Chloro­methyl(η⁴-norborna­diene)­platinum(II), an unsymmetrical substituted precursor for Pt^II complexes

The title compound, [PtCl(CH₃)(C₇H₈)] or [(nbd)PtClMe] (nbd is norborna­diene), was formed in a partial substitution reaction of di­chloro(η⁴-norborna­diene)­platinum(II). The Pt atom exhibits tetrahedral coordination, involving the two η²–π bonds to the norborna­diene, one chlorine and one methyl substituent. Probably as a result of the symmetry of the norborna­diene and the approximately equal size of the methyl and chlorine substituents, these two substituents are disordered and have been refined, each with half-occupancy.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• H-atom completeness 73%
• R factor = 0.027
• wR factor = 0.073
• Data-to-parameter ratio = 22.4

checkCIF results

No syntax errors found

Structure: I
------------

ADDSYM reports no extra symmetry

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C8 H11 Cl1 Pt1
          Atom count from the _atom_site data:  C8 H8 Cl1 Pt1

ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.649
          Tmax scaled      0.182 Tmin scaled      0.027

CELLZ_01
         From the CIF: _cell_formula_units_Z    8
         From the CIF: _chemical_formula_sum  C8 H11 Cl Pt
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         64.00     64.00    0.00
         H         88.00     64.00   24.00
         Cl         8.00      8.00    0.00
         Pt         8.00      8.00    0.00
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[PtCl(CH3)(C7H8)]	F(000) = 1208
Mr = 337.72	Dx = 2.662 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0526 (7) Å	Cell parameters from 4347 reflections
b = 11.8020 (6) Å	θ = 2.5–28.3°
c = 12.6014 (6) Å	µ = 17.04 mm^−1
β = 120.636 (1)°	T = 213 K
V = 1670.25 (15) Å^3	Prism, colorless
Z = 8	0.52 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2062 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.041, Tmax = 0.281	k = −15→13
5677 measured reflections	l = −16→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 3.7959P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2062 reflections	Δρmax = 1.72 e Å^−3
92 parameters	Δρmin = −1.65 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00090 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt	0.150494 (14)	0.887511 (14)	0.041500 (14)	0.02515 (11)
Cl1	0.1274 (3)	0.7905 (2)	0.1812 (2)	0.0537 (6)	0.50
C1A	0.1274 (3)	0.7905 (2)	0.1812 (2)	0.0537 (6)	0.50
C1	0.2707 (6)	1.0922 (5)	0.0605 (6)	0.0409 (12)
H1	0.2576	1.1720	0.0749	0.049*
C2	0.2927 (6)	1.0055 (5)	0.1608 (6)	0.0460 (13)
H2A	0.3095	1.0274	0.2440	0.055*
Cl2	−0.03286 (18)	0.8183 (2)	−0.10247 (19)	0.0402 (5)	0.50
C2A	−0.03286 (18)	0.8183 (2)	−0.10247 (19)	0.0402 (5)	0.50
C3	0.3441 (5)	0.9121 (5)	0.1394 (6)	0.0416 (12)
H3A	0.4004	0.8611	0.2062	0.050*
C4	0.3547 (5)	0.9400 (5)	0.0277 (6)	0.0393 (11)
H4	0.4104	0.8936	0.0144	0.047*
C5	0.2230 (5)	0.9405 (5)	−0.0756 (5)	0.0397 (12)
H5A	0.1951	0.9082	−0.1584	0.048*
C6	0.1715 (5)	1.0337 (5)	−0.0565 (5)	0.0412 (12)
H6A	0.1034	1.0750	−0.1239	0.049*
C7	0.3789 (5)	1.0667 (5)	0.0468 (6)	0.0446 (13)
H7A	0.3743	1.1042	−0.0249	0.054*
H7B	0.4548	1.0844	0.1215	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt	0.02494 (14)	0.02399 (14)	0.02449 (13)	−0.00040 (5)	0.01112 (9)	0.00033 (5)
Cl1	0.0684 (16)	0.0515 (14)	0.0388 (11)	0.0018 (12)	0.0257 (11)	0.0060 (10)
C1A	0.0684 (16)	0.0515 (14)	0.0388 (11)	0.0018 (12)	0.0257 (11)	0.0060 (10)
C1	0.052 (3)	0.027 (2)	0.051 (3)	−0.007 (2)	0.032 (3)	−0.003 (2)
C2	0.062 (4)	0.037 (3)	0.044 (3)	−0.012 (3)	0.031 (3)	−0.009 (2)
Cl2	0.0282 (9)	0.0503 (12)	0.0314 (9)	0.0031 (8)	0.0074 (7)	0.0001 (8)
C2A	0.0282 (9)	0.0503 (12)	0.0314 (9)	0.0031 (8)	0.0074 (7)	0.0001 (8)
C3	0.035 (3)	0.039 (3)	0.042 (3)	−0.002 (2)	0.013 (2)	0.006 (2)
C4	0.033 (2)	0.037 (3)	0.052 (3)	0.000 (2)	0.025 (2)	−0.005 (2)
C5	0.044 (3)	0.044 (3)	0.037 (3)	−0.008 (2)	0.025 (2)	−0.008 (2)
C6	0.035 (3)	0.041 (3)	0.042 (3)	0.003 (2)	0.015 (2)	0.014 (2)
C7	0.043 (3)	0.033 (3)	0.060 (4)	−0.008 (2)	0.028 (3)	0.004 (3)

Geometric parameters (Å, º)

Pt—C2	2.191 (6)	C1—C7	1.537 (9)
Pt—C3	2.195 (6)	C1—C6	1.543 (8)
Pt—C5	2.210 (5)	C2—C3	1.387 (9)
Pt—C6	2.218 (5)	C3—C4	1.518 (9)
Pt—Cl1	2.245 (2)	C4—C7	1.522 (8)
Pt—C2A	2.294 (2)	C4—C5	1.539 (8)
C1—C2	1.535 (9)	C5—C6	1.373 (8)
C2—Pt—C3	36.9 (2)	C7—C1—C6	100.2 (5)
C2—Pt—C5	77.1 (2)	C3—C2—C1	106.0 (5)
C3—Pt—C5	64.9 (2)	C3—C2—Pt	71.7 (3)
C2—Pt—C6	65.5 (2)	C1—C2—Pt	97.0 (4)
C3—Pt—C6	77.1 (2)	C2—C3—C4	106.8 (5)
C5—Pt—C6	36.1 (2)	C2—C3—Pt	71.4 (4)
C2—Pt—Cl1	101.04 (17)	C4—C3—Pt	97.5 (3)
C3—Pt—Cl1	101.71 (18)	C3—C4—C7	100.1 (5)
C5—Pt—Cl1	160.35 (18)	C3—C4—C5	101.2 (4)
C6—Pt—Cl1	159.54 (18)	C7—C4—C5	100.5 (5)
C2—Pt—C2A	161.21 (19)	C6—C5—C4	106.9 (5)
C3—Pt—C2A	158.48 (19)	C6—C5—Pt	72.2 (3)
C5—Pt—C2A	101.64 (15)	C4—C5—Pt	96.2 (3)
C6—Pt—C2A	102.23 (16)	C5—C6—C1	106.2 (5)
Cl1—Pt—C2A	86.31 (9)	C5—C6—Pt	71.6 (3)
C2—C1—C7	99.5 (5)	C1—C6—Pt	95.6 (3)
C2—C1—C6	101.6 (4)	C4—C7—C1	94.7 (4)
C7—C1—C2—C3	−33.9 (6)	C3—C4—C5—Pt	−3.8 (4)
C6—C1—C2—C3	68.6 (6)	C7—C4—C5—Pt	−106.5 (4)
C7—C1—C2—Pt	−106.9 (4)	C2—Pt—C5—C6	−66.0 (3)
C6—C1—C2—Pt	−4.3 (5)	C3—Pt—C5—C6	−102.9 (4)
C5—Pt—C2—C3	−65.1 (4)	Cl1—Pt—C5—C6	−152.7 (4)
C6—Pt—C2—C3	−101.4 (4)	Cl2—Pt—C5—C6	94.8 (3)
Cl1—Pt—C2—C3	94.9 (3)	C2—Pt—C5—C4	39.8 (4)
Cl2—Pt—C2—C3	−153.5 (4)	C3—Pt—C5—C4	2.9 (3)
C3—Pt—C2—C1	104.6 (5)	C6—Pt—C5—C4	105.8 (5)
C5—Pt—C2—C1	39.5 (4)	Cl1—Pt—C5—C4	−47.0 (7)
C6—Pt—C2—C1	3.2 (4)	Cl2—Pt—C5—C4	−159.4 (3)
Cl1—Pt—C2—C1	−160.5 (3)	C4—C5—C6—C1	−0.6 (6)
Cl2—Pt—C2—C1	−48.8 (7)	Pt—C5—C6—C1	90.6 (4)
C1—C2—C3—C4	0.2 (6)	C4—C5—C6—Pt	−91.2 (4)
Pt—C2—C3—C4	92.4 (4)	C2—C1—C6—C5	−68.2 (6)
C1—C2—C3—Pt	−92.2 (4)	C7—C1—C6—C5	33.8 (6)
C5—Pt—C3—C2	102.4 (4)	C2—C1—C6—Pt	4.3 (5)
C6—Pt—C3—C2	66.3 (4)	C7—C1—C6—Pt	106.3 (4)
Cl1—Pt—C3—C2	−92.8 (3)	C2—Pt—C6—C5	102.0 (4)
Cl2—Pt—C3—C2	156.9 (4)	C3—Pt—C6—C5	64.9 (4)
C2—Pt—C3—C4	−105.3 (5)	Cl1—Pt—C6—C5	153.8 (4)
C5—Pt—C3—C4	−2.9 (3)	Cl2—Pt—C6—C5	−93.1 (3)
C6—Pt—C3—C4	−39.0 (4)	C2—Pt—C6—C1	−3.2 (4)
Cl1—Pt—C3—C4	161.9 (3)	C3—Pt—C6—C1	−40.3 (4)
Cl2—Pt—C3—C4	51.6 (7)	C5—Pt—C6—C1	−105.2 (5)
C2—C3—C4—C7	34.0 (6)	Cl1—Pt—C6—C1	48.6 (6)
Pt—C3—C4—C7	106.8 (4)	Cl2—Pt—C6—C1	161.7 (3)
C2—C3—C4—C5	−68.9 (6)	C3—C4—C7—C1	−52.4 (5)
Pt—C3—C4—C5	3.8 (4)	C5—C4—C7—C1	51.2 (5)
C3—C4—C5—C6	69.5 (6)	C2—C1—C7—C4	52.2 (5)
C7—C4—C5—C6	−33.2 (6)	C6—C1—C7—C4	−51.5 (5)