research communications
fac-tricarbonyl(quinoline-2-carboxylato-κ2N,O)(triphenylarsane-κAs)rhenium(I)
ofaInstitute 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
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.
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 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 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 (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 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.
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 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).
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 . 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).
details are summarized in Table 2Supporting information
CCDC reference: 1443806
10.1107/S2056989015024640/wm5246sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015024640/wm5246Isup2.hkl
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
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 (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 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
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).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 %).
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
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 (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 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
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).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 %).
detailsCrystal data, data collection and structure
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).Data collection: CrystalClear (Rigaku, 2005); cell
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).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. |
[Re(C10H6NO2)(C18H15As)(CO)3] | Dx = 1.821 Mg m−3 |
Mr = 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 |
Rigaku R-AXIS SPIDER IPDS diffractometer | 4655 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
θ scans | θmax = 67.5°, θmin = 7.2° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | h = −20→15 |
Tmin = 0.443, Tmax = 1.00 | k = −12→8 |
16386 measured reflections | l = −17→17 |
4768 independent reflections |
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(Fo2) + (0.0343P)2 + 0.6895P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.076 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 1.39 e Å−3 |
4768 reflections | Δρmin = −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) |
[Re(C10H6NO2)(C18H15As)(CO)3] | V = 2730.99 (9) Å3 |
Mr = 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 |
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 = 1.00 | Rint = 0.052 |
16386 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.076 | Δρmax = 1.39 e Å−3 |
S = 1.05 | Δρmin = −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 |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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) |
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. |
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] |
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) |
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) |
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 (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 |
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) |
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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