trans-Bis­(carbazol-3-yl­ethynyl)­bis­(tri-n-butyl­phosphine)­platinum(II)

Khan, M.S.; Al-Saadi, R.K.M.; Male, L.; Raithby, P.R.; Bjernemose, J.K.

doi:10.1107/S1600536803017872

trans-Bis(carbazol-3-ylethynyl)bis(tri-n-butylphosphine)platinum(II)

M. S. Khan, R. K. M. Al-Saadi, L. Male, P. R. Raithby and J. K. Bjernemose

The title compound, [Pt(C₁₂H₂₇P)₂(C₁₄H₈N)₂], is a mononuclear Pt^II di-yne exhibiting π-conjugation along the molecular backbone. It is used as a model species for rigid-rod platinum poly yne compounds of which it is a precursor. Such compounds are of interest due to the extended π-conjugation through the hetero-aromatic linker unit in the backbone.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017872/ww6109sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017872/ww6109Isup2.hkl Contains datablock I

CCDC reference: 222816

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.024
wR factor = 0.062
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.538     0.683
            Tmin and Tmax expected:      0.414     0.674
            RR =      1.284
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.27
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pt1    -   C14      =       7.64 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C13      =       1.45 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            C11 -C10 -C13 -C14  -153.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            C9  -C10 -C13 -C14    26.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            C10 -C13 -C14 -PT1    31.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         51
            C13 -C14 -PT1 -C14    92.00 72.00   1.555   1.555   1.555   3.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         52
            C13 -C14 -PT1 -P1   -170.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         53
            C13 -C14 -PT1 -P1     10.00  7.00   1.555   1.555   1.555   3.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         60
            C23 -P1  -PT1 -P1     85.00 31.00   1.555   1.555   1.555   3.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         61
            C15 -P1  -PT1 -P1   -154.00 31.00   1.555   1.555   1.555   3.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         62
            C19 -P1  -PT1 -P1    -36.00 31.00   1.555   1.555   1.555   3.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  18 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In this paper, we report the structural characterization of the title compound, (I), which is a mononuclear platinum(II) di-yne species, trans-[Pt(PⁿBu₃)₂(—C≡CR)₂] (R = carbazol-3-yl). Such platinum-containing species form the building blocks for rigid-rod organometallic poly-ynes of general formula trans-[Pt(PⁿBu₃)₂—C≡C—R—C≡C—]_∞ (R = aromatic or heteroaromatic linker unit). Platinum(II) poly-ynes are of immense current interest due to π-electron conjugation along the backbone, donor–acceptor metal–ligand interactions and novel photophysical properties (Wittmann et al., 1994; Beljonne et al., 1996; Younus et al., 1998; Chawdhury et al., 1998, 1999; Khan et al., 2002, 2003). They possess interesting optoelectronic properties useful for application in light-emitting diodes and photocells (Wilson et al., 2000, 2001). Precursors to these species, such as the title compound, are studied as models of the molecular and electronic properties and structure-property relationships in the metal poly-ynes.

The structure of (I) exhibits a C—H···N close contact between alkynyl atom H25a and N1, with a C25···N1 distance of 3.674 (5) Å (Table 2).

Experimental top

The title compound was synthesized by the following procedure. To a stirred solution of trans-[(PⁿBu₃)₂PtCl₂] (0.38 g, 0.5 mmol) and 3-ethynylcarbazole (0.19 g, 1.0 mmol) in CH₂Cl₂/ⁱPr₂NH (50 ml, 1:1 v/v) under nitrogen was added a catalytic amount of CuI (5 mg). The yellow solution was stirred at room temperature for 15 h, after which all volatile components were removed under reduced pressure. The residue was dissolved in CH₂Cl₂ and passed through a silica column eluting with hexane/CH₂Cl₂ (1:1, v/v). Removal of the solvents under vacuo gave the title complex as a pale-yellow solid in 72% yield.

Structure description top

The structure of (I) exhibits a C—H···N close contact between alkynyl atom H25a and N1, with a C25···N1 distance of 3.674 (5) Å (Table 2).

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), X-SEED (Barbour, 1999) and POV-RAY for Windows (Cason, 1999); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of compound (I), showing the close intermolecular contact between atoms N1 and H25a.

(I) top

Crystal data top

[Pt(C₁₂H₂₇P)₂(C₁₄H₈N)₂]	F(000) = 1008
M_r = 980.13	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 9.2860 (1) Å	Cell parameters from 25483 reflections
b = 19.4330 (3) Å	θ = 2.9–27.5°
c = 13.6980 (2) Å	µ = 3.03 mm⁻¹
β = 104.238 (1)°	T = 150 K
V = 2395.94 (6) Å³	Block, white
Z = 2	0.33 × 0.25 × 0.13 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	3270 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.070
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	θ_max = 25.0°, θ_min = 3.9°
T_min = 0.538, T_max = 0.683	h = −11→11
35095 measured reflections	k = −23→23
4221 independent reflections	l = −16→16

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0312P)² + 0.9277P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.024	(Δ/σ)_max < 0.001
wR(F²) = 0.062	Δρ_max = 0.70 e Å⁻³
S = 1.03	Δρ_min = −1.32 e Å⁻³
4221 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
260 parameters	Extinction coefficient: 0.0016 (3)
0 restraints

Crystal data top

[Pt(C₁₂H₂₇P)₂(C₁₄H₈N)₂]	V = 2395.94 (6) Å³
M_r = 980.13	Z = 2
Monoclinic, P2₁/a	Mo Kα radiation
a = 9.2860 (1) Å	µ = 3.03 mm⁻¹
b = 19.4330 (3) Å	T = 150 K
c = 13.6980 (2) Å	0.33 × 0.25 × 0.13 mm
β = 104.238 (1)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4221 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3270 reflections with I > 2σ(I)
T_min = 0.538, T_max = 0.683	R_int = 0.070
35095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.03	Δρ_max = 0.70 e Å⁻³
4221 reflections	Δρ_min = −1.32 e Å⁻³
260 parameters

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

	x	y	z	U_iso*/U_eq
C1	−0.9298 (4)	0.1955 (2)	−0.5822 (3)	0.0479 (10)
H1	−1.0071	0.2058	−0.64	0.057*
C2	−0.9142 (4)	0.23525 (19)	−0.4978 (3)	0.0439 (10)
H2	−0.9795	0.2726	−0.4961	0.053*
C3	−0.7997 (4)	0.21912 (16)	−0.4149 (2)	0.0319 (8)
C4	−0.7016 (3)	0.16412 (15)	−0.4165 (2)	0.0277 (7)
C5	−0.7203 (4)	0.12433 (18)	−0.5033 (2)	0.0371 (8)
H5	−0.6552	0.087	−0.5059	0.044*
C6	−0.8352 (4)	0.1400 (2)	−0.5858 (3)	0.0449 (9)
H6	−0.8498	0.113	−0.6452	0.054*
C7	−0.6357 (3)	0.21772 (15)	−0.2628 (2)	0.0264 (7)
C8	−0.5550 (4)	0.23210 (15)	−0.1652 (2)	0.0298 (8)
H8	−0.5814	0.2693	−0.1281	0.036*
C9	−0.4354 (4)	0.19049 (15)	−0.1244 (2)	0.0291 (7)
H9	−0.3792	0.1997	−0.0578	0.035*
C10	−0.3925 (3)	0.13462 (15)	−0.1770 (2)	0.0260 (7)
C11	−0.4738 (3)	0.12194 (15)	−0.2752 (2)	0.0240 (7)
H11	−0.4462	0.0852	−0.3125	0.029*
C12	−0.5956 (3)	0.16302 (15)	−0.3189 (2)	0.0247 (7)
C13	−0.2679 (4)	0.09229 (16)	−0.1272 (2)	0.0268 (7)
C14	−0.1660 (4)	0.05812 (16)	−0.0815 (2)	0.0281 (7)
C15	0.3196 (3)	0.07956 (16)	−0.0225 (2)	0.0304 (7)
H15A	0.3695	0.0518	0.0368	0.036*
H15B	0.3913	0.0861	−0.0645	0.036*
C16	0.2821 (4)	0.15066 (16)	0.0146 (2)	0.0349 (8)
H16A	0.3763	0.1759	0.0412	0.042*
H16B	0.2242	0.1768	−0.0441	0.042*
C17	0.1956 (4)	0.15002 (19)	0.0951 (3)	0.0428 (9)
H17A	0.0915	0.1367	0.0639	0.051*
H17B	0.2386	0.1147	0.146	0.051*
C18	0.1964 (6)	0.2188 (2)	0.1472 (3)	0.0672 (14)
H18A	0.139	0.2152	0.1982	0.101*
H18B	0.1518	0.2538	0.0975	0.101*
H18C	0.299	0.2318	0.1797	0.101*
C19	0.2441 (4)	−0.04446 (15)	−0.1407 (2)	0.0278 (7)
H19A	0.3005	−0.0706	−0.0815	0.033*
H19B	0.1625	−0.0745	−0.1774	0.033*
C20	0.3479 (4)	−0.03028 (19)	−0.2099 (2)	0.0319 (7)
H20A	0.2944	−0.0021	−0.2677	0.038*
H20B	0.4342	−0.0033	−0.1723	0.038*
C21	0.4034 (4)	−0.09568 (17)	−0.2492 (3)	0.0371 (8)
H21A	0.3175	−0.122	−0.2888	0.044*
H21B	0.4542	−0.1246	−0.1914	0.044*
C22	0.5103 (4)	−0.0809 (2)	−0.3149 (3)	0.0497 (10)
H22A	0.5432	−0.1243	−0.3385	0.075*
H22B	0.5966	−0.0556	−0.2755	0.075*
H22C	0.4599	−0.053	−0.3729	0.075*
C23	0.0899 (4)	0.08302 (16)	−0.2067 (2)	0.0283 (7)
H23A	0.0405	0.124	−0.1869	0.034*
H23B	0.1748	0.0994	−0.2321	0.034*
C24	−0.0199 (4)	0.04668 (17)	−0.2924 (2)	0.0333 (8)
H24A	0.0286	0.0059	−0.3137	0.04*
H24B	−0.1061	0.0305	−0.2682	0.04*
C25	−0.0734 (5)	0.0940 (2)	−0.3816 (3)	0.0507 (10)
H25A	−0.1147	0.1362	−0.3584	0.061*
H25B	0.013	0.1079	−0.4075	0.061*
C26	−0.1896 (5)	0.0629 (2)	−0.4668 (3)	0.0650 (12)
H26A	−0.2185	0.0966	−0.5215	0.098*
H26B	−0.2769	0.0502	−0.4426	0.098*
H26C	−0.1491	0.0218	−0.4918	0.098*
N1	−0.7591 (3)	0.25035 (14)	−0.3214 (2)	0.0336 (7)
H1A	−0.8049	0.2856	−0.3021	0.04*
P1	0.16139 (9)	0.03072 (5)	−0.09511 (6)	0.02533 (19)
Pt1	0	0	0	0.02389 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.034 (2)	0.074 (3)	0.034 (2)	0.011 (2)	0.0037 (17)	0.0149 (19)
C2	0.033 (2)	0.055 (2)	0.046 (2)	0.0192 (18)	0.0154 (18)	0.0157 (18)
C3	0.0259 (19)	0.0358 (19)	0.0375 (19)	0.0058 (15)	0.0141 (16)	0.0086 (15)
C4	0.0228 (18)	0.0307 (17)	0.0322 (18)	0.0022 (14)	0.0117 (15)	0.0055 (14)
C5	0.031 (2)	0.045 (2)	0.038 (2)	0.0060 (16)	0.0135 (17)	0.0011 (16)
C6	0.037 (2)	0.063 (3)	0.035 (2)	0.005 (2)	0.0087 (18)	−0.0016 (18)
C7	0.0235 (18)	0.0253 (17)	0.0337 (18)	0.0048 (14)	0.0132 (15)	0.0081 (14)
C8	0.033 (2)	0.0269 (17)	0.0342 (19)	0.0013 (15)	0.0181 (16)	0.0000 (14)
C9	0.031 (2)	0.0305 (18)	0.0275 (17)	−0.0075 (15)	0.0104 (15)	0.0005 (14)
C10	0.0216 (18)	0.0267 (17)	0.0332 (18)	−0.0030 (14)	0.0137 (15)	0.0064 (14)
C11	0.0224 (18)	0.0226 (16)	0.0310 (18)	0.0005 (13)	0.0144 (15)	0.0023 (13)
C12	0.0215 (18)	0.0257 (16)	0.0297 (17)	−0.0009 (13)	0.0118 (14)	0.0052 (13)
C13	0.0231 (19)	0.0319 (18)	0.0282 (17)	−0.0034 (15)	0.0114 (15)	0.0057 (14)
C14	0.0260 (19)	0.0338 (18)	0.0275 (17)	−0.0059 (15)	0.0124 (15)	0.0023 (14)
C15	0.0191 (18)	0.0376 (19)	0.0351 (18)	−0.0028 (14)	0.0078 (15)	0.0057 (15)
C16	0.034 (2)	0.0377 (19)	0.0315 (19)	−0.0022 (16)	0.0050 (16)	0.0011 (15)
C17	0.040 (2)	0.050 (2)	0.040 (2)	−0.0012 (18)	0.0136 (18)	−0.0040 (17)
C18	0.112 (4)	0.054 (3)	0.043 (2)	0.009 (3)	0.036 (3)	−0.006 (2)
C19	0.0244 (19)	0.0306 (19)	0.0323 (18)	0.0010 (14)	0.0144 (15)	0.0044 (14)
C20	0.0264 (19)	0.0387 (18)	0.0328 (18)	0.0046 (16)	0.0119 (15)	0.0058 (16)
C21	0.032 (2)	0.044 (2)	0.037 (2)	0.0052 (16)	0.0118 (17)	0.0017 (16)
C22	0.046 (3)	0.064 (3)	0.045 (2)	0.012 (2)	0.024 (2)	0.000 (2)
C23	0.0248 (19)	0.0322 (18)	0.0297 (17)	0.0006 (14)	0.0101 (15)	0.0075 (14)
C24	0.027 (2)	0.041 (2)	0.0347 (19)	0.0006 (15)	0.0129 (16)	0.0026 (15)
C25	0.050 (3)	0.050 (2)	0.043 (2)	0.002 (2)	−0.005 (2)	0.0085 (18)
C26	0.060 (3)	0.079 (3)	0.046 (2)	−0.002 (2)	−0.006 (2)	0.010 (2)
N1	0.0332 (17)	0.0329 (15)	0.0386 (17)	0.0138 (13)	0.0162 (14)	0.0040 (13)
P1	0.0195 (4)	0.0297 (4)	0.0283 (4)	−0.0002 (4)	0.0089 (4)	0.0053 (4)
Pt1	0.01673 (11)	0.03025 (12)	0.02588 (12)	0.00045 (8)	0.00753 (7)	0.00580 (8)

Geometric parameters (Å, º) top

C1—C2	1.369 (5)	C17—H17B	0.99
C1—C6	1.398 (5)	C18—H18A	0.98
C1—H1	0.95	C18—H18B	0.98
C2—C3	1.388 (5)	C18—H18C	0.98
C2—H2	0.95	C19—C20	1.534 (4)
C3—N1	1.383 (4)	C19—P1	1.830 (3)
C3—C4	1.408 (4)	C19—H19A	0.99
C4—C5	1.393 (4)	C19—H19B	0.99
C4—C12	1.453 (4)	C20—C21	1.519 (5)
C5—C6	1.384 (5)	C20—H20A	0.99
C5—H5	0.95	C20—H20B	0.99
C6—H6	0.95	C21—C22	1.522 (5)
C7—N1	1.381 (4)	C21—H21A	0.99
C7—C8	1.391 (4)	C21—H21B	0.99
C7—C12	1.414 (4)	C22—H22A	0.98
C8—C9	1.376 (4)	C22—H22B	0.98
C8—H8	0.95	C22—H22C	0.98
C9—C10	1.414 (4)	C23—C24	1.525 (4)
C9—H9	0.95	C23—P1	1.819 (3)
C10—C11	1.393 (4)	C23—H23A	0.99
C10—C13	1.447 (4)	C23—H23B	0.99
C11—C12	1.393 (4)	C24—C25	1.513 (4)
C11—H11	0.95	C24—H24A	0.99
C13—C14	1.199 (4)	C24—H24B	0.99
C14—Pt1	2.013 (3)	C25—C26	1.508 (5)
C15—C16	1.541 (4)	C25—H25A	0.99
C15—P1	1.825 (3)	C25—H25B	0.99
C15—H15A	0.99	C26—H26A	0.98
C15—H15B	0.99	C26—H26B	0.98
C16—C17	1.516 (5)	C26—H26C	0.98
C16—H16A	0.99	N1—H1A	0.88
C16—H16B	0.99	P1—Pt1	2.2935 (8)
C17—C18	1.514 (5)	Pt1—C14ⁱ	2.013 (3)
C17—H17A	0.99	Pt1—P1ⁱ	2.2935 (8)

C2—C1—C6	121.9 (3)	C20—C19—H19A	108.1
C2—C1—H1	119.1	P1—C19—H19A	108.1
C6—C1—H1	119.1	C20—C19—H19B	108.1
C1—C2—C3	117.7 (3)	P1—C19—H19B	108.1
C1—C2—H2	121.2	H19A—C19—H19B	107.3
C3—C2—H2	121.2	C21—C20—C19	112.8 (3)
N1—C3—C2	129.7 (3)	C21—C20—H20A	109
N1—C3—C4	108.5 (3)	C19—C20—H20A	109
C2—C3—C4	121.8 (3)	C21—C20—H20B	109
C5—C4—C3	119.3 (3)	C19—C20—H20B	109
C5—C4—C12	133.8 (3)	H20A—C20—H20B	107.8
C3—C4—C12	106.9 (3)	C20—C21—C22	112.2 (3)
C6—C5—C4	118.9 (3)	C20—C21—H21A	109.2
C6—C5—H5	120.5	C22—C21—H21A	109.2
C4—C5—H5	120.5	C20—C21—H21B	109.2
C5—C6—C1	120.4 (3)	C22—C21—H21B	109.2
C5—C6—H6	119.8	H21A—C21—H21B	107.9
C1—C6—H6	119.8	C21—C22—H22A	109.5
N1—C7—C8	129.8 (3)	C21—C22—H22B	109.5
N1—C7—C12	108.7 (3)	H22A—C22—H22B	109.5
C8—C7—C12	121.5 (3)	C21—C22—H22C	109.5
C9—C8—C7	117.6 (3)	H22A—C22—H22C	109.5
C9—C8—H8	121.2	H22B—C22—H22C	109.5
C7—C8—H8	121.2	C24—C23—P1	115.1 (2)
C8—C9—C10	123.0 (3)	C24—C23—H23A	108.5
C8—C9—H9	118.5	P1—C23—H23A	108.5
C10—C9—H9	118.5	C24—C23—H23B	108.5
C11—C10—C9	118.3 (3)	P1—C23—H23B	108.5
C11—C10—C13	122.4 (3)	H23A—C23—H23B	107.5
C9—C10—C13	119.3 (3)	C25—C24—C23	111.4 (3)
C10—C11—C12	120.2 (3)	C25—C24—H24A	109.4
C10—C11—H11	119.9	C23—C24—H24A	109.4
C12—C11—H11	119.9	C25—C24—H24B	109.4
C11—C12—C7	119.4 (3)	C23—C24—H24B	109.4
C11—C12—C4	134.3 (3)	H24A—C24—H24B	108
C7—C12—C4	106.3 (3)	C26—C25—C24	114.3 (3)
C14—C13—C10	176.7 (3)	C26—C25—H25A	108.7
C13—C14—Pt1	177.5 (3)	C24—C25—H25A	108.7
C16—C15—P1	115.4 (2)	C26—C25—H25B	108.7
C16—C15—H15A	108.4	C24—C25—H25B	108.7
P1—C15—H15A	108.4	H25A—C25—H25B	107.6
C16—C15—H15B	108.4	C25—C26—H26A	109.5
P1—C15—H15B	108.4	C25—C26—H26B	109.5
H15A—C15—H15B	107.5	H26A—C26—H26B	109.5
C17—C16—C15	115.8 (3)	C25—C26—H26C	109.5
C17—C16—H16A	108.3	H26A—C26—H26C	109.5
C15—C16—H16A	108.3	H26B—C26—H26C	109.5
C17—C16—H16B	108.3	C7—N1—C3	109.5 (3)
C15—C16—H16B	108.3	C7—N1—H1A	125.2
H16A—C16—H16B	107.4	C3—N1—H1A	125.2
C18—C17—C16	113.2 (3)	C23—P1—C15	104.23 (14)
C18—C17—H17A	108.9	C23—P1—C19	104.85 (15)
C16—C17—H17A	108.9	C15—P1—C19	104.61 (15)
C18—C17—H17B	108.9	C23—P1—Pt1	117.91 (11)
C16—C17—H17B	108.9	C15—P1—Pt1	112.13 (11)
H17A—C17—H17B	107.8	C19—P1—Pt1	111.94 (10)
C17—C18—H18A	109.5	C14ⁱ—Pt1—C14	180.0 (3)
C17—C18—H18B	109.5	C14ⁱ—Pt1—P1	86.70 (8)
H18A—C18—H18B	109.5	C14—Pt1—P1	93.30 (8)
C17—C18—H18C	109.5	C14ⁱ—Pt1—P1ⁱ	93.30 (8)
H18A—C18—H18C	109.5	C14—Pt1—P1ⁱ	86.70 (8)
H18B—C18—H18C	109.5	P1—Pt1—P1ⁱ	180.00 (5)
C20—C19—P1	116.6 (2)

C6—C1—C2—C3	0.4 (6)	P1—C15—C16—C17	68.8 (3)
C1—C2—C3—N1	179.9 (3)	C15—C16—C17—C18	165.1 (3)
C1—C2—C3—C4	0.3 (5)	P1—C19—C20—C21	−176.4 (2)
N1—C3—C4—C5	179.8 (3)	C19—C20—C21—C22	−178.1 (3)
C2—C3—C4—C5	−0.5 (5)	P1—C23—C24—C25	179.9 (3)
N1—C3—C4—C12	−0.6 (3)	C23—C24—C25—C26	−176.4 (3)
C2—C3—C4—C12	179.0 (3)	C8—C7—N1—C3	178.6 (3)
C3—C4—C5—C6	0.0 (5)	C12—C7—N1—C3	−0.9 (3)
C12—C4—C5—C6	−179.4 (3)	C2—C3—N1—C7	−178.7 (3)
C4—C5—C6—C1	0.7 (5)	C4—C3—N1—C7	1.0 (3)
C2—C1—C6—C5	−0.9 (6)	C24—C23—P1—C15	166.1 (2)
N1—C7—C8—C9	179.8 (3)	C24—C23—P1—C19	56.4 (3)
C12—C7—C8—C9	−0.8 (4)	C24—C23—P1—Pt1	−68.9 (2)
C7—C8—C9—C10	−0.1 (5)	C16—C15—P1—C23	63.2 (3)
C8—C9—C10—C11	1.0 (4)	C16—C15—P1—C19	173.0 (2)
C8—C9—C10—C13	−178.2 (3)	C16—C15—P1—Pt1	−65.5 (2)
C9—C10—C11—C12	−1.0 (4)	C20—C19—P1—C23	47.9 (3)
C13—C10—C11—C12	178.2 (3)	C20—C19—P1—C15	−61.4 (3)
C10—C11—C12—C7	0.1 (4)	C20—C19—P1—Pt1	176.9 (2)
C10—C11—C12—C4	180.0 (3)	C13—C14—Pt1—C14ⁱ	92 (72)
N1—C7—C12—C11	−179.7 (3)	C13—C14—Pt1—P1	−170 (7)
C8—C7—C12—C11	0.8 (4)	C13—C14—Pt1—P1ⁱ	10 (7)
N1—C7—C12—C4	0.5 (3)	C23—P1—Pt1—C14ⁱ	174.09 (15)
C8—C7—C12—C4	−179.0 (3)	C15—P1—Pt1—C14ⁱ	−64.87 (14)
C5—C4—C12—C11	−0.3 (6)	C19—P1—Pt1—C14ⁱ	52.35 (15)
C3—C4—C12—C11	−179.7 (3)	C23—P1—Pt1—C14	−5.91 (15)
C5—C4—C12—C7	179.6 (3)	C15—P1—Pt1—C14	115.13 (14)
C3—C4—C12—C7	0.1 (3)	C19—P1—Pt1—C14	−127.65 (15)
C11—C10—C13—C14	−153 (6)	C23—P1—Pt1—P1ⁱ	85 (31)
C9—C10—C13—C14	26 (6)	C15—P1—Pt1—P1ⁱ	−154 (31)
C10—C13—C14—Pt1	31 (11)	C19—P1—Pt1—P1ⁱ	−36 (31)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25A···N1ⁱⁱ	0.99	2.69	3.674 (5)	171

Symmetry code: (ii) x+1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Pt(C₁₂H₂₇P)₂(C₁₄H₈N)₂]
M_r	980.13
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	150
a, b, c (Å)	9.2860 (1), 19.4330 (3), 13.6980 (2)
β (°)	104.238 (1)
V (Å³)	2395.94 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.03
Crystal size (mm)	0.33 × 0.25 × 0.13

Data collection
Diffractometer	Bruker–Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.538, 0.683
No. of measured, independent and observed [I > 2σ(I)] reflections	35095, 4221, 3270
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.062, 1.03
No. of reflections	4221
No. of parameters	260
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −1.32

Computer programs: COLLECT (Nonius, 1997), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), X-SEED (Barbour, 1999) and POV-RAY for Windows (Cason, 1999), WinGX publication routines (Farrugia, 1999).

Selected geometric parameters (Å, º) top

C3—N1	1.383 (4)	C13—C14	1.199 (4)
C3—C4	1.408 (4)	C14—Pt1	2.013 (3)
C4—C12	1.453 (4)	C15—P1	1.825 (3)
C7—N1	1.381 (4)	C19—P1	1.830 (3)
C7—C12	1.414 (4)	C23—P1	1.819 (3)
C10—C13	1.447 (4)	P1—Pt1	2.2935 (8)

N1—C3—C4	108.5 (3)	C7—N1—C3	109.5 (3)
C3—C4—C12	106.9 (3)	C23—P1—Pt1	117.91 (11)
N1—C7—C12	108.7 (3)	C15—P1—Pt1	112.13 (11)
C7—C12—C4	106.3 (3)	C19—P1—Pt1	111.94 (10)
C14—C13—C10	176.7 (3)	C14—Pt1—P1	93.30 (8)
C13—C14—Pt1	177.5 (3)

N1—C3—C4—C12	−0.6 (3)	C4—C3—N1—C7	1.0 (3)
C8—C9—C10—C13	−178.2 (3)	C13—C14—Pt1—P1	−170 (7)
N1—C7—C12—C4	0.5 (3)	C23—P1—Pt1—C14	−5.91 (15)
C3—C4—C12—C7	0.1 (3)	C15—P1—Pt1—C14	115.13 (14)
C12—C7—N1—C3	−0.9 (3)	C19—P1—Pt1—C14	−127.65 (15)