A second polymorph of (2-thiazolidinethionato)­(triphenyl­phosphine)gold(I)

The title compound, [Au(C₃H₄NS₂)(C₁₈H₁₅P)], contains a thiazolidinethione ligand coordinated to an Au^I atom through the S atom. A triphenyl­phosphine ligand completes the linear coordination geometry around the Au atom. The compound contains two mol­ecules in the asymmetric unit and is a polymorphic form of a previously reported structure [Grant, Forward & Fackler Jr (1996). Z. Kristallogr. 211, 483–484]. The composite mol­ecules in the two forms exhibit nearly identical bond distances and angles.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.035
• wR factor = 0.088
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S2     -   C1      ..       9.46 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S2     -   C2      ..       7.86 su

Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED.

(2-thiolidinethionato)(triphenylphosphine)gold(I)

Crystal data

[Au(C3H4NS2)(C18H15P)]	Z = 2
Mr = 577.43	F(000) = 556
Triclinic, P1	Dx = 1.921 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8944 (13) Å	Cell parameters from 4034 reflections
b = 10.6804 (16) Å	θ = 2.5–26.7°
c = 11.4533 (17) Å	µ = 7.66 mm^−1
α = 86.763 (3)°	T = 100 K
β = 87.498 (2)°	Block, colourless
γ = 66.828 (3)°	0.14 × 0.10 × 0.07 mm
V = 998.4 (3) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	4108 independent reflections
Radiation source: fine-focus sealed tube	3789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scans	θmax = 26.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −7→11
Tmin = 0.319, Tmax = 0.585	k = −13→13
5909 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 4.1532P] where P = (Fo^2 + 2Fc^2)/3
4108 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 2.39 e Å^−3
0 restraints	Δρmin = −1.53 e Å^−3

Special details

Experimental. Spectroscopic analysis: IR (KBr, ν_max/cm^-1): 3068, 3049, 2962, 1686, 1576, 1547, 1479, 1435, 1296, 1261, 1099, 1026, 997, 957, 910, 802, 746, 692; ¹H NMR (CD₂Cl₂): δ 7.53 (m, 15H), 4.22 (m, 2H), 3.81 (m, 2H); ¹³C NMR (CD₂Cl₂): δ 169.0, 134.9 (d, J = 14.1 Hz), 132.4, 130.5, 129.8 (d, J = 11.5 Hz), 68.6, 66.2; ³¹P NMR (CD₂Cl₂): δ 37.4; FAB–MS: m/z = 578 (26%) [M]⁺, 459 (82%) [AuPPh₃].

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.

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

	x	y	z	Uiso*/Ueq
Au1	0.28573 (3)	0.38759 (2)	0.078327 (18)	0.01808 (9)
P1	0.37744 (18)	0.43714 (15)	0.24274 (13)	0.0180 (3)
S1	0.2057 (2)	0.33384 (16)	−0.09419 (14)	0.0246 (3)
S2	0.2837 (3)	0.0811 (2)	0.0644 (2)	0.0526 (5)
N1	0.2583 (7)	0.0844 (6)	−0.1583 (5)	0.0294 (12)
C1	0.2497 (7)	0.1602 (6)	−0.0739 (5)	0.0227 (12)
C3	0.3002 (11)	−0.0564 (8)	−0.1172 (7)	0.0404 (18)
H3	0.4120	−0.1133	−0.1452	0.048*
H4	0.2234	−0.0913	−0.1496	0.048*
C2	0.2918 (11)	−0.0672 (10)	0.0142 (8)	0.054 (2)
H2	0.3896	−0.1440	0.0441	0.065*
H1	0.1933	−0.0833	0.0408	0.065*
C10	0.3140 (7)	0.6174 (6)	0.2676 (5)	0.0195 (11)
C15	0.1496 (7)	0.7036 (6)	0.2556 (6)	0.0239 (13)
H15	0.0737	0.6689	0.2303	0.029*
C14	0.0972 (8)	0.8400 (7)	0.2807 (6)	0.0270 (14)
H14	−0.0152	0.8980	0.2745	0.032*
C13	0.2073 (8)	0.8921 (6)	0.3146 (6)	0.0268 (13)
H13	0.1704	0.9852	0.3329	0.032*
C12	0.3729 (8)	0.8074 (7)	0.3219 (6)	0.0299 (14)
H12	0.4494	0.8436	0.3429	0.036*
C11	0.4258 (7)	0.6707 (6)	0.2986 (6)	0.0248 (13)
H11	0.5386	0.6133	0.3036	0.030*
C16	0.3130 (7)	0.3641 (6)	0.3728 (5)	0.0189 (11)
C21	0.2389 (7)	0.4411 (7)	0.4688 (5)	0.0237 (13)
H21	0.2162	0.5358	0.4666	0.028*
C20	0.1979 (7)	0.3787 (7)	0.5683 (5)	0.0253 (13)
H20	0.1471	0.4311	0.6340	0.030*
C19	0.2311 (7)	0.2409 (7)	0.5715 (6)	0.0267 (14)
H19	0.2040	0.1989	0.6399	0.032*
C18	0.3037 (8)	0.1632 (7)	0.4759 (6)	0.0273 (14)
H18	0.3262	0.0685	0.4785	0.033*
C17	0.3431 (8)	0.2253 (7)	0.3763 (6)	0.0258 (13)
H17	0.3910	0.1731	0.3099	0.031*
C4	0.5993 (7)	0.3671 (6)	0.2478 (6)	0.0219 (12)
C9	0.6864 (8)	0.3740 (6)	0.1449 (6)	0.0243 (13)
H9	0.6295	0.4100	0.0744	0.029*
C8	0.8553 (8)	0.3286 (7)	0.1449 (7)	0.0315 (15)
H8	0.9139	0.3346	0.0749	0.038*
C7	0.9384 (8)	0.2748 (7)	0.2468 (7)	0.0329 (16)
H7	1.0542	0.2436	0.2467	0.039*
C6	0.8538 (8)	0.2658 (7)	0.3493 (7)	0.0334 (16)
H6	0.9118	0.2276	0.4189	0.040*
C5	0.6829 (8)	0.3132 (7)	0.3502 (6)	0.0265 (13)
H5	0.6245	0.3084	0.4207	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.02163 (13)	0.02243 (13)	0.01275 (13)	−0.01159 (9)	−0.00093 (8)	0.00116 (8)
P1	0.0185 (7)	0.0214 (7)	0.0154 (7)	−0.0096 (6)	−0.0001 (5)	0.0014 (6)
S1	0.0354 (8)	0.0226 (7)	0.0189 (7)	−0.0146 (7)	−0.0076 (6)	0.0037 (6)
S2	0.0656 (14)	0.0467 (12)	0.0424 (12)	−0.0185 (11)	0.0060 (10)	−0.0095 (10)
N1	0.045 (3)	0.025 (3)	0.024 (3)	−0.019 (3)	−0.003 (2)	−0.002 (2)
C1	0.019 (3)	0.026 (3)	0.022 (3)	−0.008 (2)	0.001 (2)	0.006 (2)
C3	0.059 (5)	0.030 (4)	0.034 (4)	−0.020 (4)	−0.011 (4)	0.009 (3)
C2	0.049 (5)	0.069 (6)	0.039 (5)	−0.021 (5)	−0.002 (4)	0.024 (4)
C10	0.021 (3)	0.023 (3)	0.014 (3)	−0.009 (2)	−0.002 (2)	0.003 (2)
C15	0.020 (3)	0.024 (3)	0.027 (3)	−0.009 (2)	−0.004 (2)	0.007 (2)
C14	0.020 (3)	0.027 (3)	0.031 (4)	−0.006 (3)	−0.001 (3)	0.006 (3)
C13	0.028 (3)	0.021 (3)	0.027 (3)	−0.005 (3)	−0.001 (3)	0.000 (3)
C12	0.029 (3)	0.026 (3)	0.036 (4)	−0.010 (3)	−0.010 (3)	−0.004 (3)
C11	0.020 (3)	0.027 (3)	0.026 (3)	−0.007 (3)	−0.006 (2)	0.000 (3)
C16	0.019 (3)	0.027 (3)	0.013 (3)	−0.012 (2)	−0.003 (2)	0.001 (2)
C21	0.019 (3)	0.030 (3)	0.023 (3)	−0.010 (3)	−0.002 (2)	−0.001 (3)
C20	0.017 (3)	0.035 (4)	0.019 (3)	−0.007 (3)	0.003 (2)	0.003 (3)
C19	0.022 (3)	0.041 (4)	0.019 (3)	−0.017 (3)	−0.002 (2)	0.013 (3)
C18	0.031 (3)	0.032 (3)	0.023 (3)	−0.017 (3)	−0.003 (3)	0.009 (3)
C17	0.030 (3)	0.029 (3)	0.023 (3)	−0.015 (3)	−0.002 (2)	−0.001 (3)
C4	0.019 (3)	0.020 (3)	0.027 (3)	−0.007 (2)	0.001 (2)	−0.005 (2)
C9	0.027 (3)	0.019 (3)	0.026 (3)	−0.009 (3)	0.001 (2)	0.007 (2)
C8	0.021 (3)	0.025 (3)	0.046 (4)	−0.009 (3)	0.001 (3)	0.008 (3)
C7	0.017 (3)	0.020 (3)	0.061 (5)	−0.007 (3)	0.000 (3)	0.000 (3)
C6	0.028 (3)	0.029 (3)	0.038 (4)	−0.004 (3)	−0.012 (3)	−0.003 (3)
C5	0.028 (3)	0.028 (3)	0.021 (3)	−0.008 (3)	−0.001 (2)	−0.006 (3)

Geometric parameters (Å, º)

Au1—P1	2.2535 (15)	C12—H12	0.9500
Au1—S1	2.3051 (15)	C11—H11	0.9500
P1—C10	1.817 (6)	C16—C21	1.390 (8)
P1—C4	1.816 (6)	C16—C17	1.397 (9)
P1—C16	1.817 (6)	C21—C20	1.394 (9)
S1—C1	1.741 (6)	C21—H21	0.9500
S2—C2	1.689 (11)	C20—C19	1.381 (10)
S2—C1	1.733 (7)	C20—H20	0.9500
N1—C1	1.277 (8)	C19—C18	1.387 (9)
N1—C3	1.455 (9)	C19—H19	0.9500
C3—C2	1.503 (11)	C18—C17	1.388 (9)
C3—H3	0.9900	C18—H18	0.9500
C3—H4	0.9900	C17—H17	0.9500
C2—H2	0.9900	C4—C5	1.387 (9)
C2—H1	0.9900	C4—C9	1.397 (8)
C10—C11	1.392 (8)	C9—C8	1.385 (9)
C10—C15	1.396 (8)	C9—H9	0.9500
C15—C14	1.387 (9)	C8—C7	1.380 (10)
C15—H15	0.9500	C8—H8	0.9500
C14—C13	1.380 (9)	C7—C6	1.385 (11)
C14—H14	0.9500	C7—H7	0.9500
C13—C12	1.396 (9)	C6—C5	1.401 (9)
C13—H13	0.9500	C6—H6	0.9500
C12—C11	1.384 (9)	C5—H5	0.9500
P1—Au1—S1	176.96 (5)	C12—C11—C10	120.1 (6)
C10—P1—C4	105.1 (3)	C12—C11—H11	120.0
C10—P1—C16	106.0 (3)	C10—C11—H11	120.0
C4—P1—C16	104.7 (3)	C21—C16—C17	119.6 (6)
C10—P1—Au1	115.7 (2)	C21—C16—P1	122.1 (5)
C4—P1—Au1	112.7 (2)	C17—C16—P1	118.3 (5)
C16—P1—Au1	111.82 (19)	C16—C21—C20	119.8 (6)
C1—S1—Au1	103.2 (2)	C16—C21—H21	120.1
C2—S2—C1	92.4 (4)	C20—C21—H21	120.1
C1—N1—C3	111.3 (6)	C19—C20—C21	120.1 (6)
N1—C1—S2	116.2 (5)	C19—C20—H20	120.0
N1—C1—S1	122.7 (5)	C21—C20—H20	120.0
S2—C1—S1	121.0 (4)	C20—C19—C18	120.7 (6)
N1—C3—C2	110.7 (7)	C20—C19—H19	119.7
N1—C3—H3	109.5	C18—C19—H19	119.7
C2—C3—H3	109.5	C19—C18—C17	119.3 (6)
N1—C3—H4	109.5	C19—C18—H18	120.3
C2—C3—H4	109.5	C17—C18—H18	120.3
H3—C3—H4	108.1	C18—C17—C16	120.5 (6)
C3—C2—S2	107.7 (6)	C18—C17—H17	119.7
C3—C2—H2	110.2	C16—C17—H17	119.7
S2—C2—H2	110.2	C5—C4—C9	119.6 (6)
C3—C2—H1	110.2	C5—C4—P1	122.5 (5)
S2—C2—H1	110.2	C9—C4—P1	117.8 (5)
H2—C2—H1	108.5	C8—C9—C4	120.4 (6)
C11—C10—C15	119.6 (6)	C8—C9—H9	119.8
C11—C10—P1	121.3 (5)	C4—C9—H9	119.8
C15—C10—P1	119.0 (5)	C7—C8—C9	119.9 (6)
C14—C15—C10	119.8 (6)	C7—C8—H8	120.1
C14—C15—H15	120.1	C9—C8—H8	120.1
C10—C15—H15	120.1	C8—C7—C6	120.4 (6)
C13—C14—C15	120.5 (6)	C8—C7—H7	119.8
C13—C14—H14	119.8	C6—C7—H7	119.8
C15—C14—H14	119.8	C7—C6—C5	120.0 (6)
C14—C13—C12	119.8 (6)	C7—C6—H6	120.0
C14—C13—H13	120.1	C5—C6—H6	120.0
C12—C13—H13	120.1	C4—C5—C6	119.7 (6)
C11—C12—C13	120.1 (6)	C4—C5—H5	120.2
C11—C12—H12	119.9	C6—C5—H5	120.2
C13—C12—H12	119.9
C3—N1—C1—S2	−1.5 (8)	C10—P1—C16—C17	178.5 (5)
C3—N1—C1—S1	178.8 (5)	C4—P1—C16—C17	−70.7 (5)
C2—S2—C1—N1	−6.3 (6)	Au1—P1—C16—C17	51.6 (5)
C2—S2—C1—S1	173.4 (5)	C17—C16—C21—C20	1.1 (9)
Au1—S1—C1—N1	−163.6 (5)	P1—C16—C21—C20	−177.4 (4)
Au1—S1—C1—S2	16.7 (4)	C16—C21—C20—C19	0.1 (9)
C1—N1—C3—C2	10.1 (9)	C21—C20—C19—C18	−0.7 (9)
N1—C3—C2—S2	−14.1 (9)	C20—C19—C18—C17	0.1 (9)
C1—S2—C2—C3	11.1 (6)	C19—C18—C17—C16	1.2 (9)
C4—P1—C10—C11	−7.4 (6)	C21—C16—C17—C18	−1.7 (9)
C16—P1—C10—C11	103.1 (5)	P1—C16—C17—C18	176.8 (5)
Au1—P1—C10—C11	−132.4 (5)	C10—P1—C4—C5	91.4 (6)
C4—P1—C10—C15	172.7 (5)	C16—P1—C4—C5	−20.0 (6)
C16—P1—C10—C15	−76.8 (5)	Au1—P1—C4—C5	−141.7 (5)
Au1—P1—C10—C15	47.7 (5)	C10—P1—C4—C9	−85.8 (5)
C11—C10—C15—C14	−3.5 (9)	C16—P1—C4—C9	162.8 (5)
P1—C10—C15—C14	176.3 (5)	Au1—P1—C4—C9	41.0 (5)
C10—C15—C14—C13	1.7 (10)	C5—C4—C9—C8	−0.6 (9)
C15—C14—C13—C12	1.0 (10)	P1—C4—C9—C8	176.7 (5)
C14—C13—C12—C11	−1.9 (11)	C4—C9—C8—C7	0.8 (10)
C13—C12—C11—C10	0.0 (10)	C9—C8—C7—C6	0.0 (10)
C15—C10—C11—C12	2.7 (10)	C8—C7—C6—C5	−0.8 (10)
P1—C10—C11—C12	−177.2 (5)	C9—C4—C5—C6	−0.2 (9)
C10—P1—C16—C21	−3.1 (6)	P1—C4—C5—C6	−177.4 (5)
C4—P1—C16—C21	107.7 (5)	C7—C6—C5—C4	0.9 (10)
Au1—P1—C16—C21	−129.9 (4)