(2,4,6-Trimethyl­dithio­benzoato)(triphenyl­phosphine)gold(I)

The title compound, [Au(C₁₀H₁₁S₂)(C₁₈H₁₅P)], features an Au^I atom linearly coordinated to a P atom and one S atom of the dithio­benzoate. The S-Au-P bond angle is 177.43 (2)°. In contrast to other reported dithio­benzoate-gold complexes, in which the second S atom is syn with respect to Au, the title compound shows an uncoordinated S atom in an anti conformation.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.027
• wR factor = 0.054
• Data-to-parameter ratio = 35.6

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:      0.431     0.530
            Tmin and Tmax expected:      0.347     0.483
            RR =      1.131
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.12
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.91

Alert level G
ABSTM02_ALERT_3_G  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      0.911
            Tmax scaled      0.483 Tmin scaled      0.393

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

(2,4,6-Trimethyldithiobenzoato)(triphenylphosphine)gold(I)

Crystal data

[Au(C10H11S2)(C18H15P)]	F(000) = 1280
Mr = 654.54	Dx = 1.721 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9809 reflections
a = 8.9954 (10) Å	θ = 2.5–34.3°
b = 20.745 (2) Å	µ = 6.07 mm^−1
c = 13.553 (2) Å	T = 105 K
β = 93.002 (5)°	Fragment, orange
V = 2525.6 (5) Å^3	0.20 × 0.15 × 0.12 mm
Z = 4

Data collection

Nonius KappaCCD (with an Oxford Cryosystems Cryostream coller) diffractometer	8513 reflections with I > 2σ(I)
ω scans with κ offsets	Rint = 0.024
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	θmax = 34.3°, θmin = 2.7°
Tmin = 0.431, Tmax = 0.530	h = −14→14
48287 measured reflections	k = −32→25
10430 independent reflections	l = −21→21

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0096P)^2 + 5.4333P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.027	(Δ/σ)max = 0.001
wR(F^2) = 0.054	Δρmax = 0.84 e Å^−3
S = 0.95	Δρmin = −1.26 e Å^−3
10430 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
293 parameters	Extinction coefficient: 0.00059 (5)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0982 (3)	0.26817 (11)	0.38843 (18)	0.0188 (4)
C2	0.0764 (3)	0.24105 (11)	0.28645 (17)	0.0179 (4)
C3	0.1974 (3)	0.23817 (11)	0.22513 (17)	0.0186 (4)
C4	0.1744 (3)	0.21292 (12)	0.13018 (17)	0.0217 (4)
H4	0.2558	0.2112	0.0883	0.026*
C5	0.0363 (3)	0.19012 (12)	0.09493 (18)	0.0250 (5)
C6	−0.0819 (3)	0.19473 (12)	0.1563 (2)	0.0260 (5)
H6	−0.1774	0.1803	0.1324	0.031*
C7	−0.0655 (3)	0.21972 (12)	0.25150 (19)	0.0230 (5)
C8	−0.1973 (3)	0.22339 (15)	0.3160 (2)	0.0345 (6)
H8A	−0.2887	0.2134	0.2763	0.052*
H8B	−0.2043	0.2669	0.3434	0.052*
H8C	−0.1845	0.1922	0.37	0.052*
C9	0.3504 (3)	0.26111 (13)	0.25984 (19)	0.0252 (5)
H9A	0.4214	0.251	0.2096	0.038*
H9B	0.3811	0.2394	0.3218	0.038*
H9C	0.3483	0.3078	0.2706	0.038*
C10	0.0167 (4)	0.16146 (16)	−0.0073 (2)	0.0389 (7)
H10A	0.0552	0.1173	−0.0065	0.058*
H10B	0.0715	0.1875	−0.0537	0.058*
H10C	−0.0892	0.1611	−0.0282	0.058*
C11	−0.0137 (2)	−0.02173 (12)	0.30954 (16)	0.0181 (4)
C12	−0.1261 (3)	0.01353 (13)	0.25845 (18)	0.0239 (5)
H12	−0.1112	0.0578	0.2439	0.029*
C13	−0.2588 (3)	−0.01630 (15)	0.22914 (18)	0.0277 (5)
H13	−0.3344	0.0074	0.1937	0.033*
C14	−0.2820 (3)	−0.08079 (15)	0.25134 (19)	0.0287 (6)
H14	−0.373	−0.1011	0.2307	0.034*
C15	−0.1719 (3)	−0.11554 (14)	0.30378 (19)	0.0265 (5)
H15	−0.1885	−0.1594	0.3199	0.032*
C16	−0.0374 (3)	−0.08619 (12)	0.33286 (17)	0.0210 (4)
H16	0.038	−0.11	0.3684	0.025*
C17	0.2805 (2)	−0.03747 (11)	0.40625 (16)	0.0163 (4)
C18	0.2961 (3)	−0.03155 (12)	0.50900 (17)	0.0218 (5)
H18	0.2467	0.0022	0.5415	0.026*
C19	0.3842 (3)	−0.07527 (14)	0.56361 (18)	0.0268 (5)
H19	0.3947	−0.0715	0.6335	0.032*
C20	0.4570 (3)	−0.12441 (12)	0.51588 (19)	0.0227 (5)
H20	0.5163	−0.1544	0.5534	0.027*
C21	0.4434 (3)	−0.12987 (11)	0.41408 (18)	0.0205 (4)
H21	0.4945	−0.1632	0.3818	0.025*
C22	0.3551 (3)	−0.08661 (11)	0.35878 (17)	0.0190 (4)
H22	0.3455	−0.0905	0.2889	0.023*
C23	0.2391 (3)	0.02826 (11)	0.21741 (16)	0.0181 (4)
C24	0.1909 (3)	−0.00917 (12)	0.13649 (17)	0.0235 (5)
H24	0.1172	−0.0414	0.1439	0.028*
C25	0.2504 (3)	0.00051 (13)	0.04477 (18)	0.0262 (5)
H25	0.2168	−0.0247	−0.0105	0.031*
C26	0.3595 (3)	0.04743 (13)	0.03442 (18)	0.0247 (5)
H26	0.4	0.0541	−0.0281	0.03*
C27	0.4089 (3)	0.08423 (12)	0.11441 (19)	0.0235 (5)
H27	0.4842	0.1157	0.1071	0.028*
C28	0.3484 (3)	0.07515 (12)	0.20598 (17)	0.0204 (4)
H28	0.3815	0.1009	0.2608	0.024*
Au	0.138235 (10)	0.115470 (4)	0.412664 (6)	0.01810 (3)
P	0.16194 (7)	0.01887 (3)	0.33764 (4)	0.01595 (10)
S2	0.09834 (8)	0.34686 (3)	0.40662 (5)	0.02592 (13)
S1	0.12370 (8)	0.21582 (3)	0.48633 (4)	0.02577 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0207 (10)	0.0153 (9)	0.0206 (10)	0.0038 (8)	0.0019 (8)	0.0018 (8)
C2	0.0203 (10)	0.0151 (9)	0.0180 (10)	0.0017 (8)	−0.0013 (8)	0.0044 (8)
C3	0.0192 (10)	0.0180 (10)	0.0183 (10)	0.0020 (8)	−0.0011 (8)	0.0030 (8)
C4	0.0259 (11)	0.0215 (10)	0.0175 (10)	0.0044 (9)	−0.0013 (9)	0.0029 (8)
C5	0.0345 (13)	0.0196 (11)	0.0199 (11)	0.0027 (10)	−0.0102 (9)	0.0012 (9)
C6	0.0235 (12)	0.0218 (11)	0.0313 (13)	−0.0011 (9)	−0.0106 (10)	0.0065 (10)
C7	0.0204 (11)	0.0216 (11)	0.0266 (12)	−0.0006 (9)	−0.0025 (9)	0.0061 (9)
C8	0.0207 (12)	0.0400 (16)	0.0431 (17)	−0.0004 (11)	0.0040 (11)	0.0080 (13)
C9	0.0198 (11)	0.0313 (13)	0.0243 (12)	−0.0014 (10)	0.0000 (9)	−0.0002 (10)
C10	0.0516 (19)	0.0374 (16)	0.0259 (14)	0.0038 (14)	−0.0159 (13)	−0.0068 (12)
C11	0.0165 (9)	0.0258 (11)	0.0123 (9)	0.0019 (8)	0.0020 (7)	−0.0003 (8)
C12	0.0250 (11)	0.0293 (12)	0.0173 (10)	0.0074 (10)	0.0016 (9)	0.0024 (9)
C13	0.0208 (11)	0.0449 (16)	0.0173 (11)	0.0066 (11)	−0.0006 (9)	0.0009 (10)
C14	0.0202 (11)	0.0466 (16)	0.0193 (11)	−0.0040 (11)	0.0009 (9)	−0.0003 (11)
C15	0.0265 (12)	0.0323 (13)	0.0207 (11)	−0.0066 (11)	0.0004 (9)	0.0024 (10)
C16	0.0216 (11)	0.0261 (11)	0.0153 (10)	−0.0005 (9)	0.0015 (8)	0.0026 (8)
C17	0.0158 (9)	0.0178 (9)	0.0152 (9)	0.0001 (8)	0.0002 (7)	0.0003 (7)
C18	0.0242 (11)	0.0262 (11)	0.0151 (10)	0.0054 (9)	0.0019 (8)	−0.0002 (8)
C19	0.0306 (13)	0.0345 (13)	0.0152 (10)	0.0092 (11)	0.0005 (9)	0.0034 (9)
C20	0.0201 (10)	0.0234 (11)	0.0241 (11)	0.0046 (9)	−0.0023 (9)	0.0050 (9)
C21	0.0197 (10)	0.0171 (10)	0.0249 (11)	0.0010 (8)	0.0029 (9)	−0.0004 (8)
C22	0.0205 (10)	0.0192 (10)	0.0172 (10)	0.0002 (8)	0.0012 (8)	−0.0014 (8)
C23	0.0225 (10)	0.0185 (10)	0.0133 (9)	0.0052 (8)	0.0022 (8)	0.0025 (8)
C24	0.0309 (12)	0.0234 (11)	0.0164 (10)	−0.0010 (10)	0.0042 (9)	−0.0007 (9)
C25	0.0353 (13)	0.0268 (12)	0.0168 (11)	0.0000 (11)	0.0056 (10)	−0.0025 (9)
C26	0.0280 (12)	0.0295 (12)	0.0174 (10)	0.0061 (10)	0.0081 (9)	0.0051 (9)
C27	0.0224 (11)	0.0255 (12)	0.0229 (11)	0.0033 (9)	0.0047 (9)	0.0045 (9)
C28	0.0212 (10)	0.0223 (10)	0.0177 (10)	0.0022 (9)	−0.0002 (8)	0.0024 (8)
Au	0.02475 (4)	0.01548 (4)	0.01414 (4)	0.00363 (3)	0.00162 (3)	0.00069 (3)
P	0.0191 (3)	0.0162 (2)	0.0126 (2)	0.0024 (2)	0.00190 (19)	0.00081 (19)
S2	0.0371 (3)	0.0168 (2)	0.0241 (3)	0.0055 (2)	0.0038 (3)	0.0001 (2)
S1	0.0453 (4)	0.0168 (2)	0.0152 (2)	0.0053 (3)	0.0012 (2)	−0.0002 (2)

Geometric parameters (Å, º)

C1—C2	1.496 (3)	C14—H14	0.95
C1—S2	1.651 (2)	C15—C16	1.393 (3)
C1—S1	1.721 (2)	C15—H15	0.95
C2—C3	1.405 (3)	C16—H16	0.95
C2—C7	1.409 (3)	C17—C22	1.396 (3)
C3—C4	1.395 (3)	C17—C18	1.398 (3)
C3—C9	1.509 (3)	C17—P	1.807 (2)
C4—C5	1.391 (4)	C18—C19	1.392 (3)
C4—H4	0.95	C18—H18	0.95
C5—C6	1.386 (4)	C19—C20	1.389 (4)
C5—C10	1.510 (4)	C19—H19	0.95
C6—C7	1.392 (4)	C20—C21	1.383 (3)
C6—H6	0.95	C20—H20	0.95
C7—C8	1.512 (4)	C21—C22	1.391 (3)
C8—H8A	0.98	C21—H21	0.95
C8—H8B	0.98	C22—H22	0.95
C8—H8C	0.98	C23—C24	1.394 (3)
C9—H9A	0.98	C23—C28	1.397 (3)
C9—H9B	0.98	C23—P	1.815 (2)
C9—H9C	0.98	C24—C25	1.393 (3)
C10—H10A	0.98	C24—H24	0.95
C10—H10B	0.98	C25—C26	1.394 (4)
C10—H10C	0.98	C25—H25	0.95
C11—C16	1.393 (3)	C26—C27	1.380 (4)
C11—C12	1.401 (3)	C26—H26	0.95
C11—P	1.813 (2)	C27—C28	1.394 (3)
C12—C13	1.385 (4)	C27—H27	0.95
C12—H12	0.95	C28—H28	0.95
C13—C14	1.389 (4)	Au—P	2.2623 (6)
C13—H13	0.95	Au—S1	2.3155 (6)
C14—C15	1.390 (4)
C2—C1—S2	120.59 (17)	C14—C15—C16	120.2 (3)
C2—C1—S1	118.75 (16)	C14—C15—H15	119.9
S2—C1—S1	120.66 (15)	C16—C15—H15	119.9
C3—C2—C7	120.2 (2)	C11—C16—C15	119.7 (2)
C3—C2—C1	119.6 (2)	C11—C16—H16	120.1
C7—C2—C1	120.1 (2)	C15—C16—H16	120.1
C4—C3—C2	118.7 (2)	C22—C17—C18	119.9 (2)
C4—C3—C9	119.6 (2)	C22—C17—P	121.35 (17)
C2—C3—C9	121.7 (2)	C18—C17—P	118.79 (17)
C5—C4—C3	122.1 (2)	C19—C18—C17	119.8 (2)
C5—C4—H4	119	C19—C18—H18	120.1
C3—C4—H4	119	C17—C18—H18	120.1
C6—C5—C4	118.0 (2)	C20—C19—C18	120.0 (2)
C6—C5—C10	121.4 (3)	C20—C19—H19	120
C4—C5—C10	120.5 (3)	C18—C19—H19	120
C5—C6—C7	122.3 (2)	C21—C20—C19	120.4 (2)
C5—C6—H6	118.8	C21—C20—H20	119.8
C7—C6—H6	118.8	C19—C20—H20	119.8
C6—C7—C2	118.6 (2)	C20—C21—C22	120.2 (2)
C6—C7—C8	120.5 (2)	C20—C21—H21	119.9
C2—C7—C8	120.9 (2)	C22—C21—H21	119.9
C7—C8—H8A	109.5	C21—C22—C17	119.8 (2)
C7—C8—H8B	109.5	C21—C22—H22	120.1
H8A—C8—H8B	109.5	C17—C22—H22	120.1
C7—C8—H8C	109.5	C24—C23—C28	119.5 (2)
H8A—C8—H8C	109.5	C24—C23—P	121.89 (18)
H8B—C8—H8C	109.5	C28—C23—P	118.60 (18)
C3—C9—H9A	109.5	C23—C24—C25	120.2 (2)
C3—C9—H9B	109.5	C23—C24—H24	119.9
H9A—C9—H9B	109.5	C25—C24—H24	119.9
C3—C9—H9C	109.5	C24—C25—C26	119.7 (2)
H9A—C9—H9C	109.5	C24—C25—H25	120.1
H9B—C9—H9C	109.5	C26—C25—H25	120.1
C5—C10—H10A	109.5	C27—C26—C25	120.4 (2)
C5—C10—H10B	109.5	C27—C26—H26	119.8
H10A—C10—H10B	109.5	C25—C26—H26	119.8
C5—C10—H10C	109.5	C26—C27—C28	120.0 (2)
H10A—C10—H10C	109.5	C26—C27—H27	120
H10B—C10—H10C	109.5	C28—C27—H27	120
C16—C11—C12	119.9 (2)	C27—C28—C23	120.2 (2)
C16—C11—P	122.68 (18)	C27—C28—H28	119.9
C12—C11—P	117.35 (19)	C23—C28—H28	119.9
C13—C12—C11	119.8 (2)	P—Au—S1	177.43 (2)
C13—C12—H12	120.1	C17—P—C11	106.99 (11)
C11—C12—H12	120.1	C17—P—C23	106.74 (10)
C12—C13—C14	120.3 (2)	C11—P—C23	103.38 (11)
C12—C13—H13	119.8	C17—P—Au	114.12 (8)
C14—C13—H13	119.8	C11—P—Au	113.84 (8)
C15—C14—C13	120.0 (2)	C23—P—Au	110.97 (8)
C15—C14—H14	120	C1—S1—Au	104.07 (8)
C13—C14—H14	120
S2—C1—C2—C3	81.1 (3)	C19—C20—C21—C22	−0.9 (4)
S1—C1—C2—C3	−98.7 (2)	C20—C21—C22—C17	0.3 (3)
S2—C1—C2—C7	−97.6 (2)	C18—C17—C22—C21	0.6 (3)
S1—C1—C2—C7	82.5 (3)	P—C17—C22—C21	−178.83 (17)
C7—C2—C3—C4	−1.0 (3)	C28—C23—C24—C25	−0.5 (4)
C1—C2—C3—C4	−179.8 (2)	P—C23—C24—C25	178.5 (2)
C7—C2—C3—C9	179.5 (2)	C23—C24—C25—C26	0.6 (4)
C1—C2—C3—C9	0.7 (3)	C24—C25—C26—C27	0.1 (4)
C2—C3—C4—C5	−0.6 (3)	C25—C26—C27—C28	−0.8 (4)
C9—C3—C4—C5	178.9 (2)	C26—C27—C28—C23	0.9 (4)
C3—C4—C5—C6	1.8 (4)	C24—C23—C28—C27	−0.2 (4)
C3—C4—C5—C10	−178.3 (2)	P—C23—C28—C27	−179.26 (18)
C4—C5—C6—C7	−1.6 (4)	C22—C17—P—C11	79.1 (2)
C10—C5—C6—C7	178.6 (2)	C18—C17—P—C11	−100.3 (2)
C5—C6—C7—C2	0.1 (4)	C22—C17—P—C23	−31.0 (2)
C5—C6—C7—C8	−179.6 (2)	C18—C17—P—C23	149.52 (19)
C3—C2—C7—C6	1.3 (3)	C22—C17—P—Au	−154.00 (16)
C1—C2—C7—C6	−180.0 (2)	C18—C17—P—Au	26.6 (2)
C3—C2—C7—C8	−179.1 (2)	C16—C11—P—C17	−4.6 (2)
C1—C2—C7—C8	−0.3 (3)	C12—C11—P—C17	178.27 (17)
C16—C11—C12—C13	−1.6 (3)	C16—C11—P—C23	107.92 (19)
P—C11—C12—C13	175.63 (18)	C12—C11—P—C23	−69.24 (19)
C11—C12—C13—C14	0.9 (4)	C16—C11—P—Au	−131.59 (17)
C12—C13—C14—C15	0.4 (4)	C12—C11—P—Au	51.24 (19)
C13—C14—C15—C16	−1.0 (4)	C24—C23—P—C17	93.1 (2)
C12—C11—C16—C15	1.0 (3)	C28—C23—P—C17	−87.9 (2)
P—C11—C16—C15	−176.06 (18)	C24—C23—P—C11	−19.6 (2)
C14—C15—C16—C11	0.3 (4)	C28—C23—P—C11	159.41 (18)
C22—C17—C18—C19	−0.9 (4)	C24—C23—P—Au	−142.03 (18)
P—C17—C18—C19	178.6 (2)	C28—C23—P—Au	37.0 (2)
C17—C18—C19—C20	0.3 (4)	C2—C1—S1—Au	5.9 (2)
C18—C19—C20—C21	0.6 (4)	S2—C1—S1—Au	−173.97 (12)