metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Chlorido[6-phenyl-4-(p-tol­yl)-2,2′-bi­pyridyl-κ2N,N′]platinum(II)

aKey Laboratory of Special Display Technology and Academy of Opto-Electronic Technology, Hefei University of Technology, Ministry of Education, Hefei 230009, People's Republic of China, and bDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China
*Correspondence e-mail: bozhilu@mail.ustc.edu.cn

(Received 17 June 2008; accepted 3 July 2008; online 9 July 2008)

The asymmetric unit of the title compound, [Pt(C23H17N2)Cl], contains two independent mol­ecules with distinct dihedral angles between the central pyridyl and methylbenzene rings [7.77 (2) and 24.07 (2)°]. Short inter­molecular distances [3.582 (6) and 3.600 (6) Å] between the outer pyridine and the PtNC3 and PtN2C2 rings, respectively, indicate the existence of ππ inter­actions, which link the mol­ecules into stacks along the a axis. The crystal structure is further stabilized by weak C—H⋯π inter­actions.

Related literature

For related literature, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Catalano et al. (2000[Catalano, V. J., Benett, B. L., Yson, R. L. & Noll, B. C. (2000). J. Am. Chem. Soc. 122, 10056-10057.]); Kubicki et al. (2002[Kubicki, M., Borowiak, T., Dutkiewicz, G., Souhassou, M., Jelsch, C. & Lecomte, C. (2002). J. Phys. Chem. B, 106, 3706-3714.]).

[Scheme 1]

Experimental

Crystal data
  • [Pt(C23H17N2)Cl]

  • Mr = 551.92

  • Monoclinic, P 21

  • a = 7.379 (5) Å

  • b = 18.066 (5) Å

  • c = 14.222 (5) Å

  • β = 102.551 (5)°

  • V = 1850.6 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 7.74 mm−1

  • T = 298 (2) K

  • 0.50 × 0.30 × 0.20 mm

Data collection
  • Bruker APEX area-dectector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.113, Tmax = 0.307 (expected range = 0.078–0.213)

  • 14983 measured reflections

  • 8028 independent reflections

  • 6615 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.110

  • S = 0.72

  • 8028 reflections

  • 489 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 1.91 e Å−3

  • Δρmin = −0.65 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 3598 Friedel pairs

  • Flack parameter: 0.001 (11)

Table 1
Selected interatomic distances (Å)

Cg1, Cg2 and Cg3 are the centroids of the N4/C24–C28, Pt1/N1/C10/C11/C16 and Pt1/N1/N2/C5/C6 rings, respectively.

N3—Pt2 1.941 (8)
Pt2—C39 2.001 (11)
Pt2—N4 2.130 (9)
Pt2—Cl2 2.302 (3)
Pt1—N1 1.932 (7)
Pt1—C16 1.981 (9)
Pt1—N2 2.116 (8)
Pt1—Cl1 2.299 (3)
Cg1⋯Cg2i 3.582 (6)
Cg1⋯Cg3 3.600 (6)
Symmetry codes: (i) 1+x, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the Pt2/N3/C33/C34/C39 and C41–C45 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯Cg4ii 0.93 2.87 3.650 (14) 142
C14—H14⋯Cg5iii 0.93 2.71 3.445 (14) 136
Symmetry codes: (ii [-x+1, y+{\script{1\over 2}}, -z]; (iii) [-x, y-{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Recently, the bonding interaction between the closed-shell metal atoms or ions is gaining increasing attention, and while there exist numerous examples of fluorophenyl and cyanate platinum(II) centers aggregating with s2 ions such as Tl(I) or Pb(II) and d10 ions such as Au(I) or Ag(I)(Catalano et al., 2000), there are few reports of similar association in the case of alkyl platinum(II) complexes. As a part of our ongoing investigation on platinum complexes, the title compound (I) has been prepared and its crystal structure is presented here.

There are two crystallographically independent molecules in the asymmetric unit of (I) (Fig. 1). Each molecule contains a Pt atom coordinated in a distorted square-planar configuration with two Pt-N, one Pt-C and one Pt-Cl bonds (Table 1). Bond lengths and angles in the two molecules are similar and in a argreement with the values reported in the literature (Allen et al., 1987). The dihedral angles formed by the C17—C22 and C40—C45 benzene rings with N1/C6—C10 and N3/C29—C33 are 24.07 (2)°, 7.77 (2)°, respectively. The crystal packing of the structure exhibits π-π interactions proved by short intermolecular Cg1···Cg2 and Cg1···Cg3 distances of 3.582 (6) and 3.600 (6) Å, respectively; Cg1, Cg2 and Cg3 are centroids of N4/C24—C28, Pt1/N1/C10/C11/C16 and Pt1/N1/N2/C5/C6 rings, respectively (Table 1), which link the molecules into stacks along a axis. The crystal structure is further stabilized by the weak C—H···π interactions (Kubicki et al., 2002; Table 2).

Related literature top

For related literature, see: Allen et al. (1987); Catalano et al. (2000); Kubicki et al. (2002). Cg1, Cg2 and Cg3 are the centroids of the N4/C24—–C28, Pt1/N1/C10/C11/C16 and Pt1/N1/N2/C5/C6 rings, respectively.

Experimental top

For the preparation of 3,6-diimidazolyl-9-ethylcarbazole, A mixture of 4-(p-tolyl)-6-phenyl-2,2'-bipyridine (96.72 mg, 0.30 mmol) and K2PtCl4 (124.58 mg, 0.30 mmol) were heated at 363 K with CH3CN (10 ml) as solvent for 18 h. The mixture was cooled to room temperature. Then it was filtered and concentrated, the re-crystallization from DMF produced red single crystals (38.90 mg, Yield 83.88%).

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 - 0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). The highest residual peak [1.91 e Å-3] is situated 0.11 Å at atom H30.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : The content of asymmetric unit of the title compound showing the atomic numbering and 50% probability displacement ellipsoids.
Chlorido[6-phenyl-4-(p-tolyl)-2,2'-bipyridyl-κ2N,N']platinum(II) top
Crystal data top
[Pt(C23H17N2)Cl]Z = 4
Mr = 551.92F(000) = 1056
Monoclinic, P21Dx = 1.981 Mg m3
a = 7.379 (5) ÅMo Kα radiation, λ = 0.71069 Å
b = 18.066 (5) ŵ = 7.74 mm1
c = 14.222 (5) ÅT = 298 K
β = 102.551 (5)°Needle, red
V = 1850.6 (15) Å30.50 × 0.30 × 0.20 mm
Data collection top
Bruker APEX area-dectector
diffractometer
8028 independent reflections
Radiation source: fine-focus sealed tube6615 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 99
Tmin = 0.113, Tmax = 0.307k = 2323
14983 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.72(Δ/σ)max = 0.001
8028 reflectionsΔρmax = 1.91 e Å3
489 parametersΔρmin = 0.65 e Å3
1 restraintAbsolute structure: Flack (1983), 3598 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (11)
Crystal data top
[Pt(C23H17N2)Cl]V = 1850.6 (15) Å3
Mr = 551.92Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.379 (5) ŵ = 7.74 mm1
b = 18.066 (5) ÅT = 298 K
c = 14.222 (5) Å0.50 × 0.30 × 0.20 mm
β = 102.551 (5)°
Data collection top
Bruker APEX area-dectector
diffractometer
8028 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
6615 reflections with I > 2σ(I)
Tmin = 0.113, Tmax = 0.307Rint = 0.035
14983 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.110Δρmax = 1.91 e Å3
S = 0.72Δρmin = 0.65 e Å3
8028 reflectionsAbsolute structure: Flack (1983), 3598 Friedel pairs
489 parametersAbsolute structure parameter: 0.001 (11)
1 restraint
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C190.7020 (18)0.2281 (9)0.3338 (8)0.071 (3)
H190.73830.27340.36280.085*
N30.0093 (11)0.0772 (4)0.1479 (6)0.0455 (18)
Pt20.09764 (5)0.01160 (2)0.08126 (2)0.04713 (11)
Pt10.35781 (5)0.143731 (18)0.25831 (2)0.04136 (10)
Cl20.2212 (5)0.11757 (18)0.0028 (2)0.0741 (8)
Cl10.2643 (5)0.1428 (2)0.42342 (17)0.0687 (7)
N10.4326 (9)0.1481 (5)0.1195 (5)0.0391 (14)
C440.2848 (18)0.3505 (7)0.4362 (7)0.061 (3)
H440.27390.35800.49940.074*
C390.0498 (14)0.0514 (6)0.2157 (7)0.052 (2)
C80.5388 (12)0.1543 (6)0.0788 (6)0.044 (2)
C270.0172 (14)0.1830 (6)0.0774 (7)0.048 (2)
H270.03470.22870.05690.057*
C170.5989 (13)0.1582 (5)0.1879 (6)0.044 (2)
C400.2257 (12)0.2733 (5)0.2945 (6)0.0400 (19)
C330.0607 (13)0.0765 (5)0.2432 (7)0.044 (2)
C90.4583 (13)0.0905 (5)0.0326 (7)0.045 (2)
H90.44100.04930.06890.054*
C450.2185 (16)0.2857 (6)0.3890 (7)0.050 (2)
H450.16780.24960.42220.060*
C310.1507 (13)0.2049 (5)0.2432 (6)0.041 (2)
C410.3111 (14)0.3287 (6)0.2493 (6)0.047 (2)
H410.32260.32170.18610.056*
C120.2565 (16)0.0365 (6)0.0924 (9)0.058 (3)
H120.28380.04460.02620.069*
C100.4033 (12)0.0878 (5)0.0677 (7)0.0404 (19)
C420.3768 (16)0.3918 (6)0.2959 (8)0.056 (3)
H420.42990.42750.26330.067*
C430.3675 (18)0.4046 (6)0.3900 (8)0.061 (3)
N40.1077 (11)0.0607 (5)0.0380 (6)0.0500 (19)
C320.1347 (12)0.1397 (6)0.2932 (6)0.0457 (19)
H320.17360.13840.35990.055*
C290.0292 (12)0.1399 (7)0.0952 (5)0.0416 (18)
C250.1501 (16)0.0992 (8)0.2003 (8)0.064 (3)
H250.18930.08760.26530.077*
N20.4760 (11)0.2509 (5)0.2403 (5)0.0440 (17)
C160.2736 (12)0.0437 (5)0.2302 (7)0.0411 (19)
C210.637 (2)0.1009 (9)0.3453 (9)0.081 (4)
H210.62830.05920.38230.097*
C370.0303 (18)0.1362 (7)0.3487 (9)0.066 (3)
H370.04650.18390.36990.079*
C380.0821 (19)0.1205 (7)0.2512 (8)0.064 (3)
H380.13950.15700.20890.077*
C340.0295 (14)0.0036 (5)0.2848 (7)0.046 (2)
C300.0987 (12)0.2031 (5)0.1427 (6)0.0403 (19)
H300.11150.24550.10760.048*
C460.436 (2)0.4749 (8)0.4407 (10)0.088 (4)
H46A0.44400.51250.39410.131*
H46B0.55620.46690.48140.131*
H46C0.35100.49050.47930.131*
C110.3080 (12)0.0276 (6)0.1299 (7)0.044 (2)
C60.5122 (13)0.2106 (5)0.0761 (7)0.044 (2)
C180.6581 (17)0.2241 (7)0.2346 (8)0.059 (3)
H180.66820.26630.19850.070*
C280.0335 (13)0.1287 (5)0.0092 (6)0.045 (2)
C220.594 (2)0.0974 (8)0.2454 (8)0.074 (4)
H220.56080.05190.21610.089*
C70.5620 (15)0.2149 (6)0.0231 (7)0.047 (2)
H70.61120.25870.05260.057*
C240.1648 (14)0.0476 (7)0.1329 (7)0.056 (3)
H240.21610.00180.15300.068*
C130.1620 (16)0.0893 (6)0.1555 (9)0.062 (3)
H130.12590.13370.13200.074*
C40.6150 (16)0.3362 (6)0.1195 (8)0.057 (2)
H40.65260.34870.05480.068*
C350.0742 (16)0.0126 (7)0.3828 (8)0.060 (2)
H350.12430.02380.42710.072*
C50.5346 (14)0.2690 (5)0.1462 (7)0.045 (2)
C140.1223 (16)0.0757 (7)0.2530 (10)0.062 (3)
H140.05780.11110.29480.075*
C150.1765 (14)0.0102 (8)0.2903 (8)0.056 (2)
H150.14720.00240.35660.067*
C20.5799 (19)0.3664 (7)0.2857 (9)0.068 (3)
H20.59290.39920.33420.082*
C10.5009 (15)0.2984 (7)0.3080 (8)0.057 (3)
H10.46330.28500.37240.069*
C260.0770 (16)0.1693 (7)0.1738 (7)0.063 (3)
H260.06940.20520.21970.075*
C30.6396 (17)0.3855 (7)0.1910 (9)0.065 (3)
H30.69620.43110.17440.078*
C200.6946 (17)0.1699 (9)0.3895 (7)0.071 (4)
C360.044 (2)0.0835 (7)0.4141 (9)0.069 (3)
H360.07380.09480.47940.082*
C230.744 (2)0.1739 (10)0.5006 (9)0.086 (4)
H23A0.84540.14080.52490.129*
H23B0.63830.15970.52540.129*
H23C0.77980.22350.52050.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C190.077 (8)0.085 (9)0.050 (6)0.004 (7)0.013 (6)0.018 (6)
N30.051 (4)0.042 (4)0.038 (4)0.008 (4)0.003 (3)0.003 (3)
Pt20.0528 (2)0.04704 (19)0.04067 (19)0.00263 (18)0.00828 (15)0.00699 (16)
Pt10.04689 (18)0.03779 (16)0.03740 (17)0.00176 (16)0.00475 (13)0.00092 (15)
Cl20.102 (2)0.0613 (17)0.0567 (16)0.0187 (17)0.0123 (16)0.0182 (14)
Cl10.0953 (19)0.0648 (14)0.0393 (11)0.0045 (19)0.0002 (12)0.0015 (14)
N10.045 (3)0.035 (3)0.037 (3)0.009 (4)0.008 (3)0.003 (4)
C440.084 (8)0.059 (7)0.037 (5)0.006 (6)0.005 (5)0.004 (5)
C390.056 (6)0.055 (6)0.048 (5)0.000 (5)0.016 (5)0.009 (5)
C80.039 (4)0.055 (6)0.038 (4)0.015 (4)0.010 (3)0.000 (4)
C270.055 (6)0.047 (5)0.039 (5)0.012 (5)0.009 (4)0.003 (4)
C170.048 (5)0.049 (6)0.035 (4)0.008 (4)0.008 (3)0.005 (4)
C400.048 (5)0.033 (4)0.039 (4)0.007 (4)0.010 (4)0.005 (4)
C330.044 (5)0.041 (5)0.043 (5)0.005 (4)0.005 (4)0.002 (4)
C90.046 (5)0.040 (5)0.049 (5)0.001 (4)0.012 (4)0.004 (4)
C450.073 (6)0.040 (5)0.035 (5)0.010 (5)0.007 (4)0.003 (4)
C310.049 (5)0.038 (5)0.036 (4)0.006 (4)0.010 (4)0.001 (4)
C410.067 (6)0.044 (5)0.031 (4)0.007 (5)0.014 (4)0.003 (4)
C120.068 (7)0.049 (6)0.056 (6)0.001 (5)0.012 (5)0.010 (5)
C100.041 (5)0.037 (4)0.042 (5)0.008 (4)0.006 (4)0.003 (4)
C420.067 (6)0.045 (5)0.053 (6)0.005 (5)0.005 (5)0.001 (5)
C430.080 (8)0.047 (5)0.044 (6)0.003 (6)0.011 (5)0.003 (5)
N40.044 (4)0.058 (5)0.041 (4)0.001 (4)0.005 (3)0.006 (4)
C320.052 (5)0.055 (5)0.030 (4)0.008 (5)0.008 (3)0.003 (5)
C290.048 (4)0.051 (5)0.027 (3)0.010 (5)0.009 (3)0.005 (4)
C250.067 (7)0.091 (9)0.035 (5)0.014 (7)0.012 (5)0.010 (6)
N20.049 (4)0.046 (4)0.035 (4)0.005 (4)0.003 (3)0.005 (3)
C160.040 (4)0.035 (4)0.045 (5)0.004 (4)0.003 (4)0.000 (4)
C210.119 (12)0.073 (9)0.048 (7)0.011 (8)0.015 (7)0.010 (6)
C370.082 (8)0.055 (6)0.060 (7)0.013 (6)0.015 (6)0.007 (5)
C380.077 (7)0.053 (6)0.056 (7)0.010 (6)0.002 (6)0.006 (5)
C340.056 (5)0.035 (5)0.047 (5)0.010 (4)0.015 (4)0.000 (4)
C300.042 (5)0.041 (5)0.037 (4)0.005 (4)0.007 (4)0.001 (4)
C460.127 (12)0.060 (8)0.070 (8)0.016 (8)0.010 (8)0.007 (6)
C110.033 (4)0.044 (5)0.052 (5)0.002 (4)0.005 (4)0.001 (4)
C60.041 (5)0.043 (5)0.045 (5)0.000 (4)0.006 (4)0.000 (4)
C180.067 (7)0.060 (6)0.050 (6)0.005 (6)0.015 (5)0.007 (5)
C280.054 (5)0.051 (6)0.031 (4)0.020 (4)0.011 (4)0.002 (4)
C220.108 (10)0.066 (8)0.044 (6)0.007 (8)0.007 (6)0.003 (5)
C70.060 (6)0.041 (5)0.041 (5)0.001 (4)0.010 (4)0.006 (4)
C240.050 (5)0.072 (7)0.042 (5)0.002 (5)0.000 (4)0.016 (5)
C130.063 (7)0.041 (5)0.078 (8)0.009 (5)0.005 (6)0.002 (5)
C40.076 (7)0.041 (5)0.053 (6)0.000 (5)0.014 (5)0.001 (5)
C350.077 (7)0.045 (5)0.054 (5)0.001 (6)0.006 (5)0.005 (5)
C50.052 (5)0.042 (5)0.040 (5)0.002 (4)0.008 (4)0.004 (4)
C140.058 (6)0.047 (6)0.082 (9)0.008 (5)0.013 (6)0.016 (6)
C150.053 (5)0.056 (6)0.053 (5)0.010 (6)0.000 (4)0.006 (6)
C20.084 (8)0.060 (7)0.064 (7)0.003 (7)0.025 (6)0.018 (6)
C10.061 (6)0.055 (6)0.054 (6)0.005 (5)0.011 (5)0.019 (5)
C260.066 (7)0.081 (8)0.039 (5)0.017 (6)0.006 (5)0.003 (5)
C30.069 (7)0.048 (6)0.076 (8)0.017 (6)0.011 (6)0.005 (6)
C200.069 (7)0.111 (11)0.030 (5)0.006 (7)0.007 (5)0.006 (6)
C360.093 (8)0.063 (7)0.055 (7)0.001 (7)0.026 (6)0.017 (6)
C230.105 (10)0.105 (11)0.048 (7)0.000 (9)0.016 (7)0.010 (7)
Geometric parameters (Å, º) top
C19—C201.32 (2)C32—H320.9300
C19—C181.379 (16)C29—C301.369 (14)
C19—H190.9300C29—C281.470 (11)
N3—C331.325 (12)C25—C241.358 (18)
N3—C291.384 (14)C25—C261.397 (18)
N3—Pt21.941 (8)C25—H250.9300
Pt2—C392.001 (11)N2—C11.333 (13)
Pt2—N42.130 (9)N2—C51.354 (12)
Pt2—Cl22.302 (3)C16—C151.388 (14)
Pt1—N11.932 (7)C16—C111.422 (14)
Pt1—C161.981 (9)C21—C221.388 (17)
Pt1—N22.116 (8)C21—C201.42 (2)
Pt1—Cl12.299 (3)C21—H210.9300
N1—C61.357 (13)C37—C361.360 (18)
N1—C101.358 (13)C37—C381.384 (16)
C44—C451.385 (15)C37—H370.9300
C44—C431.390 (17)C38—H380.9300
C44—H440.9300C34—C351.391 (14)
C39—C381.387 (17)C30—H300.9300
C39—C341.432 (14)C46—H46A0.9600
C8—C71.384 (14)C46—H46B0.9600
C8—C91.394 (14)C46—H46C0.9600
C8—C171.520 (12)C6—C71.381 (13)
C27—C261.368 (14)C6—C51.486 (14)
C27—C281.403 (14)C18—H180.9300
C27—H270.9300C22—H220.9300
C17—C221.374 (16)C7—H70.9300
C17—C181.388 (16)C24—H240.9300
C40—C451.375 (13)C13—C141.375 (17)
C40—C411.410 (13)C13—H130.9300
C40—C311.480 (13)C4—C51.368 (14)
C33—C321.393 (15)C4—C31.393 (16)
C33—C341.482 (13)C4—H40.9300
C9—C101.396 (13)C35—C361.390 (17)
C9—H90.9300C35—H350.9300
C45—H450.9300C14—C151.391 (18)
C31—C321.395 (14)C14—H140.9300
C31—C301.397 (13)C15—H150.9300
C41—C421.354 (15)C2—C31.367 (19)
C41—H410.9300C2—C11.367 (18)
C12—C111.364 (15)C2—H20.9300
C12—C131.390 (16)C1—H10.9300
C12—H120.9300C26—H260.9300
C10—C111.480 (14)C3—H30.9300
C42—C431.374 (16)C20—C231.544 (15)
C42—H420.9300C36—H360.9300
C43—C461.493 (17)C23—H23A0.9600
N4—C241.344 (13)C23—H23B0.9600
N4—C281.370 (13)C23—H23C0.9600
Cg1···Cg2i3.582 (6)Cg1···Cg33.600 (6)
C20—C19—C18122.7 (13)C22—C21—C20118.3 (12)
C20—C19—H19118.7C22—C21—H21120.9
C18—C19—H19118.7C20—C21—H21120.9
C33—N3—C29121.4 (8)C36—C37—C38121.6 (11)
C33—N3—Pt2119.2 (7)C36—C37—H37119.2
C29—N3—Pt2119.4 (6)C38—C37—H37119.2
N3—Pt2—C3982.1 (4)C37—C38—C39121.1 (11)
N3—Pt2—N479.8 (3)C37—C38—H38119.4
C39—Pt2—N4161.8 (4)C39—C38—H38119.4
N3—Pt2—Cl2179.3 (2)C35—C34—C39121.0 (9)
C39—Pt2—Cl297.7 (3)C35—C34—C33124.3 (9)
N4—Pt2—Cl2100.5 (2)C39—C34—C33114.7 (9)
N1—Pt1—C1682.2 (4)C29—C30—C31121.0 (9)
N1—Pt1—N279.6 (3)C29—C30—H30119.5
C16—Pt1—N2161.8 (3)C31—C30—H30119.5
N1—Pt1—Cl1177.9 (3)C43—C46—H46A109.5
C16—Pt1—Cl199.3 (3)C43—C46—H46B109.5
N2—Pt1—Cl198.9 (2)H46A—C46—H46B109.5
C6—N1—C10121.6 (7)C43—C46—H46C109.5
C6—N1—Pt1119.9 (6)H46A—C46—H46C109.5
C10—N1—Pt1118.5 (6)H46B—C46—H46C109.5
C45—C44—C43120.7 (10)C12—C11—C16124.1 (9)
C45—C44—H44119.7C12—C11—C10121.8 (9)
C43—C44—H44119.7C16—C11—C10114.1 (8)
C38—C39—C34116.9 (10)N1—C6—C7120.4 (9)
C38—C39—Pt2131.6 (8)N1—C6—C5112.7 (8)
C34—C39—Pt2111.6 (8)C7—C6—C5126.9 (9)
C7—C8—C9118.6 (8)C19—C18—C17120.9 (12)
C7—C8—C17120.2 (9)C19—C18—H18119.6
C9—C8—C17121.3 (9)C17—C18—H18119.6
C26—C27—C28120.6 (11)N4—C28—C27120.5 (8)
C26—C27—H27119.7N4—C28—C29116.3 (9)
C28—C27—H27119.7C27—C28—C29123.2 (10)
C22—C17—C18116.6 (9)C17—C22—C21122.8 (12)
C22—C17—C8122.1 (9)C17—C22—H22118.6
C18—C17—C8121.3 (9)C21—C22—H22118.6
C45—C40—C41116.5 (9)C6—C7—C8120.0 (9)
C45—C40—C31121.9 (9)C6—C7—H7120.0
C41—C40—C31121.6 (8)C8—C7—H7120.0
N3—C33—C32120.5 (9)N4—C24—C25122.1 (11)
N3—C33—C34112.5 (8)N4—C24—H24118.9
C32—C33—C34127.0 (9)C25—C24—H24118.9
C8—C9—C10120.6 (9)C14—C13—C12119.7 (11)
C8—C9—H9119.7C14—C13—H13120.1
C10—C9—H9119.7C12—C13—H13120.1
C40—C45—C44121.7 (10)C5—C4—C3118.9 (10)
C40—C45—H45119.1C5—C4—H4120.6
C44—C45—H45119.1C3—C4—H4120.6
C32—C31—C30117.8 (8)C36—C35—C34119.7 (11)
C32—C31—C40121.2 (8)C36—C35—H35120.2
C30—C31—C40120.9 (8)C34—C35—H35120.2
C42—C41—C40121.4 (9)N2—C5—C4120.9 (9)
C42—C41—H41119.3N2—C5—C6115.7 (8)
C40—C41—H41119.3C4—C5—C6123.3 (9)
C11—C12—C13118.3 (11)C13—C14—C15121.4 (10)
C11—C12—H12120.9C13—C14—H14119.3
C13—C12—H12120.9C15—C14—H14119.3
N1—C10—C9118.8 (8)C16—C15—C14120.9 (10)
N1—C10—C11112.1 (8)C16—C15—H15119.5
C9—C10—C11129.1 (9)C14—C15—H15119.5
C41—C42—C43122.0 (11)C3—C2—C1119.1 (11)
C41—C42—H42119.0C3—C2—H2120.5
C43—C42—H42119.0C1—C2—H2120.5
C42—C43—C44117.5 (10)N2—C1—C2122.0 (11)
C42—C43—C46122.1 (12)N2—C1—H1119.0
C44—C43—C46120.4 (11)C2—C1—H1119.0
C24—N4—C28118.4 (9)C27—C26—C25117.1 (11)
C24—N4—Pt2129.8 (8)C27—C26—H26121.4
C28—N4—Pt2111.6 (6)C25—C26—H26121.4
C33—C32—C31120.0 (8)C2—C3—C4119.5 (11)
C33—C32—H32120.0C2—C3—H3120.3
C31—C32—H32120.0C4—C3—H3120.3
C30—C29—N3119.2 (7)C19—C20—C21118.7 (10)
C30—C29—C28128.0 (10)C19—C20—C23122.9 (13)
N3—C29—C28112.8 (9)C21—C20—C23118.4 (12)
C24—C25—C26121.1 (10)C37—C36—C35119.6 (11)
C24—C25—H25119.4C37—C36—H36120.2
C26—C25—H25119.4C35—C36—H36120.2
C1—N2—C5119.6 (9)C20—C23—H23A109.5
C1—N2—Pt1128.3 (7)C20—C23—H23B109.5
C5—N2—Pt1112.1 (6)H23A—C23—H23B109.5
C15—C16—C11115.5 (9)C20—C23—H23C109.5
C15—C16—Pt1131.2 (8)H23A—C23—H23C109.5
C11—C16—Pt1113.1 (7)H23B—C23—H23C109.5
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg4ii0.932.873.650 (14)142
C14—H14···Cg5iii0.932.713.445 (14)136
Symmetry codes: (ii) x+1, y+1/2, z; (iii) x, y1/2, z.

Experimental details

Crystal data
Chemical formula[Pt(C23H17N2)Cl]
Mr551.92
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)7.379 (5), 18.066 (5), 14.222 (5)
β (°) 102.551 (5)
V3)1850.6 (15)
Z4
Radiation typeMo Kα
µ (mm1)7.74
Crystal size (mm)0.50 × 0.30 × 0.20
Data collection
DiffractometerBruker APEX area-dectector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.113, 0.307
No. of measured, independent and
observed [I > 2σ(I)] reflections
14983, 8028, 6615
Rint0.035
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.110, 0.72
No. of reflections8028
No. of parameters489
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.91, 0.65
Absolute structureFlack (1983), 3598 Friedel pairs
Absolute structure parameter0.001 (11)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected interatomic distances (Å) top
N3—Pt21.941 (8)Pt1—N11.932 (7)
Pt2—C392.001 (11)Pt1—C161.981 (9)
Pt2—N42.130 (9)Pt1—N22.116 (8)
Pt2—Cl22.302 (3)Pt1—Cl12.299 (3)
Cg1···Cg2i3.582 (6)Cg1···Cg33.600 (6)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg4ii0.932.873.650 (14)142
C14—H14···Cg5iii0.932.713.445 (14)136
Symmetry codes: (ii) x+1, y+1/2, z; (iii) x, y1/2, z.
 

Acknowledgements

We thank Professor W.-T. Yu of Shan Dong University for his kind assistance with the X-ray structure determination.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCatalano, V. J., Benett, B. L., Yson, R. L. & Noll, B. C. (2000). J. Am. Chem. Soc. 122, 10056–10057.  Web of Science CSD CrossRef CAS Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationKubicki, M., Borowiak, T., Dutkiewicz, G., Souhassou, M., Jelsch, C. & Lecomte, C. (2002). J. Phys. Chem. B, 106, 3706–3714.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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