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The photophysical properties of transition metal complexes of the 5,6-dimethyl-2-(pyridin-2-yl)-1-(pyridin-2-ylmeth­yl)-1H-benzimidazole ligand are of inter­est. Di­chlorido­[5,6-dimethyl-2-(pyridin-2-yl)-1-(pyridin-2-ylmeth­yl)-1H-benzimidazole-κ2N2,N3]platinum(II), [PtCl2(C20H18N4)], is luminescent in the solid state at room temperature. The compound displays a distorted square-planar coordination geometry. The Pt—N(imidazole) bond length is shorter than the Pt—N(pyridine) bond length. The extended structure reveals that symmetry-related mol­ecules display weak C—H...N, C—H...Cl, and C—H...Pt hydrogen-bonding inter­actions that are clearly discernable in the Hirshfeld surface and fingerprint plots. The inter­molecular C—H...Pt and C—H...N inter­actions have been explored using density functional theory. The result of an analysis of the distance dependence of C—H...Pt yields a value consistent with that observed in the solid-state structure. The energy of inter­action for the C—H...Pt inter­action is found to be about −11 kJ mol−1.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617011573/uk3137sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011573/uk3137Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229617011573/uk3137Isup3.mol
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617011573/uk3137sup4.pdf
Two views of the NMR spectrum of (1) obtained in DMSO

CCDC reference: 1567122

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Dichlorido{5,6-dimethyl-2-(pyridin-2-yl)-1-(pyridin-2-ylmethyl)-1H-benzimidazole-κ2N2,N3}platinum(II) top
Crystal data top
[PtCl2(C20H18N4)]F(000) = 1112
Mr = 580.37Dx = 1.978 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.6134 (14) ÅCell parameters from 4378 reflections
b = 15.7166 (16) Åθ = 2.3–25.7°
c = 11.8754 (17) ŵ = 7.49 mm1
β = 100.376 (5)°T = 200 K
V = 1948.5 (4) Å3Parallelepiped, clear orange
Z = 40.30 × 0.30 × 0.10 mm
Data collection top
Bruker SMART X2S benchtop
diffractometer
4257 independent reflections
Radiation source: sealed microfocus tube3302 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromatorRint = 0.059
Detector resolution: 8.3330 pixels mm-1θmax = 27.1°, θmin = 2.3°
ω scansh = 137
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1819
Tmin = 0.38, Tmax = 0.52l = 1515
17697 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0239P)2]
where P = (Fo2 + 2Fc2)/3
4257 reflections(Δ/σ)max = 0.001
246 parametersΔρmax = 2.30 e Å3
0 restraintsΔρmin = 0.89 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pt10.68067 (2)0.59249 (2)0.61444 (2)0.02459 (8)
Cl10.77201 (12)0.52216 (9)0.77871 (13)0.0402 (4)
Cl20.88400 (13)0.62712 (11)0.58952 (15)0.0500 (4)
N10.4961 (4)0.5684 (2)0.6216 (4)0.0246 (10)
N20.2894 (4)0.5832 (2)0.5472 (4)0.0258 (10)
N30.5929 (4)0.6543 (2)0.4708 (4)0.0262 (10)
N40.2100 (5)0.7468 (3)0.5602 (4)0.0424 (13)
C10.4263 (4)0.5256 (3)0.6944 (5)0.0243 (11)
C20.2964 (5)0.5357 (3)0.6464 (5)0.0273 (12)
C30.2013 (5)0.5002 (3)0.6993 (5)0.0326 (13)
H30.11330.50880.66840.039*
C40.2376 (6)0.4525 (3)0.7971 (5)0.0373 (14)
C50.3714 (5)0.4417 (3)0.8451 (5)0.0341 (13)
C60.4666 (5)0.4793 (3)0.7922 (5)0.0323 (13)
H60.5550.47280.82310.039*
C70.4107 (4)0.6021 (3)0.5360 (4)0.0226 (11)
C80.4618 (5)0.6507 (3)0.4494 (5)0.0259 (12)
C90.3925 (5)0.6914 (3)0.3537 (5)0.0344 (14)
H90.30170.68710.33690.041*
C100.4565 (6)0.7375 (3)0.2843 (5)0.0411 (15)
H100.41010.76710.22010.049*
C110.5889 (6)0.7412 (3)0.3076 (5)0.0400 (15)
H110.63420.77310.260.048*
C120.6536 (5)0.6980 (3)0.4007 (5)0.0330 (13)
H120.74460.69920.41550.04*
C130.1693 (5)0.6084 (3)0.4725 (5)0.0316 (13)
H13A0.09720.57780.49670.038*
H13B0.17270.5910.3930.038*
C140.1443 (5)0.7031 (3)0.4747 (5)0.0294 (13)
C150.0569 (6)0.7390 (4)0.3881 (6)0.0488 (17)
H150.01170.70520.32780.059*
C160.0367 (7)0.8262 (4)0.3915 (7)0.065 (2)
H160.02140.85360.33240.078*
C170.1012 (7)0.8714 (4)0.4803 (7)0.060 (2)
H170.08730.93090.48580.072*
C180.1865 (7)0.8303 (4)0.5617 (6)0.059 (2)
H180.2320.8630.62320.071*
C410.1378 (6)0.4107 (4)0.8548 (6)0.0523 (18)
H41A0.05240.42980.81810.078*
H41B0.15280.42650.9360.078*
H41C0.14360.34880.84780.078*
C510.4093 (7)0.3882 (4)0.9496 (6)0.0550 (19)
H51A0.50270.38960.97320.083*
H51B0.38130.32950.93260.083*
H51C0.3690.41051.01150.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.02383 (11)0.02320 (13)0.02634 (13)0.00094 (8)0.00340 (8)0.00134 (10)
Cl10.0326 (7)0.0456 (9)0.0396 (9)0.0005 (6)0.0012 (6)0.0088 (7)
Cl20.0287 (7)0.0699 (11)0.0518 (11)0.0063 (7)0.0082 (7)0.0102 (9)
N10.024 (2)0.021 (2)0.026 (3)0.0047 (17)0.0011 (18)0.0039 (19)
N20.024 (2)0.021 (2)0.032 (3)0.0038 (17)0.0053 (18)0.002 (2)
N30.033 (2)0.019 (2)0.026 (3)0.0031 (18)0.0048 (19)0.001 (2)
N40.053 (3)0.025 (3)0.045 (4)0.007 (2)0.005 (3)0.008 (2)
C10.028 (3)0.018 (3)0.029 (3)0.001 (2)0.009 (2)0.003 (2)
C20.029 (3)0.022 (3)0.031 (3)0.001 (2)0.006 (2)0.006 (2)
C30.033 (3)0.028 (3)0.036 (4)0.002 (2)0.006 (2)0.006 (3)
C40.051 (4)0.026 (3)0.039 (4)0.010 (3)0.021 (3)0.007 (3)
C50.047 (4)0.026 (3)0.032 (4)0.002 (3)0.014 (3)0.004 (3)
C60.054 (4)0.020 (3)0.022 (3)0.000 (2)0.004 (3)0.002 (2)
C70.026 (3)0.020 (3)0.022 (3)0.002 (2)0.005 (2)0.006 (2)
C80.031 (3)0.023 (3)0.024 (3)0.006 (2)0.005 (2)0.003 (2)
C90.032 (3)0.037 (3)0.032 (4)0.003 (2)0.001 (2)0.005 (3)
C100.052 (4)0.038 (3)0.032 (4)0.008 (3)0.002 (3)0.009 (3)
C110.068 (4)0.026 (3)0.030 (4)0.004 (3)0.017 (3)0.008 (3)
C120.042 (3)0.029 (3)0.029 (3)0.005 (2)0.009 (3)0.001 (3)
C130.020 (3)0.031 (3)0.040 (4)0.005 (2)0.004 (2)0.002 (3)
C140.026 (3)0.032 (3)0.030 (3)0.006 (2)0.005 (2)0.001 (3)
C150.051 (4)0.050 (4)0.040 (4)0.013 (3)0.006 (3)0.002 (3)
C160.083 (5)0.058 (5)0.051 (5)0.039 (4)0.005 (4)0.026 (4)
C170.080 (5)0.042 (4)0.063 (6)0.023 (4)0.029 (4)0.005 (4)
C180.077 (5)0.037 (4)0.058 (5)0.011 (3)0.003 (4)0.014 (4)
C410.056 (4)0.051 (4)0.056 (5)0.013 (3)0.026 (4)0.001 (4)
C510.072 (5)0.052 (4)0.043 (5)0.014 (3)0.017 (4)0.011 (3)
Geometric parameters (Å, º) top
Pt1—N12.012 (4)C9—C101.368 (8)
Pt1—N32.037 (4)C9—H90.95
Pt1—Cl22.2959 (14)C10—C111.384 (8)
Pt1—Cl12.2992 (14)C10—H100.95
N1—C71.343 (6)C11—C121.372 (7)
N1—C11.406 (6)C11—H110.95
N2—C71.352 (6)C12—H120.95
N2—C21.385 (7)C13—C141.513 (6)
N2—C131.470 (6)C13—H13A0.99
N3—C121.332 (7)C13—H13B0.99
N3—C81.370 (6)C14—C151.375 (7)
N4—C141.317 (7)C15—C161.389 (8)
N4—C181.337 (7)C15—H150.95
C1—C61.372 (7)C16—C171.351 (9)
C1—C21.403 (6)C16—H160.95
C2—C31.398 (7)C17—C181.363 (9)
C3—C41.378 (8)C17—H170.95
C3—H30.95C18—H180.95
C4—C51.441 (8)C41—H41A0.98
C4—C411.512 (8)C41—H41B0.98
C5—C61.412 (7)C41—H41C0.98
C5—C511.493 (8)C51—H51A0.98
C6—H60.95C51—H51B0.98
C7—C81.461 (7)C51—H51C0.98
C8—C91.393 (7)
N1—Pt1—N379.81 (17)C9—C10—C11119.9 (5)
N1—Pt1—Cl2174.27 (13)C9—C10—H10120.1
N3—Pt1—Cl294.46 (12)C11—C10—H10120.1
N1—Pt1—Cl197.97 (13)C12—C11—C10119.0 (5)
N3—Pt1—Cl1177.73 (12)C12—C11—H11120.5
Cl2—Pt1—Cl187.76 (5)C10—C11—H11120.5
C7—N1—C1107.2 (4)N3—C12—C11122.0 (5)
C7—N1—Pt1115.0 (3)N3—C12—H12119.0
C1—N1—Pt1137.7 (3)C11—C12—H12119.0
C7—N2—C2107.2 (4)N2—C13—C14113.0 (4)
C7—N2—C13128.2 (5)N2—C13—H13A109.0
C2—N2—C13124.6 (4)C14—C13—H13A109.0
C12—N3—C8119.7 (5)N2—C13—H13B109.0
C12—N3—Pt1124.7 (4)C14—C13—H13B109.0
C8—N3—Pt1115.6 (3)H13A—C13—H13B107.8
C14—N4—C18116.6 (5)N4—C14—C15123.7 (5)
C6—C1—C2122.5 (5)N4—C14—C13117.1 (5)
C6—C1—N1131.0 (5)C15—C14—C13119.2 (5)
C2—C1—N1106.5 (4)C14—C15—C16118.0 (6)
N2—C2—C3131.6 (5)C14—C15—H15121.0
N2—C2—C1107.8 (4)C16—C15—H15121.0
C3—C2—C1120.6 (5)C17—C16—C15118.9 (6)
C4—C3—C2118.8 (5)C17—C16—H16120.6
C4—C3—H3120.6C15—C16—H16120.6
C2—C3—H3120.6C16—C17—C18118.9 (6)
C3—C4—C5120.2 (5)C16—C17—H17120.6
C3—C4—C41120.4 (6)C18—C17—H17120.6
C5—C4—C41119.4 (6)N4—C18—C17123.9 (6)
C6—C5—C4120.5 (5)N4—C18—H18118.1
C6—C5—C51119.9 (5)C17—C18—H18118.1
C4—C5—C51119.6 (5)C4—C41—H41A109.5
C1—C6—C5117.4 (5)C4—C41—H41B109.5
C1—C6—H6121.3H41A—C41—H41B109.5
C5—C6—H6121.3C4—C41—H41C109.5
N1—C7—N2111.3 (4)H41A—C41—H41C109.5
N1—C7—C8117.0 (4)H41B—C41—H41C109.5
N2—C7—C8131.7 (5)C5—C51—H51A109.5
N3—C8—C9120.1 (5)C5—C51—H51B109.5
N3—C8—C7112.6 (4)H51A—C51—H51B109.5
C9—C8—C7127.3 (5)C5—C51—H51C109.5
C10—C9—C8119.3 (5)H51A—C51—H51C109.5
C10—C9—H9120.4H51B—C51—H51C109.5
C8—C9—H9120.4
C7—N1—C1—C6178.4 (5)C2—N2—C7—C8179.5 (5)
Pt1—N1—C1—C62.8 (9)C13—N2—C7—C80.7 (8)
C7—N1—C1—C20.4 (5)C12—N3—C8—C91.0 (7)
Pt1—N1—C1—C2179.2 (4)Pt1—N3—C8—C9179.6 (4)
C7—N2—C2—C3179.4 (5)C12—N3—C8—C7178.6 (4)
C13—N2—C2—C30.6 (8)Pt1—N3—C8—C70.0 (5)
C7—N2—C2—C10.5 (5)N1—C7—C8—N30.2 (6)
C13—N2—C2—C1179.3 (4)N2—C7—C8—N3180.0 (5)
C6—C1—C2—N2178.2 (4)N1—C7—C8—C9179.8 (5)
N1—C1—C2—N20.1 (5)N2—C7—C8—C90.5 (9)
C6—C1—C2—C31.9 (8)N3—C8—C9—C102.6 (8)
N1—C1—C2—C3179.9 (4)C7—C8—C9—C10177.0 (5)
N2—C2—C3—C4177.6 (5)C8—C9—C10—C112.0 (9)
C1—C2—C3—C42.4 (8)C9—C10—C11—C120.1 (9)
C2—C3—C4—C51.7 (8)C8—N3—C12—C111.2 (8)
C2—C3—C4—C41178.1 (5)Pt1—N3—C12—C11177.3 (4)
C3—C4—C5—C60.5 (8)C10—C11—C12—N31.7 (8)
C41—C4—C5—C6179.3 (5)C7—N2—C13—C1467.0 (7)
C3—C4—C5—C51178.6 (5)C2—N2—C13—C14111.5 (5)
C41—C4—C5—C511.2 (8)C18—N4—C14—C151.2 (9)
C2—C1—C6—C50.6 (7)C18—N4—C14—C13179.6 (6)
N1—C1—C6—C5178.4 (5)N2—C13—C14—N416.9 (7)
C4—C5—C6—C10.1 (8)N2—C13—C14—C15162.4 (5)
C51—C5—C6—C1178.0 (5)N4—C14—C15—C160.2 (10)
C1—N1—C7—N20.7 (5)C13—C14—C15—C16179.3 (6)
Pt1—N1—C7—N2179.8 (3)C14—C15—C16—C171.4 (11)
C1—N1—C7—C8179.5 (4)C15—C16—C17—C181.8 (11)
Pt1—N1—C7—C80.4 (5)C14—N4—C18—C170.8 (11)
C2—N2—C7—N10.8 (5)C16—C17—C18—N40.8 (12)
C13—N2—C7—N1179.5 (4)
Hydrogen-bond geometry (Å, º) top
Cg refers to the centroid of the five-membered platinum diimine ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···Cl20.952.583.205 (6)124
C10—H10···N4i0.952.593.388 (8)142
C18—H18···Cl1ii0.952.763.546 (7)140
C11—H11···Pt1i0.952.833.722 (6)157
C11—H11···Cgi0.953.213.885 (6)130
C13—H13A···Cl2iii0.992.803.564 (6)135
C13—H13B···Cl1iv0.992.843.764 (6)155
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+1/2, z+3/2; (iii) x1, y, z; (iv) x+1, y+1, z+1.
 

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