Literature DB >> 21578604

[(Z)-N,O-Disopropyl-thio-carbamato-κS](tricyclo-hexyl-phosphine-κP)gold(I).

Primjira P Tadbuppa, Edward R T Tiekink.   

Abstract

In the title compound, [Au(C(7)H(14)NOS)(C(18)H(33)P)], the Au(I) atom is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S-Au-P = 174.94 (2)°], with the distortion due to a short intra-molecular Au⋯O contact [2.908 (2) Å].

Entities:  

Year:  2009        PMID: 21578604      PMCID: PMC2971935          DOI: 10.1107/S1600536809047084

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For structural systematics and luminescence properties of phosphinegold(I) carbonimidothio­ates, see: Ho et al. (2006 ▶); Ho & Tiekink (2007 ▶); Kuan et al. (2008 ▶). For the synthesis, see: Hall et al. (1993 ▶).

Experimental

Crystal data

[Au(C7H14NOS)(C18H33P)] M = 637.63 Triclinic, a = 11.1236 (5) Å b = 11.7949 (6) Å c = 11.9037 (6) Å α = 73.869 (1)° β = 85.282 (1)° γ = 66.515 (1)° V = 1375.30 (12) Å3 Z = 2 Mo Kα radiation μ = 5.50 mm−1 T = 223 K 0.19 × 0.16 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.636, T max = 1 10973 measured reflections 6300 independent reflections 5853 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.021 wR(F 2) = 0.054 S = 0.98 6300 reflections 271 parameters H-atom parameters constrained Δρmax = 1.01 e Å−3 Δρmin = −0.78 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047084/hb5218sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047084/hb5218Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Au(C7H14NOS)(C18H33P)]Z = 2
Mr = 637.63F(000) = 644
Triclinic, P1Dx = 1.540 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 11.1236 (5) ÅCell parameters from 7451 reflections
b = 11.7949 (6) Åθ = 2.2–30.0°
c = 11.9037 (6) ŵ = 5.50 mm1
α = 73.869 (1)°T = 223 K
β = 85.282 (1)°Block, colourless
γ = 66.515 (1)°0.19 × 0.16 × 0.11 mm
V = 1375.30 (12) Å3
Bruker SMART CCD diffractometer6300 independent reflections
Radiation source: fine-focus sealed tube5853 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −14→14
Tmin = 0.636, Tmax = 1k = −15→15
10973 measured reflectionsl = −13→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.0323P)2] where P = (Fo2 + 2Fc2)/3
6300 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 1.01 e Å3
0 restraintsΔρmin = −0.78 e Å3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
Au0.099579 (9)0.244875 (8)−0.000750 (8)0.02575 (4)
S10.17603 (7)0.13648 (7)0.18959 (6)0.03236 (15)
P10.04149 (6)0.33925 (6)−0.19218 (6)0.02396 (13)
O10.30086 (19)−0.01420 (18)0.05751 (16)0.0341 (4)
N10.3452 (2)−0.1149 (2)0.2521 (2)0.0380 (6)
C10.2845 (3)−0.0148 (3)0.1727 (2)0.0302 (6)
C20.3294 (3)−0.1112 (3)0.3740 (3)0.0452 (8)
H20.2426−0.04460.38200.054*
C30.4361 (4)−0.0765 (4)0.4098 (3)0.0602 (10)
H3A0.42760.00760.36140.090*
H3B0.5216−0.13970.39960.090*
H3C0.4270−0.07530.49130.090*
C40.3361 (4)−0.2409 (4)0.4495 (3)0.0616 (11)
H4A0.2668−0.25970.42470.092*
H4B0.3253−0.23910.53070.092*
H4C0.4205−0.30680.44120.092*
C50.3930 (3)−0.1300 (3)0.0295 (3)0.0385 (7)
H50.4687−0.17220.08590.046*
C60.3260 (4)−0.2196 (4)0.0361 (4)0.0618 (11)
H6A0.2994−0.24530.11560.093*
H6B0.3860−0.29500.01330.093*
H6C0.2494−0.1766−0.01630.093*
C70.4384 (3)−0.0863 (3)−0.0916 (3)0.0458 (7)
H7A0.4820−0.0298−0.09090.069*
H7B0.3634−0.0407−0.14590.069*
H7C0.4992−0.1604−0.11590.069*
C80.0941 (3)0.2106 (3)−0.2671 (2)0.0301 (5)
H80.19050.1670−0.25450.036*
C90.0396 (4)0.1087 (3)−0.2087 (3)0.0438 (7)
H9A−0.05620.1465−0.21850.053*
H9B0.06190.0785−0.12470.053*
C100.0966 (4)−0.0041 (3)−0.2628 (4)0.0544 (9)
H10A0.1909−0.0483−0.24370.065*
H10B0.0556−0.0651−0.22870.065*
C110.0755 (4)0.0378 (4)−0.3945 (4)0.0631 (11)
H11A0.1189−0.0367−0.42580.076*
H11B−0.01860.0722−0.41360.076*
C120.1290 (5)0.1389 (4)−0.4514 (3)0.0652 (11)
H12A0.10840.1682−0.53570.078*
H12B0.22460.1018−0.44010.078*
C130.0697 (4)0.2527 (3)−0.3988 (3)0.0509 (8)
H13A0.10830.3154−0.43440.061*
H13B−0.02490.2944−0.41640.061*
C140.1314 (2)0.4419 (2)−0.2571 (2)0.0274 (5)
H140.10620.4802−0.34130.033*
C150.2799 (3)0.3628 (3)−0.2449 (3)0.0393 (7)
H15A0.30390.3165−0.16260.047*
H15B0.30280.2992−0.28970.047*
C160.3585 (3)0.4462 (3)−0.2882 (3)0.0469 (8)
H16A0.45220.3926−0.27360.056*
H16B0.34320.4840−0.37280.056*
C170.3205 (3)0.5522 (3)−0.2277 (3)0.0471 (8)
H17A0.36870.6069−0.26090.057*
H17B0.34500.5144−0.14430.057*
C180.1739 (3)0.6335 (3)−0.2416 (3)0.0449 (8)
H18A0.15080.6788−0.32430.054*
H18B0.15150.6978−0.19760.054*
C190.0950 (3)0.5502 (3)−0.1972 (3)0.0345 (6)
H19A0.00130.6042−0.21140.041*
H19B0.11060.5129−0.11260.041*
C20−0.1345 (2)0.4342 (2)−0.2282 (2)0.0276 (5)
H20−0.17230.3730−0.23460.033*
C21−0.2064 (3)0.4929 (3)−0.1287 (2)0.0329 (6)
H21A−0.19260.4245−0.05590.039*
H21B−0.16980.5519−0.11670.039*
C22−0.3537 (3)0.5655 (3)−0.1575 (3)0.0438 (7)
H22A−0.39200.5046−0.16030.053*
H22B−0.39570.6063−0.09530.053*
C23−0.3806 (3)0.6671 (3)−0.2735 (3)0.0418 (7)
H23A−0.47540.7097−0.29040.050*
H23B−0.34850.7320−0.26900.050*
C24−0.3136 (3)0.6074 (3)−0.3709 (3)0.0467 (8)
H24A−0.33050.6745−0.44500.056*
H24B−0.34990.5466−0.37870.056*
C25−0.1655 (3)0.5375 (3)−0.3458 (3)0.0378 (7)
H25A−0.12830.5997−0.34430.045*
H25B−0.12460.4974−0.40860.045*
U11U22U33U12U13U23
Au0.02761 (6)0.01936 (6)0.02462 (6)−0.00442 (4)−0.00234 (4)−0.00356 (4)
S10.0360 (4)0.0243 (3)0.0259 (3)−0.0015 (3)−0.0027 (3)−0.0044 (3)
P10.0252 (3)0.0187 (3)0.0247 (3)−0.0053 (3)−0.0015 (2)−0.0049 (2)
O10.0358 (10)0.0254 (10)0.0282 (10)−0.0006 (8)0.0011 (8)−0.0048 (8)
N10.0385 (13)0.0281 (13)0.0303 (13)0.0008 (11)0.0010 (10)−0.0025 (10)
C10.0285 (13)0.0268 (14)0.0289 (14)−0.0059 (11)0.0021 (10)−0.0054 (11)
C20.0455 (18)0.0347 (17)0.0309 (16)0.0037 (14)0.0022 (13)−0.0008 (13)
C30.064 (2)0.058 (2)0.044 (2)−0.011 (2)−0.0136 (17)−0.0071 (17)
C40.064 (2)0.044 (2)0.046 (2)−0.0061 (18)0.0062 (17)0.0104 (16)
C50.0369 (15)0.0297 (15)0.0375 (16)−0.0022 (13)0.0065 (12)−0.0097 (12)
C60.084 (3)0.041 (2)0.062 (3)−0.029 (2)0.030 (2)−0.0193 (18)
C70.0444 (18)0.0478 (19)0.0451 (19)−0.0154 (16)0.0150 (14)−0.0201 (15)
C80.0338 (14)0.0249 (13)0.0318 (14)−0.0083 (11)0.0003 (11)−0.0126 (11)
C90.058 (2)0.0347 (17)0.0484 (19)−0.0249 (16)0.0116 (15)−0.0194 (14)
C100.061 (2)0.0403 (19)0.078 (3)−0.0250 (18)0.0040 (19)−0.0323 (19)
C110.059 (2)0.062 (2)0.080 (3)−0.012 (2)−0.006 (2)−0.052 (2)
C120.094 (3)0.058 (2)0.042 (2)−0.018 (2)0.0045 (19)−0.0297 (18)
C130.072 (2)0.0406 (18)0.0328 (17)−0.0105 (17)−0.0007 (15)−0.0158 (14)
C140.0288 (13)0.0221 (12)0.0286 (13)−0.0088 (11)−0.0002 (10)−0.0043 (10)
C150.0294 (14)0.0299 (15)0.0532 (19)−0.0065 (12)0.0039 (12)−0.0112 (13)
C160.0291 (15)0.0450 (19)0.061 (2)−0.0141 (14)0.0047 (14)−0.0079 (16)
C170.0380 (17)0.0453 (19)0.062 (2)−0.0241 (16)0.0003 (15)−0.0093 (16)
C180.0431 (17)0.0322 (16)0.063 (2)−0.0198 (15)0.0036 (15)−0.0102 (15)
C190.0337 (14)0.0280 (14)0.0434 (17)−0.0125 (12)0.0055 (12)−0.0127 (12)
C200.0252 (12)0.0233 (13)0.0297 (14)−0.0053 (10)−0.0047 (10)−0.0046 (10)
C210.0297 (14)0.0304 (14)0.0325 (15)−0.0060 (12)0.0000 (11)−0.0075 (11)
C220.0282 (15)0.0349 (17)0.057 (2)−0.0050 (13)0.0057 (13)−0.0063 (14)
C230.0271 (14)0.0313 (16)0.056 (2)−0.0050 (12)−0.0045 (13)−0.0038 (14)
C240.0392 (17)0.0387 (18)0.0473 (19)−0.0044 (14)−0.0180 (14)0.0003 (14)
C250.0351 (15)0.0366 (16)0.0298 (15)−0.0056 (13)−0.0067 (12)−0.0012 (12)
Au—S12.3091 (7)C12—C131.524 (5)
Au—P12.2602 (7)C12—H12A0.9800
S1—C11.767 (3)C12—H12B0.9800
P1—C201.842 (3)C13—H13A0.9800
P1—C141.839 (2)C13—H13B0.9800
P1—C81.844 (3)C14—C191.532 (4)
O1—C11.367 (3)C14—C151.535 (4)
O1—C51.452 (3)C14—H140.9900
N1—C11.263 (3)C15—C161.525 (4)
N1—C21.458 (4)C15—H15A0.9800
C2—C41.520 (4)C15—H15B0.9800
C2—C31.524 (5)C16—C171.513 (5)
C2—H20.9900C16—H16A0.9800
C3—H3A0.9700C16—H16B0.9800
C3—H3B0.9700C17—C181.522 (4)
C3—H3C0.9700C17—H17A0.9800
C4—H4A0.9700C17—H17B0.9800
C4—H4B0.9700C18—C191.529 (4)
C4—H4C0.9700C18—H18A0.9800
C5—C71.508 (4)C18—H18B0.9800
C5—C61.500 (5)C19—H19A0.9800
C5—H50.9900C19—H19B0.9800
C6—H6A0.9700C20—C251.536 (4)
C6—H6B0.9700C20—C211.543 (4)
C6—H6C0.9700C20—H200.9900
C7—H7A0.9700C21—C221.531 (4)
C7—H7B0.9700C21—H21A0.9800
C7—H7C0.9700C21—H21B0.9800
C8—C131.519 (4)C22—C231.515 (4)
C8—C91.530 (4)C22—H22A0.9800
C8—H80.9900C22—H22B0.9800
C9—C101.525 (5)C23—C241.512 (5)
C9—H9A0.9800C23—H23A0.9800
C9—H9B0.9800C23—H23B0.9800
C10—C111.514 (6)C24—C251.532 (4)
C10—H10A0.9800C24—H24A0.9800
C10—H10B0.9800C24—H24B0.9800
C11—C121.512 (6)C25—H25A0.9800
C11—H11A0.9800C25—H25B0.9800
C11—H11B0.9800
P1—Au—S1174.94 (2)C8—C13—C12111.3 (3)
C1—S1—Au101.17 (9)C8—C13—H13A109.4
C20—P1—C14108.31 (12)C12—C13—H13A109.4
C20—P1—C8106.97 (12)C8—C13—H13B109.4
C14—P1—C8106.64 (12)C12—C13—H13B109.4
C20—P1—Au116.82 (9)H13A—C13—H13B108.0
C14—P1—Au110.30 (9)C19—C14—C15110.1 (2)
C8—P1—Au107.28 (9)C19—C14—P1109.76 (18)
C1—O1—C5118.2 (2)C15—C14—P1110.57 (18)
C1—N1—C2119.2 (3)C19—C14—H14108.8
N1—C1—O1120.5 (3)C15—C14—H14108.8
N1—C1—S1127.7 (2)P1—C14—H14108.8
O1—C1—S1111.82 (18)C16—C15—C14112.3 (2)
N1—C2—C4109.0 (3)C16—C15—H15A109.1
N1—C2—C3109.0 (3)C14—C15—H15A109.1
C4—C2—C3111.7 (3)C16—C15—H15B109.1
N1—C2—H2109.0C14—C15—H15B109.1
C4—C2—H2109.0H15A—C15—H15B107.9
C3—C2—H2109.0C17—C16—C15111.5 (3)
C2—C3—H3A109.5C17—C16—H16A109.3
C2—C3—H3B109.5C15—C16—H16A109.3
H3A—C3—H3B109.5C17—C16—H16B109.3
C2—C3—H3C109.5C15—C16—H16B109.3
H3A—C3—H3C109.5H16A—C16—H16B108.0
H3B—C3—H3C109.5C16—C17—C18111.4 (3)
C2—C4—H4A109.5C16—C17—H17A109.3
C2—C4—H4B109.5C18—C17—H17A109.3
H4A—C4—H4B109.5C16—C17—H17B109.3
C2—C4—H4C109.5C18—C17—H17B109.3
H4A—C4—H4C109.5H17A—C17—H17B108.0
H4B—C4—H4C109.5C17—C18—C19110.9 (3)
O1—C5—C7105.7 (2)C17—C18—H18A109.5
O1—C5—C6109.4 (3)C19—C18—H18A109.5
C7—C5—C6112.7 (3)C17—C18—H18B109.5
O1—C5—H5109.6C19—C18—H18B109.5
C7—C5—H5109.6H18A—C18—H18B108.0
C6—C5—H5109.6C18—C19—C14112.2 (2)
C5—C6—H6A109.5C18—C19—H19A109.2
C5—C6—H6B109.5C14—C19—H19A109.2
H6A—C6—H6B109.5C18—C19—H19B109.2
C5—C6—H6C109.5C14—C19—H19B109.2
H6A—C6—H6C109.5H19A—C19—H19B107.9
H6B—C6—H6C109.5C25—C20—C21110.5 (2)
C5—C7—H7A109.5C25—C20—P1114.90 (18)
C5—C7—H7B109.5C21—C20—P1111.93 (17)
H7A—C7—H7B109.5C25—C20—H20106.3
C5—C7—H7C109.5C21—C20—H20106.3
H7A—C7—H7C109.5P1—C20—H20106.3
H7B—C7—H7C109.5C22—C21—C20111.2 (2)
C13—C8—C9111.0 (3)C22—C21—H21A109.4
C13—C8—P1116.5 (2)C20—C21—H21A109.4
C9—C8—P1111.1 (2)C22—C21—H21B109.4
C13—C8—H8105.8C20—C21—H21B109.4
C9—C8—H8105.8H21A—C21—H21B108.0
P1—C8—H8105.8C23—C22—C21111.7 (2)
C8—C9—C10110.3 (3)C23—C22—H22A109.3
C8—C9—H9A109.6C21—C22—H22A109.3
C10—C9—H9A109.6C23—C22—H22B109.3
C8—C9—H9B109.6C21—C22—H22B109.3
C10—C9—H9B109.6H22A—C22—H22B107.9
H9A—C9—H9B108.1C24—C23—C22110.5 (3)
C11—C10—C9112.2 (3)C24—C23—H23A109.5
C11—C10—H10A109.2C22—C23—H23A109.5
C9—C10—H10A109.2C24—C23—H23B109.5
C11—C10—H10B109.2C22—C23—H23B109.5
C9—C10—H10B109.2H23A—C23—H23B108.1
H10A—C10—H10B107.9C23—C24—C25110.8 (3)
C12—C11—C10111.6 (3)C23—C24—H24A109.5
C12—C11—H11A109.3C25—C24—H24A109.5
C10—C11—H11A109.3C23—C24—H24B109.5
C12—C11—H11B109.3C25—C24—H24B109.5
C10—C11—H11B109.3H24A—C24—H24B108.1
H11A—C11—H11B108.0C24—C25—C20111.3 (2)
C11—C12—C13110.6 (3)C24—C25—H25A109.4
C11—C12—H12A109.5C20—C25—H25A109.4
C13—C12—H12A109.5C24—C25—H25B109.4
C11—C12—H12B109.5C20—C25—H25B109.4
C13—C12—H12B109.5H25A—C25—H25B108.0
H12A—C12—H12B108.1
C2—N1—C1—O1177.8 (2)Au—P1—C14—C19−62.62 (19)
C2—N1—C1—S1−0.8 (4)C20—P1—C14—C15−172.0 (2)
C5—O1—C1—N1−2.1 (4)C8—P1—C14—C15−57.1 (2)
C5—O1—C1—S1176.71 (19)Au—P1—C14—C1559.0 (2)
Au—S1—C1—N1−173.7 (2)C19—C14—C15—C16−53.6 (3)
Au—S1—C1—O17.64 (19)P1—C14—C15—C16−175.1 (2)
C1—N1—C2—C4146.0 (3)C14—C15—C16—C1755.0 (4)
C1—N1—C2—C3−91.8 (3)C15—C16—C17—C18−55.6 (4)
C1—O1—C5—C7−153.8 (2)C16—C17—C18—C1955.7 (4)
C1—O1—C5—C684.5 (3)C17—C18—C19—C14−55.6 (4)
C20—P1—C8—C1356.3 (3)C15—C14—C19—C1854.1 (3)
C14—P1—C8—C13−59.4 (3)P1—C14—C19—C18176.0 (2)
Au—P1—C8—C13−177.6 (2)C14—P1—C20—C2531.2 (2)
C20—P1—C8—C9−72.0 (2)C8—P1—C20—C25−83.4 (2)
C14—P1—C8—C9172.2 (2)Au—P1—C20—C25156.48 (18)
Au—P1—C8—C954.1 (2)C14—P1—C20—C21−95.9 (2)
C13—C8—C9—C1055.2 (4)C8—P1—C20—C21149.53 (18)
P1—C8—C9—C10−173.5 (2)Au—P1—C20—C2129.4 (2)
C8—C9—C10—C11−54.5 (4)C25—C20—C21—C2253.5 (3)
C9—C10—C11—C1255.0 (4)P1—C20—C21—C22−177.03 (19)
C10—C11—C12—C13−55.3 (5)C20—C21—C22—C23−55.3 (3)
C9—C8—C13—C12−57.0 (4)C21—C22—C23—C2457.4 (4)
P1—C8—C13—C12174.6 (3)C22—C23—C24—C25−58.0 (3)
C11—C12—C13—C856.6 (4)C23—C24—C25—C2057.3 (4)
C20—P1—C14—C1966.4 (2)C21—C20—C25—C24−54.7 (3)
C8—P1—C14—C19−178.80 (19)P1—C20—C25—C24177.5 (2)
Table 1

Selected bond lengths (Å)

Au—S12.3091 (7)
Au—P12.2602 (7)
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Luminescent phosphine gold(I) thiolates: correlation between crystal structure and photoluminescent properties in [R3PAu{SC(OMe)=NC6H4NO2-4}] (R = Et, Cy, Ph) and [(Ph2P-R-PPh2){AuSC(OMe)=NC6H4NO2-4}2] (R = CH2, (CH2)2, (CH2)3, (CH2)4, Fc).

Authors:  Soo Yei Ho; Eddie Chung-Chin Cheng; Edward R T Tiekink; Vivian Wing-Wah Yam
Journal:  Inorg Chem       Date:  2006-10-02       Impact factor: 5.165

  2 in total

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