research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 114-116

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

CROSSMARK_Color_square_no_text.svg

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 ReI 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 ReI tri­phenyl­arsane tricarbonyl compound to be reported.

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[Mundwiler, S., Kündig, M., Ortner, K. & Alberto, R. (2004). Dalton Trans. pp. 1320.]; Tri­antis et al., 2013[Triantis, C., Tsotakos, T., Tsoukalas, C., Sagnou, M., Raptopoulou, C. P., Terzis, A., Psycharis, V., Pelecanou, M., Pirmettis, I. & Papadopoulos, M. (2013). Inorg. Chem. 52, 12995-13003.]; Jürgens et al., 2014[Jürgens, S., Herrmann, W. & Kühn, F. (2014). J. Organomet. Chem. 751, 83-89.]; Alberto, 2012[Alberto, R. (2012). Cosmos, 8, 83-101.]). 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[Schutte, M., Kemp, G., Visser, H. & Roodt, A. (2011). Inorg. Chem. 50, 12486-12498.]) and Manicum et al. (2015[Manicum, A.-L., Visser, H., Engelbrecht, I. & Roodt, A. (2015). Z. Kristallogr. 230, 150-152.]).

[Scheme 1]

2. Structural commentary

In the title compound, the ReI cation is in a distorted octa­hedral environment (Fig. 1[link]). 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 ππ inter­action with the NO-QA ligand (Fig. 1[link]), 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[link]). 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[Coe, J. B. & Glenwright, J. S. (2000). Coord. Chem. Rev. 203, 5-80.]; Otto & Johansson, 2002[Otto, S. & Johansson, H. M. (2002). Inorg. Chim. Acta, 329, 135-140.]). Taking into account that this is the first structurally characterized ReI tri­phenyl­arsane tricarbonyl complex, there are no other ReI compound to compare with, but the measured Re—As distance of 2.5855 (10) Å is close to those given by Commons & Hoskins (1975[Commons, C. J. & Hoskins, B. F. (1975). Aust. J. Chem. 28, 1201.]) of 2.569–2.584 Å where the di(di­phenyl­arsino)methane ligand is coordinating to an ReI ion.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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]
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[link] and Fig. 2[link]) 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[link]). 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[link]).

[Figure 2]
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]
Figure 3
Chains of complexes, formed through C7—H7⋯O2 hydrogen bonds (dashed orange lines), parallel to the b axis.
[Figure 4]
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[link]. C-bound H atoms were placed in idealized positions and refined using a riding model with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C).

Table 2
Experimental details

Crystal data
Chemical formula [Re(C10H6NO2)(C18H15As)(CO)3]
Mr 748.61
Crystal system, space group Orthorhombic, Pna21
Temperature (K) 160
a, b, c (Å) 18.1637 (3), 10.3463 (2), 14.5322 (3)
V3) 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[Rigaku (2005). CrystalClear. Rigaku MSC, The Woodlands, Texas, USA.])
Tmin, Tmax 0.443, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections 16386, 4768, 4655
Rint 0.052
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 1.39, −1.50
Absolute structure Flack x determined using 2096 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.019 (7)
Computer programs: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku MSC, The Woodlands, Texas, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), DIAMOND (Crystal Impact, 2012[Crystal Impact (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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 ReI 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 (C34O32). 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 ππ 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—CO 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 ReI tri­phenyl­arsane tri­carbonyl complex, there are no other ReI 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 ReI 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

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 %).

Refinement top

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 Uiso(H) = 1.2Ueq(C).

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 ReI 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 (C34O32). 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 ππ 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—CO 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 ReI tri­phenyl­arsane tri­carbonyl complex, there are no other ReI 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 ReI ion.

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

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 %).

Refinement details top

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 Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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).
[Figure 2] 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.
[Figure 3] Fig. 3. Chains of complexes, formed through C7—H7···O2 hydrogen bonds (dashed orange lines), parallel to the b axis.
[Figure 4] 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]Dx = 1.821 Mg m3
Mr = 748.61Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna21Cell parameters from 17073 reflections
a = 18.1637 (3) Åθ = 6.6–71.9°
b = 10.3463 (2) ŵ = 10.40 mm1
c = 14.5322 (3) ÅT = 160 K
V = 2730.99 (9) Å3Parallelepided, colorless
Z = 40.27 × 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 tubeRint = 0.052
θ scansθmax = 67.5°, θmin = 7.2°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
h = 2015
Tmin = 0.443, Tmax = 1.00k = 128
16386 measured reflectionsl = 1717
4768 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.6895P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max = 0.001
S = 1.05Δρmax = 1.39 e Å3
4768 reflectionsΔρmin = 1.50 e Å3
352 parametersAbsolute structure: Flack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.019 (7)
Crystal data top
[Re(C10H6NO2)(C18H15As)(CO)3]V = 2730.99 (9) Å3
Mr = 748.61Z = 4
Orthorhombic, Pna21Cu Kα radiation
a = 18.1637 (3) ŵ = 10.40 mm1
b = 10.3463 (2) ÅT = 160 K
c = 14.5322 (3) Å0.27 × 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)
Tmin = 0.443, Tmax = 1.00Rint = 0.052
16386 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.076Δρmax = 1.39 e Å3
S = 1.05Δρmin = 1.50 e Å3
4768 reflectionsAbsolute structure: Flack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
352 parametersAbsolute 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
xyzUiso*/Ueq
Re0.19141 (2)0.85298 (3)0.46794 (4)0.01930 (12)
N10.2993 (4)0.9464 (7)0.4983 (4)0.0229 (17)
O10.2681 (3)0.6990 (5)0.4781 (5)0.0335 (14)
O20.3818 (4)0.6409 (5)0.5218 (5)0.0385 (18)
C10.3333 (5)0.7230 (9)0.5073 (6)0.029 (2)
C20.3522 (5)0.8626 (7)0.5221 (6)0.0226 (19)
C30.4205 (5)0.9006 (10)0.5543 (7)0.038 (2)
H30.45550.83690.57190.046*
C40.4377 (6)1.0254 (10)0.5610 (7)0.040 (2)
H40.48441.05130.58400.048*
C50.3859 (6)1.1180 (9)0.5337 (7)0.035 (2)
C60.4030 (7)1.2520 (9)0.5344 (7)0.049 (3)
H60.44991.28020.55540.059*
C70.3516 (8)1.3419 (9)0.5048 (8)0.054 (3)
H70.36241.43170.50790.064*
C80.2841 (6)1.2999 (7)0.4704 (9)0.040 (2)
H80.24971.36210.44890.048*
C90.2659 (5)1.1707 (7)0.4666 (8)0.034 (2)
H90.22001.14380.44190.040*
C100.3176 (5)1.0772 (9)0.5008 (6)0.027 (2)
As0.17369 (5)0.81237 (9)0.64209 (6)0.0203 (2)
C110.2613 (5)0.8487 (7)0.7149 (6)0.024 (2)
C120.3060 (4)0.7508 (10)0.7455 (6)0.030 (2)
H120.29250.66330.73490.037*
C130.3712 (5)0.7793 (10)0.7920 (6)0.039 (2)
H130.40190.71150.81370.047*
C140.3907 (6)0.9064 (10)0.8063 (7)0.042 (3)
H140.43530.92600.83750.050*
C150.3456 (6)1.0064 (11)0.7755 (7)0.042 (3)
H150.35861.09380.78730.050*
C160.2817 (5)0.9779 (9)0.7274 (6)0.029 (2)
H160.25211.04540.70310.035*
C170.0961 (5)0.9123 (8)0.6992 (6)0.0245 (19)
C180.1054 (5)0.9746 (8)0.7841 (5)0.0279 (19)
H180.15010.96530.81730.033*
C190.0488 (5)1.0500 (9)0.8192 (6)0.036 (2)
H190.05521.09590.87530.043*
C200.0172 (5)1.0575 (9)0.7717 (7)0.035 (2)
H200.05621.10830.79600.042*
C210.0273 (5)0.9923 (8)0.6896 (6)0.029 (2)
H210.07310.99700.65810.035*
C220.0299 (4)0.9204 (8)0.6543 (6)0.0208 (17)
H220.02330.87570.59780.025*
C230.1471 (5)0.6365 (7)0.6769 (6)0.027 (2)
C240.1601 (5)0.5348 (8)0.6156 (7)0.033 (2)
H240.18290.55140.55800.040*
C250.1398 (5)0.4106 (9)0.6385 (8)0.038 (2)
H250.14840.34110.59720.046*
C260.1067 (6)0.3891 (9)0.7223 (8)0.043 (3)
H260.09270.30360.73840.052*
C270.0935 (5)0.4873 (9)0.7831 (7)0.042 (2)
H270.06960.46970.83990.050*
C280.1148 (5)0.6126 (9)0.7618 (6)0.032 (2)
H280.10750.68080.80460.039*
C300.1086 (5)0.7452 (9)0.4440 (5)0.031 (2)
O300.0571 (4)0.6812 (7)0.4282 (5)0.0404 (17)
C320.1253 (4)0.9943 (7)0.4725 (7)0.0262 (17)
O310.0843 (3)1.0805 (6)0.4766 (6)0.0421 (16)
C340.2037 (5)0.8780 (10)0.3367 (8)0.033 (2)
O320.2073 (4)0.8903 (9)0.2592 (5)0.047 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re0.0220 (2)0.01733 (18)0.01854 (19)0.00165 (12)0.00153 (18)0.00057 (19)
N10.026 (4)0.022 (4)0.020 (4)0.003 (3)0.002 (3)0.001 (3)
O10.044 (4)0.022 (3)0.035 (3)0.004 (3)0.000 (4)0.002 (3)
O20.044 (5)0.026 (3)0.046 (4)0.018 (3)0.004 (3)0.004 (3)
C10.033 (6)0.028 (5)0.026 (4)0.007 (4)0.000 (4)0.005 (4)
C20.022 (5)0.025 (4)0.020 (4)0.004 (4)0.002 (4)0.002 (3)
C30.026 (6)0.045 (6)0.044 (6)0.003 (5)0.004 (5)0.011 (5)
C40.033 (6)0.041 (6)0.046 (6)0.010 (5)0.005 (4)0.004 (5)
C50.040 (6)0.030 (5)0.035 (5)0.008 (5)0.001 (4)0.005 (4)
C60.066 (8)0.033 (5)0.050 (6)0.028 (6)0.007 (6)0.002 (5)
C70.084 (11)0.029 (5)0.048 (7)0.018 (6)0.004 (7)0.003 (5)
C80.065 (7)0.018 (4)0.037 (5)0.001 (4)0.011 (7)0.001 (6)
C90.045 (6)0.024 (4)0.033 (4)0.005 (4)0.005 (6)0.006 (6)
C100.034 (6)0.023 (4)0.024 (4)0.013 (4)0.007 (3)0.003 (4)
As0.0243 (5)0.0170 (4)0.0196 (4)0.0012 (4)0.0007 (4)0.0009 (4)
C110.027 (5)0.024 (4)0.021 (4)0.001 (3)0.004 (4)0.004 (3)
C120.030 (6)0.029 (5)0.032 (5)0.003 (4)0.001 (4)0.006 (4)
C130.032 (5)0.054 (6)0.032 (5)0.007 (5)0.003 (4)0.011 (5)
C140.024 (6)0.056 (6)0.045 (6)0.011 (5)0.010 (5)0.004 (6)
C150.038 (6)0.050 (7)0.038 (6)0.016 (6)0.008 (5)0.009 (5)
C160.033 (6)0.026 (4)0.028 (5)0.001 (4)0.003 (4)0.004 (4)
C170.027 (5)0.021 (4)0.026 (4)0.002 (4)0.006 (4)0.000 (4)
C180.026 (5)0.039 (5)0.019 (4)0.001 (4)0.002 (4)0.006 (4)
C190.041 (6)0.036 (5)0.030 (5)0.004 (4)0.006 (4)0.015 (4)
C200.030 (6)0.032 (5)0.043 (6)0.007 (5)0.009 (4)0.004 (4)
C210.025 (5)0.035 (5)0.028 (5)0.004 (4)0.000 (4)0.005 (4)
C220.018 (4)0.027 (4)0.018 (4)0.008 (3)0.003 (4)0.003 (4)
C230.022 (5)0.026 (5)0.031 (5)0.004 (4)0.002 (4)0.002 (3)
C240.038 (6)0.022 (5)0.039 (6)0.001 (4)0.002 (4)0.002 (4)
C250.035 (6)0.023 (4)0.057 (7)0.010 (4)0.001 (6)0.002 (5)
C260.036 (6)0.023 (4)0.071 (8)0.011 (5)0.010 (6)0.014 (5)
C270.037 (6)0.047 (6)0.041 (6)0.007 (5)0.004 (5)0.024 (5)
C280.028 (5)0.033 (5)0.037 (5)0.001 (4)0.001 (4)0.004 (4)
C300.040 (6)0.032 (4)0.021 (5)0.004 (4)0.006 (4)0.002 (3)
O300.037 (4)0.045 (4)0.039 (4)0.022 (3)0.003 (3)0.014 (3)
C320.032 (4)0.027 (4)0.019 (3)0.014 (4)0.003 (4)0.003 (5)
O310.039 (4)0.038 (3)0.049 (4)0.017 (3)0.009 (4)0.012 (4)
C340.025 (5)0.030 (5)0.044 (7)0.005 (4)0.002 (5)0.002 (5)
O320.041 (4)0.086 (6)0.015 (4)0.004 (4)0.008 (3)0.009 (4)
Geometric parameters (Å, º) top
Re—C321.893 (8)C13—C141.378 (14)
Re—C301.904 (9)C13—H130.9500
Re—C341.937 (12)C14—C151.394 (14)
Re—O12.122 (6)C14—H140.9500
Re—N12.229 (7)C15—C161.387 (13)
Re—As2.5855 (10)C15—H150.9500
N1—C21.339 (10)C16—H160.9500
N1—C101.394 (11)C17—C221.371 (11)
O1—C11.281 (11)C17—C181.403 (11)
O2—C11.243 (10)C18—C191.388 (12)
C1—C21.500 (11)C18—H180.9500
C2—C31.383 (12)C19—C201.386 (13)
C3—C41.333 (12)C19—H190.9500
C3—H30.9500C20—C211.383 (12)
C4—C51.400 (13)C20—H200.9500
C4—H40.9500C21—C221.377 (11)
C5—C101.395 (13)C21—H210.9500
C5—C61.422 (12)C22—H220.9500
C6—C71.386 (17)C23—C281.388 (12)
C6—H60.9500C23—C241.399 (11)
C7—C81.394 (17)C24—C251.377 (11)
C7—H70.9500C24—H240.9500
C8—C91.378 (10)C25—C261.376 (15)
C8—H80.9500C25—H250.9500
C9—C101.435 (13)C26—C271.367 (14)
C9—H90.9500C26—H260.9500
As—C171.935 (9)C27—C281.389 (12)
As—C111.947 (10)C27—H270.9500
As—C231.949 (8)C28—H280.9500
C11—C121.373 (12)C30—O301.169 (10)
C11—C161.399 (11)C32—O311.163 (9)
C12—C131.395 (11)C34—O321.136 (12)
C12—H120.9500
C32—Re—C3087.6 (3)C12—C11—As121.1 (6)
C32—Re—C3490.3 (4)C16—C11—As118.2 (6)
C30—Re—C3489.4 (4)C11—C12—C13120.2 (9)
C32—Re—O1173.8 (4)C11—C12—H12119.9
C30—Re—O195.2 (3)C13—C12—H12119.9
C34—Re—O195.3 (3)C14—C13—C12119.6 (9)
C32—Re—N1102.5 (3)C14—C13—H13120.2
C30—Re—N1169.8 (3)C12—C13—H13120.2
C34—Re—N192.0 (3)C13—C14—C15120.6 (9)
O1—Re—N174.6 (2)C13—C14—H14119.7
C32—Re—As90.7 (3)C15—C14—H14119.7
C30—Re—As89.1 (2)C16—C15—C14119.7 (9)
C34—Re—As178.2 (3)C16—C15—H15120.1
O1—Re—As83.80 (19)C14—C15—H15120.1
N1—Re—As89.23 (17)C15—C16—C11119.4 (9)
C2—N1—C10116.8 (7)C15—C16—H16120.3
C2—N1—Re113.6 (6)C11—C16—H16120.3
C10—N1—Re129.4 (6)C22—C17—C18119.7 (8)
C1—O1—Re118.9 (5)C22—C17—As117.9 (6)
O2—C1—O1125.4 (9)C18—C17—As122.4 (7)
O2—C1—C2118.1 (9)C19—C18—C17119.5 (8)
O1—C1—C2116.5 (8)C19—C18—H18120.2
N1—C2—C3123.2 (8)C17—C18—H18120.2
N1—C2—C1115.0 (8)C20—C19—C18119.3 (8)
C3—C2—C1121.8 (8)C20—C19—H19120.4
C4—C3—C2120.7 (9)C18—C19—H19120.4
C4—C3—H3119.7C21—C20—C19121.2 (9)
C2—C3—H3119.7C21—C20—H20119.4
C3—C4—C5119.0 (9)C19—C20—H20119.4
C3—C4—H4120.5C22—C21—C20119.0 (9)
C5—C4—H4120.5C22—C21—H21120.5
C10—C5—C4119.3 (9)C20—C21—H21120.5
C10—C5—C6119.5 (10)C17—C22—C21121.2 (8)
C4—C5—C6121.2 (10)C17—C22—H22119.4
C7—C6—C5120.3 (11)C21—C22—H22119.4
C7—C6—H6119.9C28—C23—C24120.2 (8)
C5—C6—H6119.9C28—C23—As120.1 (6)
C6—C7—C8119.7 (9)C24—C23—As119.7 (7)
C6—C7—H7120.2C25—C24—C23120.2 (9)
C8—C7—H7120.2C25—C24—H24119.9
C9—C8—C7121.8 (10)C23—C24—H24119.9
C9—C8—H8119.1C26—C25—C24118.8 (10)
C7—C8—H8119.1C26—C25—H25120.6
C8—C9—C10118.9 (9)C24—C25—H25120.6
C8—C9—H9120.6C27—C26—C25121.9 (9)
C10—C9—H9120.6C27—C26—H26119.1
N1—C10—C5120.9 (9)C25—C26—H26119.1
N1—C10—C9119.3 (8)C26—C27—C28120.1 (9)
C5—C10—C9119.8 (8)C26—C27—H27120.0
C17—As—C11105.0 (4)C28—C27—H27120.0
C17—As—C23102.0 (4)C23—C28—C27118.8 (9)
C11—As—C23104.0 (4)C23—C28—H28120.6
C17—As—Re115.1 (3)C27—C28—H28120.6
C11—As—Re113.5 (3)O30—C30—Re178.5 (8)
C23—As—Re115.9 (3)O31—C32—Re179.0 (9)
C12—C11—C16120.4 (9)O32—C34—Re176.5 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O310.952.603.431 (11)146
C24—H24···O10.952.473.276 (12)143
C7—H7···O2i0.952.203.151 (11)176
C21—H21···O2ii0.952.573.251 (11)128
C19—H19···O2iii0.952.463.337 (11)153
Symmetry codes: (i) x, y+1, z; (ii) x1/2, y+3/2, z; (iii) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O310.952.603.431 (11)146.4
C24—H24···O10.952.473.276 (12)143.3
C7—H7···O2i0.952.203.151 (11)176.4
C21—H21···O2ii0.952.573.251 (11)128.4
C19—H19···O2iii0.952.463.337 (11)153.3
Symmetry codes: (i) x, y+1, z; (ii) x1/2, 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]
Mr748.61
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)160
a, b, c (Å)18.1637 (3), 10.3463 (2), 14.5322 (3)
V3)2730.99 (9)
Z4
Radiation typeCu Kα
µ (mm1)10.40
Crystal size (mm)0.27 × 0.27 × 0.09
Data collection
DiffractometerRigaku R-AXIS SPIDER IPDS
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.443, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
16386, 4768, 4655
Rint0.052
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.076, 1.05
No. of reflections4768
No. of parameters352
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.39, 1.50
Absolute structureFlack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.019 (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'.

References

First citationAlberto, R. (2012). Cosmos, 8, 83–101.  CrossRef Google Scholar
First citationCoe, J. B. & Glenwright, J. S. (2000). Coord. Chem. Rev. 203, 5–80.  Web of Science CrossRef CAS Google Scholar
First citationCommons, C. J. & Hoskins, B. F. (1975). Aust. J. Chem. 28, 1201.  CSD CrossRef Google Scholar
First citationCrystal Impact (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationJürgens, S., Herrmann, W. & Kühn, F. (2014). J. Organomet. Chem. 751, 83–89.  Google Scholar
First citationManicum, A.-L., Visser, H., Engelbrecht, I. & Roodt, A. (2015). Z. Kristallogr. 230, 150–152.  CAS Google Scholar
First citationMundwiler, S., Kündig, M., Ortner, K. & Alberto, R. (2004). Dalton Trans. pp. 1320.  Google Scholar
First citationOtto, S. & Johansson, H. M. (2002). Inorg. Chim. Acta, 329, 135–140.  Web of Science CSD CrossRef CAS Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSchutte, M., Kemp, G., Visser, H. & Roodt, A. (2011). Inorg. Chem. 50, 12486–12498.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTriantis, C., Tsotakos, T., Tsoukalas, C., Sagnou, M., Raptopoulou, C. P., Terzis, A., Psycharis, V., Pelecanou, M., Pirmettis, I. & Papadopoulos, M. (2013). Inorg. Chem. 52, 12995–13003.  Web of Science CSD CrossRef CAS PubMed Google Scholar

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ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 114-116
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