metal-organic compounds
An acetonitrile solvatomorph of dichlorido(1,10-phenanthroline-5,6-dione)platinum(II)
aDepartment of Chemistry and Biochemistry, 1001 E. University Ave., Georgetown, Texas 78626, USA, and bDepartment of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA
*Correspondence e-mail: rawji@southwestern.edu
In the title complex, [PtCl2(C12H6N2O2)]·CH3CN, the PtII atom lies in a slightly distorted square-planar arrangement defined by an N2Cl2 donor set. In the packed structure, columns of complex moieties are stacked such that the neighboring units are oriented at 180° and laterally displaced with respect to each other. This prevents any overlap of the phenanthroline rings and thus there is no possibility of any π–π interactions between aromatic rings.
CCDC reference: 974560
Related literature
For condensation of the free and complexed phendione ligand with primary ); MacDonnell & Bodige (1996); Moucheron et al. (1997); Westerlund et al. (2005); Williams et al. (2012). For use of the ligand in the construction of multinuclear homo- and heterometallic complexes as well as dendritic polynuclear metal structures, see: Fox et al. (1991); MacDonnell & Bodige (1996); Paw & Eisenberg (1997); Calderazzo et al. (1999); Campagna et al. (1999); Calucci et al. (2006). For antimicrobial activity of the free ligand and the title complex, see: Roy et al. (2008). For previous structural studies related to the title complex, see: Granger et al. (2005); Okamura et al. (2006); Roy et al. (2008). For synthesis of Pt(DMSO)2Cl2, see: Romeo & Scolaro (1998).
see: Dickerson & Summers (1970Experimental
Crystal data
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Data collection: COLLECT (Nonius, 1998); cell COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: XP in SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 974560
https://doi.org/10.1107/S160053681303256X/mw2118sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681303256X/mw2118Isup2.hkl
1,10-phenanthroline-5,6-dione (phendione), a versatile electroactive ligand with dual functionalities (diquinoid and diimine), has been widely used in condensation with primary
either as a free phendione entity (Dickerson & Summers, 1970) or one coordinated to a metal center (MacDonnell & Bodige, 1996; Moucheron et al., 1997; Westerlund et al., 2005; Williams et al., 2012). Because of its dual functionalities, the phendione ligand has been used as a bridging ligand in homo- and heterometallic multinuclear complexes and polymetallic dendritic structures (Fox et al., 1991; MacDonnell & Bodige, 1996; Paw & Eisenberg, 1997; Calderazzo et al., 1999; Campagna et al., 1999; Calucci et al., 2006). The antimicrobial properties of this complex and the free ligand have also been investigated (Roy et al., 2008). In our studies, this ligand and the title complex have been used in the synthesis of metallointercalators of DNA.Three structural studies of dichloro(phendione)platinum(II) have been reported (Granger et al., 2005; Okamura et al., 2006; Roy et al., 2008). In all three studies, the complex was obtained as a DMSO solvate in the Cc
Two of these studies appear to be preliminary (Granger et al., 2005; Okamura et al., 2006) and the structural data were not submitted to the Cambridge Structural Database (CSD). The third study is thorough and its deposited data (CCDC 678530) are available for comparison (Roy et al., 2008). The structure reported here is an acetonitrile solvate belonging to a different monoclinic P21/c, resulting in a very different three dimensional packing arrangement compared to that in the reported study.The title complex is essentially planar with three of the four bond angles about the Pt atom deviating slightly from the idealized square planar geometry. The N12—Pt1—N1 angle is significantly reduced to ~81° due to the constraints of the phendione ligand and two of the remaining bond angles are ~95° (Fig. 1). The contains four molecules each of the complex and the solvent, acetonitrile. Intermolecular interactions are responsible for the observed three dimensional array which may be described as consisting of zigzagging columns of stacked complex moieties, oriented 180° and laterally displaced with respect to each other. The separation between the stacked moieties alternates between 3.360 Å and 3.364 Å but due to the relative orientation of the stacked units, π-π stacking is not possible. The solvent molecules lie between the columns in the space created by the zigzagging (Fig. 2).
The three dimensional array of the title complex is clearly different from that of the reported structure (Roy et al., 2008). A major contributing factor to the different packing arrangements observed in the two studies is the relative orientation of the stacked complex moieties with respect to each other, 180° (current study) versus ~120° (reported (Roy et al., 2008)). The 120° orientation allows a partial overlap of the end rings of the stacked phendione ligands thereby increasing the potential for π-π interaction. Therefore, the structural study reported here is consistent with a solvate polymorph of [Pt(phendione)Cl2] in which acetonitrile as the solvent leads to a different packing arrangement than in the DMSO solvate structure.
The phendione ligand, K2PtCl4, and other reagents used in the syntheses were purchased from Sigma-Aldrich. [Pt(DMSO)2Cl2] was prepared from K2PtCl4 and DMSO according to the literature (Romeo & Scolaro, 1998). The title complex was synthesized by adding the solid ligand in a 1:1 molar ratio to a stirred acetonitrile solution of [Pt(DMSO)2Cl2] at maintained at 343 K. The pale yellow mixture was kept stirred at this temperature for ~2 hours while replenishing the solvent as necessary. During this time, as the color darkened, orange needles began to precipitate. The mixture was removed from heat and left covered at room temperature for slow crystallization. Good quality light orange needle-shaped crystals suitable for a were obtained after ~6 hours. Yield: 40%.
1,10-phenanthroline-5,6-dione (phendione), a versatile electroactive ligand with dual functionalities (diquinoid and diimine), has been widely used in condensation with primary
either as a free phendione entity (Dickerson & Summers, 1970) or one coordinated to a metal center (MacDonnell & Bodige, 1996; Moucheron et al., 1997; Westerlund et al., 2005; Williams et al., 2012). Because of its dual functionalities, the phendione ligand has been used as a bridging ligand in homo- and heterometallic multinuclear complexes and polymetallic dendritic structures (Fox et al., 1991; MacDonnell & Bodige, 1996; Paw & Eisenberg, 1997; Calderazzo et al., 1999; Campagna et al., 1999; Calucci et al., 2006). The antimicrobial properties of this complex and the free ligand have also been investigated (Roy et al., 2008). In our studies, this ligand and the title complex have been used in the synthesis of metallointercalators of DNA.Three structural studies of dichloro(phendione)platinum(II) have been reported (Granger et al., 2005; Okamura et al., 2006; Roy et al., 2008). In all three studies, the complex was obtained as a DMSO solvate in the Cc
Two of these studies appear to be preliminary (Granger et al., 2005; Okamura et al., 2006) and the structural data were not submitted to the Cambridge Structural Database (CSD). The third study is thorough and its deposited data (CCDC 678530) are available for comparison (Roy et al., 2008). The structure reported here is an acetonitrile solvate belonging to a different monoclinic P21/c, resulting in a very different three dimensional packing arrangement compared to that in the reported study.The title complex is essentially planar with three of the four bond angles about the Pt atom deviating slightly from the idealized square planar geometry. The N12—Pt1—N1 angle is significantly reduced to ~81° due to the constraints of the phendione ligand and two of the remaining bond angles are ~95° (Fig. 1). The contains four molecules each of the complex and the solvent, acetonitrile. Intermolecular interactions are responsible for the observed three dimensional array which may be described as consisting of zigzagging columns of stacked complex moieties, oriented 180° and laterally displaced with respect to each other. The separation between the stacked moieties alternates between 3.360 Å and 3.364 Å but due to the relative orientation of the stacked units, π-π stacking is not possible. The solvent molecules lie between the columns in the space created by the zigzagging (Fig. 2).
The three dimensional array of the title complex is clearly different from that of the reported structure (Roy et al., 2008). A major contributing factor to the different packing arrangements observed in the two studies is the relative orientation of the stacked complex moieties with respect to each other, 180° (current study) versus ~120° (reported (Roy et al., 2008)). The 120° orientation allows a partial overlap of the end rings of the stacked phendione ligands thereby increasing the potential for π-π interaction. Therefore, the structural study reported here is consistent with a solvate polymorph of [Pt(phendione)Cl2] in which acetonitrile as the solvent leads to a different packing arrangement than in the DMSO solvate structure.
For condensation of the free and complexed phendione ligand with primary
see: Dickerson & Summers (1970); MacDonnell & Bodige (1996); Moucheron et al. (1997); Westerlund et al. (2005); Williams et al. (2012). For use of the ligand in the construction of multinuclear homo- and heterometallic complexes as well as dendritic polynuclear metal structures, see: Fox et al. (1991); MacDonnell & Bodige (1996); Paw & Eisenberg (1997); Calderazzo et al. (1999); Campagna et al. (1999); Calucci et al. (2006). For antimicrobial activity of the free ligand and the title complex, see: Roy et al. (2008). For previous structural studies related to the title complex, see: Granger et al. (2005); Okamura et al. (2006); Roy et al. (2008). For synthesis of Pt(DMSO)2Cl2, see: Romeo & Scolaro (1998).The phendione ligand, K2PtCl4, and other reagents used in the syntheses were purchased from Sigma-Aldrich. [Pt(DMSO)2Cl2] was prepared from K2PtCl4 and DMSO according to the literature (Romeo & Scolaro, 1998). The title complex was synthesized by adding the solid ligand in a 1:1 molar ratio to a stirred acetonitrile solution of [Pt(DMSO)2Cl2] at maintained at 343 K. The pale yellow mixture was kept stirred at this temperature for ~2 hours while replenishing the solvent as necessary. During this time, as the color darkened, orange needles began to precipitate. The mixture was removed from heat and left covered at room temperature for slow crystallization. Good quality light orange needle-shaped crystals suitable for a were obtained after ~6 hours. Yield: 40%.
detailsThe H atoms were placed in idealized positions (aromatic C—H distances of 0.93 Å and methyl C—H distances of 0.96 Å) with displacement parameters Uiso(H)set to 1.2Ueq(C) for aromatic and 1.5Ueq(C) for methyl protons.
Data collection: COLLECT (Nonius, 1998); cell
COLLECT (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: XP SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. An ORTEP diagram of the title complex showing 50% probability displacement elipsoids. | |
Fig. 2. A packing diagram of the title complex viewed down the c axis. |
[PtCl2(C12H6N2O2)]·C2H3N | F(000) = 968 |
Mr = 517.23 | Dx = 2.335 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7285 (2) Å | Cell parameters from 3185 reflections |
b = 22.6380 (6) Å | θ = 1.0–27.5° |
c = 9.7561 (3) Å | µ = 9.91 mm−1 |
β = 98.0740 (17)° | T = 298 K |
V = 1471.32 (7) Å3 | Needle, yellow |
Z = 4 | 0.40 × 0.06 × 0.05 mm |
Nonius KappaCCD diffractometer | 2837 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.081 |
φ and ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: gaussian (XPREP in SHELXL/PC; Sheldrick, 2008) | h = −7→8 |
Tmin = 0.174, Tmax = 0.629 | k = −29→26 |
11801 measured reflections | l = −12→9 |
3345 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0216P)2 + 7.4291P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.002 |
3345 reflections | Δρmax = 1.48 e Å−3 |
201 parameters | Δρmin = −1.30 e Å−3 |
0 restraints | Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0038 (4) |
[PtCl2(C12H6N2O2)]·C2H3N | V = 1471.32 (7) Å3 |
Mr = 517.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.7285 (2) Å | µ = 9.91 mm−1 |
b = 22.6380 (6) Å | T = 298 K |
c = 9.7561 (3) Å | 0.40 × 0.06 × 0.05 mm |
β = 98.0740 (17)° |
Nonius KappaCCD diffractometer | 3345 independent reflections |
Absorption correction: gaussian (XPREP in SHELXL/PC; Sheldrick, 2008) | 2837 reflections with I > 2σ(I) |
Tmin = 0.174, Tmax = 0.629 | Rint = 0.081 |
11801 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.16 | Δρmax = 1.48 e Å−3 |
3345 reflections | Δρmin = −1.30 e Å−3 |
201 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Pt1 | 0.22275 (4) | 0.538338 (12) | 0.35597 (3) | 0.03226 (13) | |
Cl1 | 0.2456 (3) | 0.63727 (10) | 0.4031 (2) | 0.0535 (5) | |
Cl2 | 0.1736 (3) | 0.55973 (11) | 0.12469 (18) | 0.0490 (5) | |
O1 | 0.2795 (12) | 0.3386 (4) | 0.8277 (7) | 0.078 (2) | |
O2 | 0.2372 (13) | 0.2739 (4) | 0.5941 (9) | 0.088 (2) | |
N1 | 0.2643 (8) | 0.5130 (3) | 0.5574 (5) | 0.0332 (13) | |
C2 | 0.2906 (10) | 0.5475 (4) | 0.6672 (8) | 0.0413 (18) | |
H2A | 0.2927 | 0.5882 | 0.6548 | 0.050* | |
C3 | 0.3157 (11) | 0.5248 (4) | 0.8018 (8) | 0.047 (2) | |
H3A | 0.3346 | 0.5501 | 0.8777 | 0.057* | |
C4 | 0.3120 (12) | 0.4655 (4) | 0.8204 (8) | 0.050 (2) | |
H4A | 0.3290 | 0.4496 | 0.9093 | 0.060* | |
C5 | 0.2831 (11) | 0.4291 (4) | 0.7071 (8) | 0.0437 (19) | |
C6 | 0.2705 (13) | 0.3630 (5) | 0.7205 (10) | 0.060 (3) | |
C7 | 0.2476 (13) | 0.3264 (5) | 0.5856 (10) | 0.055 (2) | |
C8 | 0.2270 (12) | 0.3572 (4) | 0.4480 (9) | 0.0442 (18) | |
C9 | 0.2042 (13) | 0.3274 (4) | 0.3234 (9) | 0.055 (2) | |
H9A | 0.2025 | 0.2864 | 0.3205 | 0.066* | |
C10 | 0.1843 (13) | 0.3600 (5) | 0.2043 (9) | 0.056 (2) | |
H10A | 0.1715 | 0.3409 | 0.1192 | 0.067* | |
C11 | 0.1828 (11) | 0.4203 (4) | 0.2087 (8) | 0.0428 (18) | |
H11A | 0.1639 | 0.4414 | 0.1262 | 0.051* | |
N12 | 0.2080 (8) | 0.4498 (3) | 0.3291 (6) | 0.0339 (13) | |
C13 | 0.2300 (10) | 0.4186 (4) | 0.4489 (7) | 0.0342 (15) | |
C14 | 0.2592 (11) | 0.4543 (3) | 0.5756 (7) | 0.0335 (16) | |
N1A | 0.328 (2) | 0.6730 (6) | −0.1587 (14) | 0.109 (4) | |
C2A | 0.2973 (18) | 0.6945 (6) | −0.0552 (13) | 0.076 (3) | |
C3A | 0.2662 (19) | 0.7226 (6) | 0.0677 (12) | 0.085 (3) | |
H3A1 | 0.3414 | 0.7588 | 0.0775 | 0.127* | |
H3A2 | 0.3099 | 0.6972 | 0.1448 | 0.127* | |
H3A3 | 0.1259 | 0.7312 | 0.0650 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1 | 0.03263 (17) | 0.03434 (19) | 0.03048 (17) | −0.00009 (12) | 0.00674 (10) | −0.00010 (11) |
Cl1 | 0.0700 (14) | 0.0367 (11) | 0.0542 (11) | −0.0022 (10) | 0.0102 (9) | −0.0047 (9) |
Cl2 | 0.0597 (12) | 0.0558 (13) | 0.0317 (9) | −0.0014 (10) | 0.0069 (8) | 0.0063 (8) |
O1 | 0.095 (5) | 0.081 (6) | 0.060 (4) | 0.013 (4) | 0.015 (4) | 0.039 (4) |
O2 | 0.127 (7) | 0.042 (5) | 0.094 (6) | 0.005 (4) | 0.018 (5) | 0.027 (4) |
N1 | 0.024 (3) | 0.048 (4) | 0.029 (3) | −0.003 (3) | 0.006 (2) | −0.001 (3) |
C2 | 0.033 (4) | 0.051 (5) | 0.041 (4) | −0.002 (3) | 0.010 (3) | −0.007 (3) |
C3 | 0.041 (4) | 0.071 (7) | 0.030 (4) | 0.003 (4) | 0.009 (3) | −0.010 (4) |
C4 | 0.040 (4) | 0.076 (7) | 0.034 (4) | 0.006 (4) | 0.006 (3) | 0.009 (4) |
C5 | 0.031 (4) | 0.062 (6) | 0.039 (4) | 0.005 (4) | 0.008 (3) | 0.007 (4) |
C6 | 0.050 (5) | 0.074 (7) | 0.057 (5) | 0.012 (5) | 0.009 (4) | 0.024 (5) |
C7 | 0.056 (5) | 0.050 (6) | 0.060 (5) | 0.007 (4) | 0.017 (4) | 0.018 (4) |
C8 | 0.045 (4) | 0.030 (4) | 0.058 (5) | 0.009 (3) | 0.009 (3) | 0.008 (3) |
C9 | 0.068 (6) | 0.036 (5) | 0.063 (5) | −0.002 (4) | 0.012 (4) | −0.010 (4) |
C10 | 0.061 (5) | 0.056 (6) | 0.051 (5) | −0.003 (5) | 0.010 (4) | −0.015 (4) |
C11 | 0.042 (4) | 0.044 (5) | 0.042 (4) | −0.005 (4) | 0.007 (3) | −0.009 (3) |
N12 | 0.035 (3) | 0.037 (4) | 0.031 (3) | 0.001 (3) | 0.007 (2) | −0.001 (2) |
C13 | 0.028 (3) | 0.040 (4) | 0.035 (3) | 0.002 (3) | 0.005 (3) | −0.003 (3) |
C14 | 0.033 (3) | 0.037 (4) | 0.033 (3) | 0.000 (3) | 0.005 (3) | 0.001 (3) |
N1A | 0.131 (10) | 0.094 (10) | 0.105 (9) | −0.019 (8) | 0.023 (7) | −0.019 (7) |
C2A | 0.090 (8) | 0.056 (7) | 0.086 (8) | −0.001 (6) | 0.021 (6) | 0.003 (6) |
C3A | 0.106 (9) | 0.074 (9) | 0.076 (8) | 0.006 (7) | 0.019 (6) | 0.010 (6) |
Pt1—N12 | 2.022 (7) | C7—C8 | 1.503 (12) |
Pt1—N1 | 2.028 (5) | C8—C9 | 1.380 (12) |
Pt1—Cl2 | 2.2860 (18) | C8—C13 | 1.389 (11) |
Pt1—Cl1 | 2.287 (2) | C9—C10 | 1.367 (13) |
O1—C6 | 1.177 (11) | C9—H9A | 0.9300 |
O2—C7 | 1.192 (13) | C10—C11 | 1.365 (13) |
N1—C2 | 1.318 (10) | C10—H10A | 0.9300 |
N1—C14 | 1.341 (10) | C11—N12 | 1.341 (9) |
C2—C3 | 1.398 (11) | C11—H11A | 0.9300 |
C2—H2A | 0.9300 | N12—C13 | 1.356 (9) |
C3—C4 | 1.356 (13) | C13—C14 | 1.466 (10) |
C3—H3A | 0.9300 | N1A—C2A | 1.166 (16) |
C4—C5 | 1.370 (12) | C2A—C3A | 1.399 (17) |
C4—H4A | 0.9300 | C3A—H3A1 | 0.9600 |
C5—C14 | 1.395 (11) | C3A—H3A2 | 0.9600 |
C5—C6 | 1.506 (14) | C3A—H3A3 | 0.9600 |
C6—C7 | 1.545 (15) | ||
N12—Pt1—N1 | 81.0 (2) | C9—C8—C7 | 123.0 (8) |
N12—Pt1—Cl2 | 94.83 (17) | C13—C8—C7 | 117.4 (8) |
N1—Pt1—Cl2 | 175.8 (2) | C10—C9—C8 | 118.1 (9) |
N12—Pt1—Cl1 | 175.87 (16) | C10—C9—H9A | 121.0 |
N1—Pt1—Cl1 | 94.9 (2) | C8—C9—H9A | 121.0 |
Cl2—Pt1—Cl1 | 89.27 (8) | C11—C10—C9 | 120.8 (8) |
C2—N1—C14 | 118.9 (7) | C11—C10—H10A | 119.6 |
C2—N1—Pt1 | 127.2 (6) | C9—C10—H10A | 119.6 |
C14—N1—Pt1 | 113.8 (5) | N12—C11—C10 | 121.6 (8) |
N1—C2—C3 | 122.0 (9) | N12—C11—H11A | 119.2 |
N1—C2—H2A | 119.0 | C10—C11—H11A | 119.2 |
C3—C2—H2A | 119.0 | C11—N12—C13 | 118.7 (7) |
C4—C3—C2 | 119.2 (8) | C11—N12—Pt1 | 127.2 (5) |
C4—C3—H3A | 120.4 | C13—N12—Pt1 | 114.0 (5) |
C2—C3—H3A | 120.4 | N12—C13—C8 | 121.1 (7) |
C3—C4—C5 | 119.4 (8) | N12—C13—C14 | 115.0 (7) |
C3—C4—H4A | 120.3 | C8—C13—C14 | 123.9 (7) |
C5—C4—H4A | 120.3 | N1—C14—C5 | 121.6 (7) |
C4—C5—C14 | 118.9 (8) | N1—C14—C13 | 116.1 (6) |
C4—C5—C6 | 122.0 (8) | C5—C14—C13 | 122.3 (7) |
C14—C5—C6 | 119.1 (8) | N1A—C2A—C3A | 177.3 (14) |
O1—C6—C5 | 123.2 (10) | C2A—C3A—H3A1 | 109.5 |
O1—C6—C7 | 119.4 (11) | C2A—C3A—H3A2 | 109.5 |
C5—C6—C7 | 117.4 (7) | H3A1—C3A—H3A2 | 109.5 |
O2—C7—C8 | 121.7 (10) | C2A—C3A—H3A3 | 109.5 |
O2—C7—C6 | 118.4 (9) | H3A1—C3A—H3A3 | 109.5 |
C8—C7—C6 | 119.8 (9) | H3A2—C3A—H3A3 | 109.5 |
C9—C8—C13 | 119.6 (8) | ||
N12—Pt1—N1—C2 | −179.6 (6) | C10—C11—N12—C13 | −1.8 (11) |
Cl1—Pt1—N1—C2 | 0.9 (6) | C10—C11—N12—Pt1 | 177.0 (6) |
N12—Pt1—N1—C14 | −1.0 (5) | N1—Pt1—N12—C11 | −178.5 (6) |
Cl1—Pt1—N1—C14 | 179.4 (4) | Cl2—Pt1—N12—C11 | 1.6 (6) |
C14—N1—C2—C3 | 0.8 (10) | N1—Pt1—N12—C13 | 0.3 (5) |
Pt1—N1—C2—C3 | 179.3 (5) | Cl2—Pt1—N12—C13 | −179.6 (4) |
N1—C2—C3—C4 | −0.3 (11) | C11—N12—C13—C8 | 0.1 (10) |
C2—C3—C4—C5 | −0.3 (12) | Pt1—N12—C13—C8 | −178.9 (5) |
C3—C4—C5—C14 | 0.3 (12) | C11—N12—C13—C14 | 179.3 (6) |
C3—C4—C5—C6 | −177.9 (7) | Pt1—N12—C13—C14 | 0.4 (7) |
C4—C5—C6—O1 | 2.0 (13) | C9—C8—C13—N12 | 1.0 (11) |
C14—C5—C6—O1 | −176.2 (8) | C7—C8—C13—N12 | −178.6 (7) |
C4—C5—C6—C7 | −177.2 (7) | C9—C8—C13—C14 | −178.2 (7) |
C14—C5—C6—C7 | 4.6 (11) | C7—C8—C13—C14 | 2.2 (11) |
O1—C6—C7—O2 | 0.9 (14) | C2—N1—C14—C5 | −0.8 (10) |
C5—C6—C7—O2 | −179.9 (9) | Pt1—N1—C14—C5 | −179.4 (5) |
O1—C6—C7—C8 | 177.3 (8) | C2—N1—C14—C13 | −179.8 (6) |
C5—C6—C7—C8 | −3.5 (12) | Pt1—N1—C14—C13 | 1.5 (7) |
O2—C7—C8—C9 | −3.1 (14) | C4—C5—C14—N1 | 0.2 (11) |
C6—C7—C8—C9 | −179.4 (8) | C6—C5—C14—N1 | 178.5 (7) |
O2—C7—C8—C13 | 176.5 (9) | C4—C5—C14—C13 | 179.2 (7) |
C6—C7—C8—C13 | 0.1 (11) | C6—C5—C14—C13 | −2.6 (11) |
C13—C8—C9—C10 | −0.4 (12) | N12—C13—C14—N1 | −1.3 (9) |
C7—C8—C9—C10 | 179.2 (8) | C8—C13—C14—N1 | 178.0 (7) |
C8—C9—C10—C11 | −1.3 (13) | N12—C13—C14—C5 | 179.7 (6) |
C9—C10—C11—N12 | 2.4 (13) | C8—C13—C14—C5 | −1.1 (11) |
Experimental details
Crystal data | |
Chemical formula | [PtCl2(C12H6N2O2)]·C2H3N |
Mr | 517.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 6.7285 (2), 22.6380 (6), 9.7561 (3) |
β (°) | 98.0740 (17) |
V (Å3) | 1471.32 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 9.91 |
Crystal size (mm) | 0.40 × 0.06 × 0.05 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Gaussian (XPREP in SHELXL/PC; Sheldrick, 2008) |
Tmin, Tmax | 0.174, 0.629 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11801, 3345, 2837 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.094, 1.16 |
No. of reflections | 3345 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.48, −1.30 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL2013 (Sheldrick, 2008), XP SHELXTL/PC (Sheldrick, 2008), publCIF (Westrip, 2010).
Acknowledgements
This work was supported in part by The Robert A. Welch Foundation of Houston, Texas (grant No. AF-0005).
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