352 parameters	Absolute structure parameter: 0.019 (7)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Re	0.19141 (2)	0.85298 (3)	0.46794 (4)	0.01930 (12)
N1	0.2993 (4)	0.9464 (7)	0.4983 (4)	0.0229 (17)
O1	0.2681 (3)	0.6990 (5)	0.4781 (5)	0.0335 (14)
O2	0.3818 (4)	0.6409 (5)	0.5218 (5)	0.0385 (18)
C1	0.3333 (5)	0.7230 (9)	0.5073 (6)	0.029 (2)
C2	0.3522 (5)	0.8626 (7)	0.5221 (6)	0.0226 (19)
C3	0.4205 (5)	0.9006 (10)	0.5543 (7)	0.038 (2)
H3	0.4555	0.8369	0.5719	0.046*
C4	0.4377 (6)	1.0254 (10)	0.5610 (7)	0.040 (2)
H4	0.4844	1.0513	0.5840	0.048*
C5	0.3859 (6)	1.1180 (9)	0.5337 (7)	0.035 (2)
C6	0.4030 (7)	1.2520 (9)	0.5344 (7)	0.049 (3)
H6	0.4499	1.2802	0.5554	0.059*
C7	0.3516 (8)	1.3419 (9)	0.5048 (8)	0.054 (3)
H7	0.3624	1.4317	0.5079	0.064*
C8	0.2841 (6)	1.2999 (7)	0.4704 (9)	0.040 (2)
H8	0.2497	1.3621	0.4489	0.048*
C9	0.2659 (5)	1.1707 (7)	0.4666 (8)	0.034 (2)
H9	0.2200	1.1438	0.4419	0.040*
C10	0.3176 (5)	1.0772 (9)	0.5008 (6)	0.027 (2)
As	0.17369 (5)	0.81237 (9)	0.64209 (6)	0.0203 (2)
C11	0.2613 (5)	0.8487 (7)	0.7149 (6)	0.024 (2)
C12	0.3060 (4)	0.7508 (10)	0.7455 (6)	0.030 (2)
H12	0.2925	0.6633	0.7349	0.037*
C13	0.3712 (5)	0.7793 (10)	0.7920 (6)	0.039 (2)
H13	0.4019	0.7115	0.8137	0.047*
C14	0.3907 (6)	0.9064 (10)	0.8063 (7)	0.042 (3)
H14	0.4353	0.9260	0.8375	0.050*
C15	0.3456 (6)	1.0064 (11)	0.7755 (7)	0.042 (3)
H15	0.3586	1.0938	0.7873	0.050*
C16	0.2817 (5)	0.9779 (9)	0.7274 (6)	0.029 (2)
H16	0.2521	1.0454	0.7031	0.035*
C17	0.0961 (5)	0.9123 (8)	0.6992 (6)	0.0245 (19)
C18	0.1054 (5)	0.9746 (8)	0.7841 (5)	0.0279 (19)
H18	0.1501	0.9653	0.8173	0.033*
C19	0.0488 (5)	1.0500 (9)	0.8192 (6)	0.036 (2)
H19	0.0552	1.0959	0.8753	0.043*
C20	−0.0172 (5)	1.0575 (9)	0.7717 (7)	0.035 (2)
H20	−0.0562	1.1083	0.7960	0.042*
C21	−0.0273 (5)	0.9923 (8)	0.6896 (6)	0.029 (2)
H21	−0.0731	0.9970	0.6581	0.035*
C22	0.0299 (4)	0.9204 (8)	0.6543 (6)	0.0208 (17)
H22	0.0233	0.8757	0.5978	0.025*
C23	0.1471 (5)	0.6365 (7)	0.6769 (6)	0.027 (2)
C24	0.1601 (5)	0.5348 (8)	0.6156 (7)	0.033 (2)
H24	0.1829	0.5514	0.5580	0.040*
C25	0.1398 (5)	0.4106 (9)	0.6385 (8)	0.038 (2)
H25	0.1484	0.3411	0.5972	0.046*
C26	0.1067 (6)	0.3891 (9)	0.7223 (8)	0.043 (3)
H26	0.0927	0.3036	0.7384	0.052*
C27	0.0935 (5)	0.4873 (9)	0.7831 (7)	0.042 (2)
H27	0.0696	0.4697	0.8399	0.050*
C28	0.1148 (5)	0.6126 (9)	0.7618 (6)	0.032 (2)
H28	0.1075	0.6808	0.8046	0.039*
C30	0.1086 (5)	0.7452 (9)	0.4440 (5)	0.031 (2)
O30	0.0571 (4)	0.6812 (7)	0.4282 (5)	0.0404 (17)
C32	0.1253 (4)	0.9943 (7)	0.4725 (7)	0.0262 (17)
O31	0.0843 (3)	1.0805 (6)	0.4766 (6)	0.0421 (16)
C34	0.2037 (5)	0.8780 (10)	0.3367 (8)	0.033 (2)
O32	0.2073 (4)	0.8903 (9)	0.2592 (5)	0.047 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re	0.0220 (2)	0.01733 (18)	0.01854 (19)	−0.00165 (12)	0.00153 (18)	−0.00057 (19)
N1	0.026 (4)	0.022 (4)	0.020 (4)	0.003 (3)	0.002 (3)	0.001 (3)
O1	0.044 (4)	0.022 (3)	0.035 (3)	−0.004 (3)	0.000 (4)	−0.002 (3)
O2	0.044 (5)	0.026 (3)	0.046 (4)	0.018 (3)	0.004 (3)	0.004 (3)
C1	0.033 (6)	0.028 (5)	0.026 (4)	0.007 (4)	0.000 (4)	0.005 (4)
C2	0.022 (5)	0.025 (4)	0.020 (4)	0.004 (4)	−0.002 (4)	0.002 (3)
C3	0.026 (6)	0.045 (6)	0.044 (6)	0.003 (5)	−0.004 (5)	0.011 (5)
C4	0.033 (6)	0.041 (6)	0.046 (6)	−0.010 (5)	−0.005 (4)	−0.004 (5)
C5	0.040 (6)	0.030 (5)	0.035 (5)	−0.008 (5)	0.001 (4)	0.005 (4)
C6	0.066 (8)	0.033 (5)	0.050 (6)	−0.028 (6)	−0.007 (6)	−0.002 (5)
C7	0.084 (11)	0.029 (5)	0.048 (7)	−0.018 (6)	−0.004 (7)	0.003 (5)
C8	0.065 (7)	0.018 (4)	0.037 (5)	−0.001 (4)	0.011 (7)	0.001 (6)
C9	0.045 (6)	0.024 (4)	0.033 (4)	−0.005 (4)	0.005 (6)	0.006 (6)
C10	0.034 (6)	0.023 (4)	0.024 (4)	−0.013 (4)	0.007 (3)	0.003 (4)
As	0.0243 (5)	0.0170 (4)	0.0196 (4)	−0.0012 (4)	0.0007 (4)	0.0009 (4)
C11	0.027 (5)	0.024 (4)	0.021 (4)	0.001 (3)	0.004 (4)	0.004 (3)
C12	0.030 (6)	0.029 (5)	0.032 (5)	−0.003 (4)	−0.001 (4)	0.006 (4)
C13	0.032 (5)	0.054 (6)	0.032 (5)	0.007 (5)	−0.003 (4)	0.011 (5)
C14	0.024 (6)	0.056 (6)	0.045 (6)	−0.011 (5)	−0.010 (5)	−0.004 (6)
C15	0.038 (6)	0.050 (7)	0.038 (6)	−0.016 (6)	−0.008 (5)	−0.009 (5)
C16	0.033 (6)	0.026 (4)	0.028 (5)	−0.001 (4)	−0.003 (4)	−0.004 (4)
C17	0.027 (5)	0.021 (4)	0.026 (4)	−0.002 (4)	0.006 (4)	0.000 (4)
C18	0.026 (5)	0.039 (5)	0.019 (4)	−0.001 (4)	−0.002 (4)	−0.006 (4)
C19	0.041 (6)	0.036 (5)	0.030 (5)	−0.004 (4)	0.006 (4)	−0.015 (4)
C20	0.030 (6)	0.032 (5)	0.043 (6)	0.007 (5)	0.009 (4)	−0.004 (4)
C21	0.025 (5)	0.035 (5)	0.028 (5)	−0.004 (4)	0.000 (4)	0.005 (4)
C22	0.018 (4)	0.027 (4)	0.018 (4)	−0.008 (3)	0.003 (4)	−0.003 (4)
C23	0.022 (5)	0.026 (5)	0.031 (5)	−0.004 (4)	−0.002 (4)	0.002 (3)
C24	0.038 (6)	0.022 (5)	0.039 (6)	0.001 (4)	−0.002 (4)	−0.002 (4)
C25	0.035 (6)	0.023 (4)	0.057 (7)	−0.010 (4)	0.001 (6)	−0.002 (5)
C26	0.036 (6)	0.023 (4)	0.071 (8)	−0.011 (5)	−0.010 (6)	0.014 (5)
C27	0.037 (6)	0.047 (6)	0.041 (6)	−0.007 (5)	0.004 (5)	0.024 (5)
C28	0.028 (5)	0.033 (5)	0.037 (5)	0.001 (4)	−0.001 (4)	0.004 (4)
C30	0.040 (6)	0.032 (4)	0.021 (5)	−0.004 (4)	0.006 (4)	−0.002 (3)
O30	0.037 (4)	0.045 (4)	0.039 (4)	−0.022 (3)	0.003 (3)	−0.014 (3)
C32	0.032 (4)	0.027 (4)	0.019 (3)	−0.014 (4)	0.003 (4)	0.003 (5)
O31	0.039 (4)	0.038 (3)	0.049 (4)	0.017 (3)	0.009 (4)	0.012 (4)
C34	0.025 (5)	0.030 (5)	0.044 (7)	−0.005 (4)	−0.002 (5)	−0.002 (5)
O32	0.041 (4)	0.086 (6)	0.015 (4)	−0.004 (4)	0.008 (3)	0.009 (4)

Geometric parameters (Å, º) top

Re—C32	1.893 (8)	C13—C14	1.378 (14)
Re—C30	1.904 (9)	C13—H13	0.9500
Re—C34	1.937 (12)	C14—C15	1.394 (14)
Re—O1	2.122 (6)	C14—H14	0.9500
Re—N1	2.229 (7)	C15—C16	1.387 (13)
Re—As	2.5855 (10)	C15—H15	0.9500
N1—C2	1.339 (10)	C16—H16	0.9500
N1—C10	1.394 (11)	C17—C22	1.371 (11)
O1—C1	1.281 (11)	C17—C18	1.403 (11)
O2—C1	1.243 (10)	C18—C19	1.388 (12)
C1—C2	1.500 (11)	C18—H18	0.9500
C2—C3	1.383 (12)	C19—C20	1.386 (13)
C3—C4	1.333 (12)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.383 (12)
C4—C5	1.400 (13)	C20—H20	0.9500
C4—H4	0.9500	C21—C22	1.377 (11)
C5—C10	1.395 (13)	C21—H21	0.9500
C5—C6	1.422 (12)	C22—H22	0.9500
C6—C7	1.386 (17)	C23—C28	1.388 (12)
C6—H6	0.9500	C23—C24	1.399 (11)
C7—C8	1.394 (17)	C24—C25	1.377 (11)
C7—H7	0.9500	C24—H24	0.9500
C8—C9	1.378 (10)	C25—C26	1.376 (15)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.435 (13)	C26—C27	1.367 (14)
C9—H9	0.9500	C26—H26	0.9500
As—C17	1.935 (9)	C27—C28	1.389 (12)
As—C11	1.947 (10)	C27—H27	0.9500
As—C23	1.949 (8)	C28—H28	0.9500
C11—C12	1.373 (12)	C30—O30	1.169 (10)
C11—C16	1.399 (11)	C32—O31	1.163 (9)
C12—C13	1.395 (11)	C34—O32	1.136 (12)
C12—H12	0.9500

C32—Re—C30	87.6 (3)	C12—C11—As	121.1 (6)
C32—Re—C34	90.3 (4)	C16—C11—As	118.2 (6)
C30—Re—C34	89.4 (4)	C11—C12—C13	120.2 (9)
C32—Re—O1	173.8 (4)	C11—C12—H12	119.9
C30—Re—O1	95.2 (3)	C13—C12—H12	119.9
C34—Re—O1	95.3 (3)	C14—C13—C12	119.6 (9)
C32—Re—N1	102.5 (3)	C14—C13—H13	120.2
C30—Re—N1	169.8 (3)	C12—C13—H13	120.2
C34—Re—N1	92.0 (3)	C13—C14—C15	120.6 (9)
O1—Re—N1	74.6 (2)	C13—C14—H14	119.7
C32—Re—As	90.7 (3)	C15—C14—H14	119.7
C30—Re—As	89.1 (2)	C16—C15—C14	119.7 (9)
C34—Re—As	178.2 (3)	C16—C15—H15	120.1
O1—Re—As	83.80 (19)	C14—C15—H15	120.1
N1—Re—As	89.23 (17)	C15—C16—C11	119.4 (9)
C2—N1—C10	116.8 (7)	C15—C16—H16	120.3
C2—N1—Re	113.6 (6)	C11—C16—H16	120.3
C10—N1—Re	129.4 (6)	C22—C17—C18	119.7 (8)
C1—O1—Re	118.9 (5)	C22—C17—As	117.9 (6)
O2—C1—O1	125.4 (9)	C18—C17—As	122.4 (7)
O2—C1—C2	118.1 (9)	C19—C18—C17	119.5 (8)
O1—C1—C2	116.5 (8)	C19—C18—H18	120.2
N1—C2—C3	123.2 (8)	C17—C18—H18	120.2
N1—C2—C1	115.0 (8)	C20—C19—C18	119.3 (8)
C3—C2—C1	121.8 (8)	C20—C19—H19	120.4
C4—C3—C2	120.7 (9)	C18—C19—H19	120.4
C4—C3—H3	119.7	C21—C20—C19	121.2 (9)
C2—C3—H3	119.7	C21—C20—H20	119.4
C3—C4—C5	119.0 (9)	C19—C20—H20	119.4
C3—C4—H4	120.5	C22—C21—C20	119.0 (9)
C5—C4—H4	120.5	C22—C21—H21	120.5
C10—C5—C4	119.3 (9)	C20—C21—H21	120.5
C10—C5—C6	119.5 (10)	C17—C22—C21	121.2 (8)
C4—C5—C6	121.2 (10)	C17—C22—H22	119.4
C7—C6—C5	120.3 (11)	C21—C22—H22	119.4
C7—C6—H6	119.9	C28—C23—C24	120.2 (8)
C5—C6—H6	119.9	C28—C23—As	120.1 (6)
C6—C7—C8	119.7 (9)	C24—C23—As	119.7 (7)
C6—C7—H7	120.2	C25—C24—C23	120.2 (9)
C8—C7—H7	120.2	C25—C24—H24	119.9
C9—C8—C7	121.8 (10)	C23—C24—H24	119.9
C9—C8—H8	119.1	C26—C25—C24	118.8 (10)
C7—C8—H8	119.1	C26—C25—H25	120.6
C8—C9—C10	118.9 (9)	C24—C25—H25	120.6
C8—C9—H9	120.6	C27—C26—C25	121.9 (9)
C10—C9—H9	120.6	C27—C26—H26	119.1
N1—C10—C5	120.9 (9)	C25—C26—H26	119.1
N1—C10—C9	119.3 (8)	C26—C27—C28	120.1 (9)
C5—C10—C9	119.8 (8)	C26—C27—H27	120.0
C17—As—C11	105.0 (4)	C28—C27—H27	120.0
C17—As—C23	102.0 (4)	C23—C28—C27	118.8 (9)
C11—As—C23	104.0 (4)	C23—C28—H28	120.6
C17—As—Re	115.1 (3)	C27—C28—H28	120.6
C11—As—Re	113.5 (3)	O30—C30—Re	178.5 (8)
C23—As—Re	115.9 (3)	O31—C32—Re	179.0 (9)
C12—C11—C16	120.4 (9)	O32—C34—Re	176.5 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O31	0.95	2.60	3.431 (11)	146
C24—H24···O1	0.95	2.47	3.276 (12)	143
C7—H7···O2ⁱ	0.95	2.20	3.151 (11)	176
C21—H21···O2ⁱⁱ	0.95	2.57	3.251 (11)	128
C19—H19···O2ⁱⁱⁱ	0.95	2.46	3.337 (11)	153

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O31	0.95	2.60	3.431 (11)	146.4
C24—H24···O1	0.95	2.47	3.276 (12)	143.3
C7—H7···O2ⁱ	0.95	2.20	3.151 (11)	176.4
C21—H21···O2ⁱⁱ	0.95	2.57	3.251 (11)	128.4
C19—H19···O2ⁱⁱⁱ	0.95	2.46	3.337 (11)	153.3

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

Experimental details

Crystal data
Chemical formula	[Re(C₁₀H₆NO₂)(C₁₈H₁₅As)(CO)₃]
M_r	748.61
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	160
a, b, c (Å)	18.1637 (3), 10.3463 (2), 14.5322 (3)
V (Å³)	2730.99 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	10.40
Crystal size (mm)	0.27 × 0.27 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS SPIDER IPDS
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.443, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	16386, 4768, 4655
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.05
No. of reflections	4768
No. of parameters	352
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.39, −1.50
Absolute structure	Flack x determined using 2096 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	0.019 (7)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), DIAMOND (Crystal Impact, 2012), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Acknowledgements

CT would like to thank the State Scholarships Foundation (IKY) in Greece for financial support during his postgraduate studies in the framework of `IKY fellowships Excellence for postgraduate studies in Greece – Siemens program'.

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Volume 72| Part 2| February 2016| Pages 114-116

doi:10.1107/S2056989015024640

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