Literature DB >> 21581183

[O-Ethyl N-(4-nitro-phen-yl)thio-carbam-ato-κS](tri-p-tolyl-phosphine-κP)gold(I).

Grant A Broker1, Edward R T Tiekink.   

Abstract

A nearly linear coordination geometry for Au is found in the title compound, [n class="Chemical">Au(C(9)H(9)N(2)O(3)S)(C(21)H(21)P)]. The thio-carbamate ligand is orientated so that the aryl group is in close proximity to the Au atom, consistent with an Au⋯π contact [AuCg = 3.351 (5) Å; Cg is the centroid of the aromatic ring].

Entities:  

Year:  2008        PMID: 21581183      PMCID: PMC2959883          DOI: 10.1107/S1600536808038257

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


Related literature

For related structures and discussion of structural diversity, see: Ho et al. (2006 ▶); Ho & Tiekink (2007 ▶); Kuan et al. (2008 ▶).

Experimental

Crystal data

[Au(C9n class="Species">H9N2O3S)(C21H21P)] M = 726.56 Monoclinic, a = 16.622 (3) Å b = 18.307 (4) Å c = 10.094 (2) Å β = 112.78 (3)° V = 2832.0 (10) Å3 Z = 4 Mo Kα radiation μ = 5.36 mm−1 T = 173 (2) K 0.15 × 0.12 × 0.05 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.739, T max = 1.000 (expected range = 0.565–0.765) 9217 measured reflections 4917 independent reflections 4682 reflections with I > 2σ(I) R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.099 S = 1.06 4917 reflections 346 parameters 2 restraints H-atom parameters constrained Δρmax = 1.37 e Å−3 Δρmin = −2.40 e Å−3 Absolute structure: Flack (1983 ▶), 1980 Friedel pairs Flack parameter: 0.008 (11) Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038257/ng2516sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038257/ng2516Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Au(C9H9N2O3S)(C21H21P)]F000 = 1432
Mr = 726.56Dx = 1.704 Mg m3
Monoclinic, CcMo Kα radiation λ = 0.71070 Å
Hall symbol: C -2ycCell parameters from 6817 reflections
a = 16.622 (3) Åθ = 2.4–30.4º
b = 18.307 (4) ŵ = 5.36 mm1
c = 10.094 (2) ÅT = 173 (2) K
β = 112.78 (3)ºPrism, yellow
V = 2832.0 (10) Å30.15 × 0.12 × 0.05 mm
Z = 4
Rigaku AFC12K/SATURN724 diffractometer4917 independent reflections
Radiation source: fine-focus sealed tube4682 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.059
T = 173(2) Kθmax = 26.5º
ω scansθmin = 2.4º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −20→20
Tmin = 0.739, Tmax = 1.000k = −22→22
9217 measured reflectionsl = −12→10
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048  w = 1/[σ2(Fo2) + (0.0306P)2 + 5.5648P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max < 0.001
S = 1.06Δρmax = 1.37 e Å3
4917 reflectionsΔρmin = −2.40 e Å3
346 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 1980 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.008 (11)
Secondary atom site location: difference Fourier map
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.
xyzUiso*/Ueq
Au0.49939 (4)0.473591 (16)0.74925 (5)0.03122 (11)
S10.59961 (18)0.56583 (13)0.8436 (3)0.0367 (6)
P10.39053 (16)0.39085 (13)0.6519 (3)0.0270 (5)
O10.7581 (5)0.5885 (4)0.8868 (7)0.0355 (16)
O20.5347 (7)0.2127 (6)1.0596 (12)0.055 (3)
O30.5424 (7)0.1666 (5)0.8655 (11)0.074 (3)
N10.7339 (6)0.4654 (4)0.8938 (9)0.032 (2)
N20.5563 (7)0.2152 (6)0.9524 (12)0.049 (3)
C10.6860 (6)0.4052 (5)0.9059 (12)0.030 (2)
C20.6591 (6)0.3981 (6)1.0185 (11)0.031 (2)
H2A0.66930.43711.08510.037*
C30.6179 (7)0.3364 (6)1.0369 (11)0.035 (2)
H3A0.60120.33171.11660.042*
C40.6014 (7)0.2813 (6)0.9367 (12)0.031 (2)
C50.6258 (7)0.2864 (6)0.8200 (12)0.037 (2)
H5A0.61410.24790.75210.044*
C60.6674 (7)0.3490 (6)0.8060 (11)0.035 (2)
H6A0.68390.35400.72620.042*
C70.7041 (7)0.5312 (5)0.8757 (11)0.031 (2)
C80.8498 (7)0.5729 (7)0.9210 (12)0.046 (3)
H8A0.86850.53230.99130.055*
H8B0.88490.61650.96650.055*
C90.8674 (9)0.5524 (8)0.7904 (14)0.052 (3)
H9A0.92980.54230.81880.079*
H9B0.85040.59290.72140.079*
H9C0.83370.50880.74580.079*
C100.2983 (7)0.4272 (5)0.5037 (11)0.029 (2)
C110.2704 (7)0.4981 (6)0.5072 (13)0.041 (3)
H11A0.30010.52740.58950.050*
C120.2010 (8)0.5276 (5)0.3950 (13)0.042 (3)
H12A0.18270.57600.40290.050*
C130.1572 (8)0.4879 (7)0.2704 (12)0.038 (3)
C140.1839 (9)0.4159 (6)0.2679 (12)0.050 (3)
H14A0.15250.38600.18760.060*
C150.2548 (9)0.3868 (6)0.3790 (13)0.053 (3)
H15A0.27420.33890.37050.063*
C160.0830 (10)0.5201 (7)0.1453 (14)0.059 (4)
H16A0.08250.49910.05560.088*
H16B0.09020.57310.14410.088*
H16C0.02770.50880.15450.088*
C170.3478 (6)0.3540 (5)0.7770 (10)0.028 (2)
C180.2710 (7)0.3149 (6)0.7351 (11)0.038 (2)
H18A0.23560.31050.63570.045*
C190.2448 (7)0.2826 (6)0.8332 (12)0.038 (2)
H19A0.19130.25650.80080.045*
C200.2947 (8)0.2870 (6)0.9794 (11)0.039 (3)
C210.3698 (7)0.3280 (6)1.0242 (11)0.036 (2)
H21A0.40370.33291.12410.043*
C220.3968 (6)0.3624 (6)0.9264 (11)0.037 (2)
H22A0.44810.39150.95930.044*
C230.2631 (9)0.2489 (7)1.0866 (13)0.054 (3)
H23A0.31210.24381.17960.081*
H23B0.24020.20041.05000.081*
H23C0.21700.27821.09850.081*
C240.4231 (6)0.3135 (5)0.5721 (10)0.025 (2)
C250.4745 (7)0.3277 (6)0.4931 (11)0.037 (2)
H25A0.49530.37580.49000.044*
C260.4948 (7)0.2714 (6)0.4193 (11)0.036 (2)
H26A0.52850.28180.36420.043*
C270.4667 (10)0.1993 (7)0.4240 (15)0.041 (3)
C280.4187 (8)0.1867 (7)0.5063 (14)0.044 (3)
H28A0.40020.13830.51290.053*
C290.3960 (7)0.2420 (6)0.5805 (12)0.036 (2)
H29A0.36260.23130.63600.043*
C300.4884 (10)0.1410 (7)0.3408 (14)0.058 (3)
H30A0.45590.09650.34200.087*
H30B0.55110.13080.38420.087*
H30C0.47250.15720.24130.087*
U11U22U33U12U13U23
Au0.03049 (18)0.03164 (17)0.03174 (19)−0.0017 (2)0.01226 (14)0.0001 (2)
S10.0368 (14)0.0270 (11)0.0499 (16)−0.0055 (11)0.0207 (13)−0.0056 (11)
P10.0262 (13)0.0295 (12)0.0239 (13)−0.0029 (10)0.0083 (11)0.0002 (10)
O10.036 (4)0.036 (4)0.035 (4)−0.005 (3)0.015 (3)0.000 (3)
O20.059 (7)0.052 (6)0.061 (7)−0.001 (5)0.032 (6)0.022 (5)
O30.091 (8)0.051 (5)0.070 (7)−0.019 (6)0.021 (6)0.001 (5)
N10.030 (5)0.031 (4)0.030 (5)−0.007 (4)0.006 (4)−0.007 (4)
N20.037 (6)0.047 (6)0.042 (7)−0.006 (5)−0.007 (5)0.008 (5)
C10.029 (5)0.028 (5)0.032 (6)0.007 (4)0.011 (5)0.004 (4)
C20.029 (6)0.033 (5)0.030 (6)0.003 (4)0.012 (5)0.003 (4)
C30.033 (6)0.048 (6)0.022 (5)0.009 (5)0.008 (5)0.010 (5)
C40.021 (5)0.035 (6)0.035 (6)0.001 (5)0.009 (5)0.004 (5)
C50.033 (6)0.032 (5)0.047 (7)−0.010 (5)0.018 (5)−0.013 (5)
C60.044 (6)0.040 (6)0.027 (6)0.003 (5)0.019 (5)−0.002 (5)
C70.033 (6)0.035 (5)0.025 (5)−0.018 (4)0.012 (5)−0.001 (4)
C80.036 (6)0.060 (7)0.036 (6)−0.020 (6)0.008 (5)−0.002 (5)
C90.049 (8)0.056 (8)0.049 (8)−0.011 (7)0.015 (7)−0.002 (7)
C100.034 (6)0.027 (5)0.029 (6)0.000 (4)0.017 (5)0.002 (4)
C110.042 (7)0.030 (5)0.046 (7)0.002 (5)0.010 (6)−0.002 (5)
C120.049 (7)0.024 (5)0.042 (7)0.003 (5)0.006 (6)−0.003 (4)
C130.036 (6)0.046 (6)0.031 (6)0.007 (5)0.013 (5)0.011 (5)
C140.068 (9)0.041 (6)0.026 (6)0.016 (6)0.001 (6)−0.006 (5)
C150.067 (9)0.028 (5)0.049 (7)0.007 (6)0.008 (7)−0.008 (5)
C160.077 (10)0.050 (7)0.046 (8)0.028 (7)0.021 (8)0.009 (6)
C170.030 (5)0.039 (5)0.021 (5)0.007 (4)0.016 (5)0.010 (4)
C180.033 (6)0.052 (6)0.025 (5)−0.008 (5)0.009 (5)−0.001 (5)
C190.031 (6)0.043 (6)0.038 (6)−0.006 (5)0.012 (5)0.005 (5)
C200.052 (7)0.041 (6)0.024 (6)−0.003 (5)0.014 (5)−0.001 (5)
C210.040 (6)0.036 (5)0.032 (6)0.009 (5)0.013 (5)−0.004 (4)
C220.024 (5)0.051 (6)0.033 (6)0.002 (5)0.009 (5)0.000 (5)
C230.068 (9)0.059 (8)0.043 (7)0.006 (7)0.032 (7)0.014 (6)
C240.019 (5)0.029 (5)0.024 (5)−0.005 (4)0.004 (4)0.005 (4)
C250.038 (6)0.036 (5)0.044 (6)−0.006 (5)0.025 (6)0.006 (5)
C260.044 (6)0.039 (6)0.036 (6)0.005 (5)0.029 (5)0.002 (5)
C270.047 (8)0.035 (6)0.039 (8)0.013 (6)0.015 (7)0.008 (5)
C280.049 (8)0.048 (7)0.044 (8)0.005 (6)0.025 (7)0.002 (6)
C290.036 (6)0.036 (6)0.037 (6)−0.001 (5)0.015 (5)0.005 (5)
C300.080 (10)0.049 (7)0.051 (8)0.010 (7)0.032 (8)−0.003 (6)
Au—P12.271 (3)C13—C161.502 (17)
Au—S12.303 (3)C14—C151.380 (17)
S1—C71.757 (11)C14—H14A0.9500
P1—C171.801 (9)C15—H15A0.9500
P1—C101.804 (11)C16—H16A0.9800
P1—C241.813 (10)C16—H16B0.9800
O1—C71.358 (11)C16—H16C0.9800
O1—C81.454 (13)C17—C181.380 (14)
O2—N21.266 (15)C17—C221.417 (14)
O3—N21.207 (14)C18—C191.361 (13)
N1—C71.287 (12)C18—H18A0.9500
N1—C11.392 (12)C19—C201.388 (15)
N2—C41.464 (15)C19—H19A0.9500
C1—C21.380 (13)C20—C211.375 (16)
C1—C61.389 (14)C20—C231.540 (14)
C2—C31.371 (15)C21—C221.384 (14)
C2—H2A0.9500C21—H21A0.9500
C3—C41.378 (16)C22—H22A0.9500
C3—H3A0.9500C23—H23A0.9800
C4—C51.390 (14)C23—H23B0.9800
C5—C61.374 (14)C23—H23C0.9800
C5—H5A0.9500C24—C291.397 (13)
C6—H6A0.9500C24—C251.400 (12)
C8—C91.505 (16)C25—C261.388 (14)
C8—H8A0.9900C25—H25A0.9500
C8—H8B0.9900C26—C271.407 (17)
C9—H9A0.9800C26—H26A0.9500
C9—H9B0.9800C27—C281.376 (18)
C9—H9C0.9800C27—C301.487 (17)
C10—C111.384 (14)C28—C291.396 (16)
C10—C151.396 (15)C28—H28A0.9500
C11—C121.376 (16)C29—H29A0.9500
C11—H11A0.9500C30—H30A0.9800
C12—C131.389 (16)C30—H30B0.9800
C12—H12A0.9500C30—H30C0.9800
C13—C141.395 (15)
P1—Au—S1174.54 (10)C15—C14—H14A119.1
C7—S1—Au108.4 (3)C13—C14—H14A119.1
C17—P1—C10106.3 (5)C14—C15—C10120.6 (10)
C17—P1—C24106.6 (4)C14—C15—H15A119.7
C10—P1—C24102.9 (4)C10—C15—H15A119.7
C17—P1—Au114.2 (4)C13—C16—H16A109.5
C10—P1—Au113.1 (3)C13—C16—H16B109.5
C24—P1—Au112.8 (3)H16A—C16—H16B109.5
C7—O1—C8117.8 (8)C13—C16—H16C109.5
C7—N1—C1123.4 (9)H16A—C16—H16C109.5
O3—N2—O2123.8 (11)H16B—C16—H16C109.5
O3—N2—C4119.5 (11)C18—C17—C22117.6 (8)
O2—N2—C4116.7 (11)C18—C17—P1123.3 (8)
C2—C1—C6118.4 (9)C22—C17—P1119.0 (8)
C2—C1—N1121.7 (10)C19—C18—C17121.4 (10)
C6—C1—N1119.8 (9)C19—C18—H18A119.3
C3—C2—C1121.9 (10)C17—C18—H18A119.3
C3—C2—H2A119.1C18—C19—C20121.4 (10)
C1—C2—H2A119.1C18—C19—H19A119.3
C2—C3—C4118.1 (9)C20—C19—H19A119.3
C2—C3—H3A120.9C21—C20—C19118.3 (10)
C4—C3—H3A120.9C21—C20—C23122.0 (10)
C3—C4—C5122.1 (10)C19—C20—C23119.7 (11)
C3—C4—N2119.4 (10)C20—C21—C22121.2 (10)
C5—C4—N2118.5 (10)C20—C21—H21A119.4
C6—C5—C4117.9 (10)C22—C21—H21A119.4
C6—C5—H5A121.0C21—C22—C17119.9 (10)
C4—C5—H5A121.0C21—C22—H22A120.0
C5—C6—C1121.5 (9)C17—C22—H22A120.0
C5—C6—H6A119.3C20—C23—H23A109.5
C1—C6—H6A119.3C20—C23—H23B109.5
N1—C7—O1120.3 (10)H23A—C23—H23B109.5
N1—C7—S1131.5 (8)C20—C23—H23C109.5
O1—C7—S1108.1 (7)H23A—C23—H23C109.5
O1—C8—C9112.5 (9)H23B—C23—H23C109.5
O1—C8—H8A109.1C29—C24—C25119.5 (9)
C9—C8—H8A109.1C29—C24—P1123.0 (8)
O1—C8—H8B109.1C25—C24—P1117.4 (7)
C9—C8—H8B109.1C26—C25—C24119.7 (9)
H8A—C8—H8B107.8C26—C25—H25A120.1
C8—C9—H9A109.5C24—C25—H25A120.1
C8—C9—H9B109.5C25—C26—C27121.7 (9)
H9A—C9—H9B109.5C25—C26—H26A119.2
C8—C9—H9C109.5C27—C26—H26A119.2
H9A—C9—H9C109.5C28—C27—C26117.1 (12)
H9B—C9—H9C109.5C28—C27—C30123.1 (13)
C11—C10—C15117.3 (10)C26—C27—C30119.9 (11)
C11—C10—P1120.7 (8)C27—C28—C29122.9 (12)
C15—C10—P1122.0 (8)C27—C28—H28A118.5
C12—C11—C10121.9 (10)C29—C28—H28A118.5
C12—C11—H11A119.0C24—C29—C28119.0 (10)
C10—C11—H11A119.0C24—C29—H29A120.5
C11—C12—C13121.3 (10)C28—C29—H29A120.5
C11—C12—H12A119.3C27—C30—H30A109.5
C13—C12—H12A119.3C27—C30—H30B109.5
C12—C13—C14116.8 (10)H30A—C30—H30B109.5
C12—C13—C16121.9 (11)C27—C30—H30C109.5
C14—C13—C16121.3 (12)H30A—C30—H30C109.5
C15—C14—C13121.9 (11)H30B—C30—H30C109.5
P1—Au—S1—C7−170.4 (10)C12—C13—C14—C15−4.9 (19)
S1—Au—P1—C17−86.1 (11)C16—C13—C14—C15176.6 (12)
S1—Au—P1—C1035.6 (12)C13—C14—C15—C105(2)
S1—Au—P1—C24151.9 (10)C11—C10—C15—C14−3.5 (18)
C7—N1—C1—C2−63.7 (14)P1—C10—C15—C14179.4 (10)
C7—N1—C1—C6119.0 (11)C10—P1—C17—C1841.1 (10)
C6—C1—C2—C32.6 (15)C24—P1—C17—C18−68.2 (9)
N1—C1—C2—C3−174.8 (9)Au—P1—C17—C18166.5 (8)
C1—C2—C3—C4−1.9 (15)C10—P1—C17—C22−141.8 (8)
C2—C3—C4—C50.6 (16)C24—P1—C17—C22108.9 (9)
C2—C3—C4—N2−179.0 (9)Au—P1—C17—C22−16.5 (9)
O3—N2—C4—C3−179.4 (11)C22—C17—C18—C19−3.0 (15)
O2—N2—C4—C30.1 (16)P1—C17—C18—C19174.2 (9)
O3—N2—C4—C50.9 (16)C17—C18—C19—C20−0.6 (17)
O2—N2—C4—C5−179.6 (10)C18—C19—C20—C213.2 (16)
C3—C4—C5—C6−0.2 (16)C18—C19—C20—C23−179.4 (10)
N2—C4—C5—C6179.5 (10)C19—C20—C21—C22−2.0 (16)
C4—C5—C6—C11.0 (17)C23—C20—C21—C22−179.4 (10)
C2—C1—C6—C5−2.1 (16)C20—C21—C22—C17−1.5 (15)
N1—C1—C6—C5175.3 (10)C18—C17—C22—C214.0 (15)
C1—N1—C7—O1169.9 (9)P1—C17—C22—C21−173.2 (8)
C1—N1—C7—S1−7.1 (16)C17—P1—C24—C2915.8 (10)
C8—O1—C7—N1−0.7 (13)C10—P1—C24—C29−95.9 (9)
C8—O1—C7—S1176.9 (7)Au—P1—C24—C29142.0 (8)
Au—S1—C7—N1−21.9 (11)C17—P1—C24—C25−167.3 (8)
Au—S1—C7—O1160.9 (5)C10—P1—C24—C2581.1 (9)
C7—O1—C8—C983.3 (12)Au—P1—C24—C25−41.1 (9)
C17—P1—C10—C1187.5 (9)C29—C24—C25—C262.7 (16)
C24—P1—C10—C11−160.6 (8)P1—C24—C25—C26−174.4 (9)
Au—P1—C10—C11−38.6 (9)C24—C25—C26—C27−1.4 (18)
C17—P1—C10—C15−95.5 (10)C25—C26—C27—C28−1(2)
C24—P1—C10—C1516.3 (10)C25—C26—C27—C30178.7 (12)
Au—P1—C10—C15138.4 (9)C26—C27—C28—C291(2)
C15—C10—C11—C122.0 (17)C30—C27—C28—C29−177.9 (13)
P1—C10—C11—C12179.2 (9)C25—C24—C29—C28−1.9 (16)
C10—C11—C12—C13−2.1 (18)P1—C24—C29—C28175.0 (9)
C11—C12—C13—C143.3 (18)C27—C28—C29—C24−0.3 (19)
C11—C12—C13—C16−178.2 (11)
  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
  1 in total

1.  New monoclinic form of {O-Ethyl N-(4-nitro-phen-yl)thio-carbamato-κS}(tri-4-tolyl-phosphane-κP)gold(I): crystal structure and Hirshfeld surface analysis.

Authors:  Fong Sheen Kuan; Mukesh M Jotani; Edward R T Tiekink
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-09-15
  1 in total

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