Chloridonitros­yl[meso-5,10,15,20-tetra­kis­(p-tol­yl)porphyrinato-κ4N,N′,N′′,N′′′]osmium(II) tetra­hydro­furan tetra­solvate

Chen, L.; Xu, N.; Powell, D.R.; Richter-Addo, G.B.

doi:10.1107/S1600536811001401

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m224

doi:10.1107/S1600536811001401

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Chloridonitrosyl[meso-5,10,15,20-tetrakis(p-tolyl)porphyrinato-κ⁴N,N′,N′′,N′′′]osmium(II) tetrahydrofuran tetrasolvate

Li Chen,^a Nan Xu,^a ^* Douglas R. Powell ^a and George B. Richter-Addo ^a

^aDepartment of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Parkway, Norman, OK 73019-5251, USA
^*Correspondence e-mail: xunan@ou.edu

(Received 3 January 2011; accepted 10 January 2011; online 22 January 2011)

The title compound, [OsCl(NO)(C₄₈H₃₆N₄)]·4C₄H₈O, is a six-coordinate osmium(II) porphyrin complex with nitrosyl (NO) and chloride (Cl) ligands trans to each other in an octahedral geometry. The metal complex lies on a fourfold rotation axis that passes through the Os, N, O and Cl atoms. The NO and Cl ligands are disordered in an 0.511 (12):0.486 (12) ratio.

Related literature

For related osmium nitrosyl porphyrin derivatives, see: Cheng et al. (2001 ); Lee et al. (2001 ). For the synthesis, see: Cheng et al. (1998 ).

Experimental

Crystal data

[OsCl(NO)(C₄₈H₃₆N₄)]·4C₄H₈O
M_r = 1212.88
Tetragonal, P 4/n
a = 16.905 (2) Å
c = 9.6220 (19) Å
V = 2749.8 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.42 mm⁻¹
T = 188 K
0.62 × 0.58 × 0.52 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.315, T_max = 0.366
8309 measured reflections
2859 independent reflections
2749 reflections with I > 2σ(I)
R_int = 0.024
3 standard reflections every 97 reflections intensity decay: 6.7%

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.058
S = 0.97
2859 reflections
187 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −1.46 e Å⁻³

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001401/ng5100sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001401/ng5100Isup2.hkl

checkCIF report

Comment top

Six-coordinate osmium nitrosyl porphyrin complexes have been prepared as potential heme-NO structural models (Cheng et al. 2001 and Lee et al. 2001). Compared to their iron derivatives, osmium nitrosyl porphyrin compounds are more thermally stable and more easily characterized spectroscopically. In this paper, we report the structure of (chloro)(nitrosyl)(meso-5,10,15,20-tetrakis(p-tolyl)porphyrinato)osmium with four molecules of tetrahydrofuran as the solvate.

The metal complex is found to sit on a crystallographic 4 axis. The nitrosyl and chloride ligands are disordered across the porphyrin plane. The occupancies of the nitrosyl and chloride ligands refine to 0.511 (12) and 0.486 (12) for the unprimed and primed atoms, respectively. The molecular structure of (TTP)Os(NO)Cl is shown in Figure 1. The nitrosyl group binds to the osmium center through its nitrogen atom, exhibiting a linear Os—N—O conformation (180°). The average Os—N_p distance is 2.0622 (19) Å. The average Os—N(O) distance is 1.80 (3) Å and the average Os—Cl distance is 2.208 (8) Å. The average N—O distance is 1.244 (2) Å.

Related literature top

For related osmium nitrosyl porphyrin derivatives, see: Cheng et al. (2001); Lee et al. (2001). For the synthesis, see: Cheng et al. (1998).

Experimental top

The titled compound was obtained as a sideproduct during the preparation of (TTP)Os(NO)(Me) from the reaction of [(TTP)Os(NO)]PF₆ with MeMgCl in THF (Cheng et al. 1998), and crystals were obtained by slow evaporation of a THF-hexane (1:1) solution at room temperature.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (TTP)Os(NO)Cl^.4THF. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.

Chloridonitrosyl[meso-5,10,15,20-tetrakis(p-tolyl)porphyrinato- κ⁴N,N',N'',N''')osmium(II) tetrahydrofuran tetrasolvate top

Crystal data top

[OsCl(NO)(C₄₈H₃₆N₄)]·4C₄H₈O	D_x = 1.465 Mg m⁻³
M_r = 1212.88	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4/n	Cell parameters from 41 reflections
Hall symbol: -P 4a	θ = 6.9–12.4°
a = 16.905 (2) Å	µ = 2.42 mm⁻¹
c = 9.6220 (19) Å	T = 188 K
V = 2749.8 (8) Å³	Block, purple
Z = 2	0.62 × 0.58 × 0.52 mm
F(000) = 1240

Data collection top

Siemens P4 diffractometer	2749 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 26.5°, θ_min = 2.1°
ω scans	h = −1→21
Absorption correction: ψ scan (North et al., 1968)	k = −14→21
T_min = 0.315, T_max = 0.366	l = −12→12
8309 measured reflections	3 standard reflections every 97 reflections
2859 independent reflections	intensity decay: 6.7%

Refinement top

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)] = 0.022	H-atom parameters constrained
wR(F²) = 0.058	w = 1/[σ²(F_o²) + (0.040P)² + 0.950P] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
2859 reflections	Δρ_max = 0.59 e Å⁻³
187 parameters	Δρ_min = −1.46 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00138 (16)

Crystal data top

[OsCl(NO)(C₄₈H₃₆N₄)]·4C₄H₈O	Z = 2
M_r = 1212.88	Mo Kα radiation
Tetragonal, P4/n	µ = 2.42 mm⁻¹
a = 16.905 (2) Å	T = 188 K
c = 9.6220 (19) Å	0.62 × 0.58 × 0.52 mm
V = 2749.8 (8) Å³

Data collection top

Siemens P4 diffractometer	2749 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.024
T_min = 0.315, T_max = 0.366	3 standard reflections every 97 reflections
8309 measured reflections	intensity decay: 6.7%
2859 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	1 restraint
wR(F²) = 0.058	H-atom parameters constrained
S = 0.97	Δρ_max = 0.59 e Å⁻³
2859 reflections	Δρ_min = −1.46 e Å⁻³
187 parameters

Special details top

Refinement. Restraint: sump 0.25 0.0004 1 2 1 3 where the second and third item on the fvar instruction were occupancies of N2, O1, Cl1, and N2', O1', and Cl1', respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Os1	0.2500	0.2500	0.764201 (16)	0.02581 (8)
N1	0.35454 (11)	0.31287 (11)	0.76484 (15)	0.0223 (3)
C1	0.42941 (13)	0.28109 (14)	0.76543 (17)	0.0245 (4)
C2	0.48571 (14)	0.34489 (15)	0.76709 (19)	0.0298 (5)
H2	0.5417	0.3397	0.7685	0.036*
C3	0.44474 (14)	0.41381 (15)	0.76625 (19)	0.0294 (5)
H3	0.4666	0.4656	0.7661	0.035*
C4	0.36169 (14)	0.39376 (13)	0.76565 (18)	0.0245 (4)
C5	0.44808 (13)	0.20028 (14)	0.76528 (17)	0.0246 (4)
C6	0.53430 (14)	0.17924 (14)	0.76365 (18)	0.0254 (4)
C7	0.57898 (12)	0.19002 (13)	0.6443 (2)	0.0308 (4)
H7	0.5545	0.2103	0.5629	0.037*
C8	0.65901 (12)	0.17163 (13)	0.6424 (2)	0.0318 (5)
H8	0.6883	0.1787	0.5591	0.038*
C9	0.69700 (14)	0.14299 (15)	0.76017 (18)	0.0279 (5)
C10	0.65179 (13)	0.13145 (14)	0.8786 (2)	0.0361 (5)
H10	0.6761	0.1112	0.9602	0.043*
C11	0.57146 (12)	0.14902 (14)	0.8803 (2)	0.0350 (5)
H11	0.5417	0.1402	0.9625	0.042*
C12	0.78439 (16)	0.12540 (19)	0.7586 (2)	0.0390 (6)
H12A	0.7967	0.0865	0.8309	0.058*
H12B	0.8140	0.1742	0.7763	0.058*
H12C	0.7993	0.1041	0.6676	0.058*
N2	0.2500	0.2500	0.5792 (16)	0.031 (4)	0.511 (12)
O1	0.2500	0.2500	0.4507 (15)	0.057 (2)	0.511 (12)
Cl1	0.2500	0.2500	0.9929 (8)	0.031 (2)	0.511 (12)
N2'	0.2500	0.2500	0.953 (3)	0.040 (8)	:0.486 (12)
O1'	0.2500	0.2500	1.0823 (14)	0.048 (2)	0.486 (12)
Cl1'	0.2500	0.2500	0.5339 (5)	0.0303 (18)	0.486 (12)
O1S	0.39867 (19)	0.45886 (16)	0.2341 (2)	0.0674 (7)
C1S	0.3997 (2)	0.4362 (2)	0.3748 (3)	0.0680 (9)
H1SA	0.3451	0.4329	0.4117	0.082*
H1SB	0.4297	0.4750	0.4308	0.082*
C2S	0.43853 (19)	0.3572 (2)	0.3803 (3)	0.0657 (8)
H2SA	0.4198	0.3261	0.4610	0.079*
H2SB	0.4968	0.3622	0.3847	0.079*
C3S	0.4123 (3)	0.3206 (2)	0.2450 (3)	0.0567 (8)
H3SA	0.4515	0.2817	0.2109	0.068*
H3SB	0.3603	0.2944	0.2548	0.068*
C4S	0.40732 (18)	0.39121 (18)	0.1500 (3)	0.0550 (7)
H4SA	0.4559	0.3954	0.0931	0.066*
H4SB	0.3614	0.3859	0.0867	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Os1	0.01638 (8)	0.01638 (8)	0.04466 (12)	0.000	0.000	0.000
N1	0.0171 (8)	0.0180 (8)	0.0317 (8)	−0.0005 (7)	−0.0002 (5)	0.0002 (5)
C1	0.0190 (10)	0.0258 (11)	0.0287 (9)	−0.0003 (8)	−0.0006 (6)	−0.0003 (7)
C2	0.0227 (11)	0.0288 (12)	0.0381 (11)	−0.0019 (9)	−0.0003 (7)	−0.0016 (7)
C3	0.0249 (11)	0.0264 (11)	0.0369 (11)	−0.0050 (9)	0.0009 (7)	−0.0010 (7)
C4	0.0244 (11)	0.0202 (10)	0.0288 (9)	−0.0035 (8)	0.0008 (7)	−0.0008 (6)
C5	0.0195 (10)	0.0265 (11)	0.0278 (9)	0.0015 (8)	−0.0005 (6)	−0.0004 (7)
C6	0.0204 (10)	0.0231 (11)	0.0326 (10)	0.0001 (8)	−0.0017 (7)	−0.0027 (7)
C7	0.0261 (10)	0.0356 (11)	0.0308 (9)	0.0044 (9)	−0.0012 (7)	0.0059 (8)
C8	0.0259 (10)	0.0370 (12)	0.0324 (10)	0.0024 (9)	0.0043 (7)	0.0051 (8)
C9	0.0207 (11)	0.0267 (12)	0.0363 (11)	0.0023 (9)	−0.0014 (7)	−0.0016 (7)
C10	0.0283 (11)	0.0491 (14)	0.0309 (10)	0.0070 (10)	−0.0048 (8)	0.0054 (9)
C11	0.0259 (10)	0.0500 (14)	0.0292 (10)	0.0044 (9)	0.0020 (8)	0.0035 (9)
C12	0.0240 (12)	0.0486 (17)	0.0443 (13)	0.0071 (11)	−0.0008 (8)	0.0045 (9)
N2	0.034 (4)	0.034 (4)	0.025 (11)	0.000	0.000	0.000
O1	0.077 (5)	0.077 (5)	0.016 (5)	0.000	0.000	0.000
Cl1	0.0298 (11)	0.0298 (11)	0.032 (6)	0.000	0.000	0.000
N2'	0.039 (5)	0.039 (5)	0.04 (2)	0.000	0.000	0.000
O1'	0.065 (4)	0.065 (4)	0.015 (5)	0.000	0.000	0.000
Cl1'	0.0354 (10)	0.0354 (10)	0.020 (5)	0.000	0.000	0.000
O1S	0.0723 (18)	0.0438 (14)	0.0861 (17)	0.0008 (13)	−0.0012 (11)	0.0023 (9)
C1S	0.0578 (19)	0.077 (2)	0.0693 (19)	0.0008 (16)	0.0034 (15)	−0.0246 (17)
C2S	0.0583 (19)	0.089 (2)	0.0504 (16)	0.0095 (16)	−0.0073 (13)	0.0021 (15)
C3S	0.060 (2)	0.0456 (19)	0.0643 (19)	0.0071 (17)	−0.0055 (12)	−0.0029 (11)
C4S	0.0531 (17)	0.0637 (19)	0.0480 (14)	−0.0037 (14)	−0.0013 (12)	0.0037 (12)

Geometric parameters (Å, º) top

Os1—N2	1.780 (16)	C9—C12	1.507 (3)
Os1—N2'	1.81 (3)	C10—C11	1.390 (3)
Os1—N1ⁱ	2.0622 (19)	C10—H10	0.9500
Os1—N1	2.0622 (19)	C11—H11	0.9500
Os1—Cl1	2.201 (8)	C12—H12A	0.9800
Os1—Cl1'	2.216 (8)	C12—H12B	0.9800
N1—C4	1.373 (3)	C12—H12C	0.9800
N1—C1	1.375 (3)	N2—O1	1.237 (16)
C1—C5	1.402 (3)	N2'—O1'	1.25 (2)
C1—C2	1.439 (3)	O1S—C1S	1.407 (4)
C2—C3	1.355 (4)	O1S—C4S	1.408 (4)
C2—H2	0.9500	C1S—C2S	1.488 (5)
C3—C4	1.444 (3)	C1S—H1SA	0.9900
C3—H3	0.9500	C1S—H1SB	0.9900
C4—C5ⁱ	1.393 (3)	C2S—C3S	1.508 (4)
C5—C6	1.500 (3)	C2S—H2SA	0.9900
C6—C11	1.384 (3)	C2S—H2SB	0.9900
C6—C7	1.386 (3)	C3S—C4S	1.506 (4)
C7—C8	1.388 (3)	C3S—H3SA	0.9900
C7—H7	0.9500	C3S—H3SB	0.9900
C8—C9	1.389 (3)	C4S—H4SA	0.9900
C8—H8	0.9500	C4S—H4SB	0.9900
C9—C10	1.386 (3)

N2—Os1—N1	90.17 (4)	C11—C10—H10	119.4
N2'—Os1—N1	89.83 (4)	C6—C11—C10	120.9 (2)
N1—Os1—N1ⁱⁱ	90.0	C6—C11—H11	119.6
N2'—Os1—Cl1'	180.000 (5)	C10—C11—H11	119.6
N1—Os1—Cl1'	90.17 (4)	C9—C12—H12A	109.5
C4—N1—C1	107.95 (19)	C9—C12—H12B	109.5
C4—N1—Os1	126.07 (15)	H12A—C12—H12B	109.5
C1—N1—Os1	125.98 (15)	C9—C12—H12C	109.5
N1—C1—C5	126.0 (2)	H12A—C12—H12C	109.5
N1—C1—C2	108.4 (2)	H12B—C12—H12C	109.5
C5—C1—C2	125.6 (2)	O1—N2—Os1	180.000 (2)
C3—C2—C1	107.8 (2)	O1'—N2'—Os1	180.000 (4)
C3—C2—H2	126.1	C1S—O1S—C4S	109.3 (2)
C1—C2—H2	126.1	O1S—C1S—C2S	106.5 (2)
C2—C3—C4	107.2 (2)	O1S—C1S—H1SA	110.4
C2—C3—H3	126.4	C2S—C1S—H1SA	110.4
C4—C3—H3	126.4	O1S—C1S—H1SB	110.4
N1—C4—C5ⁱ	126.2 (2)	C2S—C1S—H1SB	110.4
N1—C4—C3	108.6 (2)	H1SA—C1S—H1SB	108.6
C5ⁱ—C4—C3	125.2 (2)	C1S—C2S—C3S	102.0 (3)
C4ⁱⁱ—C5—C1	125.8 (2)	C1S—C2S—H2SA	111.4
C4ⁱⁱ—C5—C6	117.5 (2)	C3S—C2S—H2SA	111.4
C1—C5—C6	116.7 (2)	C1S—C2S—H2SB	111.4
C11—C6—C7	118.2 (2)	C3S—C2S—H2SB	111.4
C11—C6—C5	121.33 (18)	H2SA—C2S—H2SB	109.2
C7—C6—C5	120.45 (18)	C4S—C3S—C2S	102.4 (3)
C6—C7—C8	120.84 (19)	C4S—C3S—H3SA	111.3
C6—C7—H7	119.6	C2S—C3S—H3SA	111.3
C8—C7—H7	119.6	C4S—C3S—H3SB	111.3
C7—C8—C9	121.17 (19)	C2S—C3S—H3SB	111.3
C7—C8—H8	119.4	H3SA—C3S—H3SB	109.2
C9—C8—H8	119.4	O1S—C4S—C3S	107.5 (2)
C10—C9—C8	117.7 (2)	O1S—C4S—H4SA	110.2
C10—C9—C12	121.40 (18)	C3S—C4S—H4SA	110.2
C8—C9—C12	120.91 (18)	O1S—C4S—H4SB	110.2
C9—C10—C11	121.2 (2)	C3S—C4S—H4SB	110.2
C9—C10—H10	119.4	H4SA—C4S—H4SB	108.5

N2—Os1—N1—C4	90.28 (13)	C2—C3—C4—C5ⁱ	179.72 (17)
N2'—Os1—N1—C4	−89.72 (13)	N1—C1—C5—C4ⁱⁱ	−0.5 (3)
N1ⁱ—Os1—N1—C4	0.11 (17)	C2—C1—C5—C4ⁱⁱ	179.04 (17)
N1ⁱⁱ—Os1—N1—C4	−179.55 (11)	N1—C1—C5—C6	179.03 (15)
Cl1—Os1—N1—C4	−89.72 (13)	C2—C1—C5—C6	−1.4 (3)
Cl1'—Os1—N1—C4	90.28 (13)	C4ⁱⁱ—C5—C6—C11	−73.1 (3)
N2—Os1—N1—C1	−90.17 (13)	C1—C5—C6—C11	107.3 (2)
N2'—Os1—N1—C1	89.83 (13)	C4ⁱⁱ—C5—C6—C7	107.2 (2)
N1ⁱ—Os1—N1—C1	179.66 (10)	C1—C5—C6—C7	−72.4 (3)
N1ⁱⁱ—Os1—N1—C1	0.00 (16)	C11—C6—C7—C8	−0.6 (3)
Cl1—Os1—N1—C1	89.83 (13)	C5—C6—C7—C8	179.2 (2)
Cl1'—Os1—N1—C1	−90.17 (13)	C6—C7—C8—C9	−0.9 (3)
C4—N1—C1—C5	179.82 (16)	C7—C8—C9—C10	1.7 (3)
Os1—N1—C1—C5	0.2 (2)	C7—C8—C9—C12	−178.2 (2)
C4—N1—C1—C2	0.18 (19)	C8—C9—C10—C11	−0.9 (3)
Os1—N1—C1—C2	−179.44 (12)	C12—C9—C10—C11	178.9 (2)
N1—C1—C2—C3	−0.5 (2)	C7—C6—C11—C10	1.3 (3)
C5—C1—C2—C3	179.82 (17)	C5—C6—C11—C10	−178.5 (2)
C1—C2—C3—C4	0.6 (2)	C9—C10—C11—C6	−0.5 (4)
C1—N1—C4—C5ⁱ	179.94 (16)	C4S—O1S—C1S—C2S	20.6 (4)
Os1—N1—C4—C5ⁱ	−0.4 (2)	O1S—C1S—C2S—C3S	−33.6 (4)
C1—N1—C4—C3	0.22 (19)	C1S—C2S—C3S—C4S	32.9 (4)
Os1—N1—C4—C3	179.84 (11)	C1S—O1S—C4S—C3S	1.3 (4)
C2—C3—C4—N1	−0.6 (2)	C2S—C3S—C4S—O1S	−22.0 (4)

Symmetry codes: (i) −y+1/2, x, z; (ii) y, −x+1/2, z.

Experimental details

Crystal data
Chemical formula	[OsCl(NO)(C₄₈H₃₆N₄)]·4C₄H₈O
M_r	1212.88
Crystal system, space group	Tetragonal, P4/n
Temperature (K)	188
a, c (Å)	16.905 (2), 9.6220 (19)
V (Å³)	2749.8 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.42
Crystal size (mm)	0.62 × 0.58 × 0.52

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.315, 0.366
No. of measured, independent and observed [I > 2σ(I)] reflections	8309, 2859, 2749
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.058, 0.97
No. of reflections	2859
No. of parameters	187
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −1.46

Computer programs: XSCANS (Siemens, 1994), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the National Institutes of Health (FIRST Award 1R29 GM53586–01 A1) and the National Science Foundation (CAREER Award CHE-9625065) for funding of this research. We thank Dr Masood Khan for assistance with the data collection and Dr Lin Cheng and Hee-Sun Chung for technical assistance.

References

Cheng, L., Chen, L., Chung, H.-S., Khan, M. A., Richter-Addo, G. B. & Young, V. G. Jr (1998). Organometallics, 17, 3853–3864. Web of Science CSD CrossRef CAS Google Scholar
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