4,5-Bis­(ferrocenyl­methyl­thio)-1,3-di­thiol-2-one

In the compound 4,5-bis­(ferrocenyl­methyl­thio)-1,3-di­thiol-2-one, [Fe₂(C₅H₅)₂(C₁₅H₁₂OS₄)], the values of the geometric parameters of the ferrocene and 1,3-di­thiol-2-one (dmio) moieties are within normal ranges. The dmio group is essentially planar. There are no short S...S contacts.

S1. Comment

Examination of the title structure, (I), with PLATON (Spek, 1998) showed that there were no solvent-accessible voids in the crystal lattice.

S2. Experimental

The title compound was prepared from (chloromethyl)ferrocene and [NEt₄]₂[Zn(dmio)₂] and was recrystallized from dichloromethane/petroleum ether (333–353 K) producing orange crystals (m.p. 97–99°C).

S3. Refinement

The title compound crystallized in the monoclinic system; space group P2₁/n from the systematic absences. H atoms were treated as riding atoms with C—H distances in the range 0.93–0.97 Å.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

4,5-bis(ferrocenylmethylthio)-1,3-dithiole-2-one

Crystal data

[Fe2(C5H5)2(C15H12OS4)]	F(000) = 1184
Mr = 578.37	Dx = 1.608 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.953 (2) Å	Cell parameters from 4915 reflections
b = 18.433 (4) Å	θ = 2.0–28.3°
c = 11.954 (2) Å	µ = 1.58 mm^−1
β = 114.86 (3)°	T = 150 K
V = 2389.8 (8) Å^3	Plate, orange
Z = 4	0.40 × 0.35 × 0.10 mm

Data collection

KappaCCD diffractometer	5785 independent reflections
Radiation source: fine-focus sealed X-ray tube	2658 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ϕ scans and ω scans with κ offsets	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan SORTAV (Blessing, 1995, 1997)	h = −15→13
Tmin = 0.571, Tmax = 0.901	k = −17→24
34055 measured reflections	l = −13→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.066P)^2] where P = (Fo^2 + 2Fc^2)/3
5785 reflections	(Δ/σ)max = 0.004
289 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.62 e Å^−3

Special details

Experimental. KappaCCD diffractometer using the following programs. COLLECT, Data collection software, Hooft (1999) [Hooft, R. (1998). Nonius BV, Delft, The Netherlands] is a graphical user interface written by Enraf–Nonius which encompasses the following programs. DENZO (Otwinowski & Minor, 1997) and indexing and data collection software package and a scaling package, SCALEPACK both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAVv package (Blessing, 1995, 1997) within the maXus suite of programs (Mackay et al., 1998) [Mackay, S., Gilmore, C·J., Edwards, C., Tremayne, M., Stewart, N. & Shankland, K. (1998). maXus. University of Glasgow, Scotland, UK]. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. Low-temperature data is collected using an Oxford Cryosystems Cryostream Cooler (Cosier and Glazer, 1986) [Cosier, J. & Glazer, A·M. (1986). J. Appl. Cryst. 19, 105–107].

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

	x	y	z	Uiso*/Ueq
Fe1	−0.29941 (6)	0.25505 (4)	0.29850 (6)	0.0566 (2)
C6	−0.2830 (4)	0.1621 (2)	0.2160 (4)	0.0482 (11)
C7	−0.2690 (4)	0.2227 (3)	0.1504 (4)	0.0542 (12)
C8	−0.1701 (4)	0.2648 (3)	0.2307 (5)	0.0657 (14)
C9	−0.1195 (4)	0.2292 (3)	0.3455 (5)	0.0708 (15)
C10	−0.1895 (4)	0.1660 (3)	0.3356 (4)	0.0585 (12)
C11	−0.4692 (6)	0.2536 (4)	0.3006 (8)	0.096 (2)
C12	−0.4609 (6)	0.3118 (4)	0.2347 (6)	0.0880 (18)
C13	−0.3666 (6)	0.3554 (3)	0.3102 (7)	0.0832 (17)
C14	−0.3106 (7)	0.3232 (5)	0.4270 (7)	0.108 (2)
C15	−0.3780 (8)	0.2571 (4)	0.4192 (7)	0.101 (2)
Fe2	0.23686 (5)	0.06832 (4)	0.40033 (5)	0.0491 (2)
C16	0.1729 (4)	0.1307 (3)	0.2453 (4)	0.0553 (12)
C17	0.2296 (5)	0.1742 (3)	0.3495 (5)	0.0689 (14)
C18	0.3518 (6)	0.1513 (4)	0.4123 (5)	0.094 (2)
C19	0.3688 (5)	0.0944 (4)	0.3461 (6)	0.098 (2)
C20	0.2593 (5)	0.0818 (3)	0.2415 (5)	0.0683 (14)
C21	0.0953 (5)	0.0268 (3)	0.4331 (5)	0.0770 (16)
C22	0.1827 (8)	0.0588 (4)	0.5383 (6)	0.098 (2)
C23	0.2943 (7)	0.0243 (4)	0.5686 (5)	0.104 (3)
C24	0.2746 (5)	−0.0309 (3)	0.4820 (6)	0.0824 (17)
C25	0.1506 (5)	−0.0271 (3)	0.3990 (4)	0.0676 (15)
S1	−0.32007 (11)	0.02516 (7)	0.10942 (11)	0.0612 (4)
S2	−0.04135 (11)	0.05923 (8)	0.12090 (13)	0.0760 (4)
S3	−0.41854 (11)	0.09068 (8)	−0.14281 (12)	0.0713 (4)
S4	−0.17445 (12)	0.12700 (8)	−0.12924 (11)	0.0683 (4)
O1	−0.3823 (4)	0.1598 (2)	−0.3176 (3)	0.1018 (14)
C1	−0.2911 (4)	0.0664 (2)	−0.0068 (4)	0.0479 (11)
C2	−0.1799 (4)	0.0839 (2)	−0.0020 (4)	0.0508 (11)
C3	−0.3355 (5)	0.1317 (3)	−0.2179 (4)	0.0704 (15)
C4	−0.3770 (4)	0.1034 (2)	0.1645 (4)	0.0588 (12)
C5	0.0426 (4)	0.1425 (3)	0.1518 (5)	0.0841 (18)
H7	−0.3173	0.2330	0.0678	0.065*
H8	−0.1429	0.3084	0.2116	0.079*
H9	−0.0520	0.2446	0.4154	0.085*
H10	−0.1758	0.1324	0.3981	0.070*
H11	−0.5277	0.2169	0.2703	0.115*
H12	−0.5110	0.3205	0.1519	0.106*
H13	−0.3436	0.3993	0.2877	0.100*
H14	−0.2437	0.3408	0.4955	0.130*
H15	−0.3629	0.2234	0.4818	0.122*
H17	0.1925	0.2119	0.3732	0.083*
H18	0.4106	0.1707	0.4851	0.113*
H19	0.4418	0.0686	0.3677	0.118*
H20	0.2468	0.0471	0.1809	0.082*
H21	0.0129	0.0402	0.3929	0.092*
H22	0.1687	0.0972	0.5813	0.117*
H23	0.3687	0.0357	0.6344	0.124*
H24	0.3328	−0.0638	0.4801	0.099*
H25	0.1122	−0.0570	0.3308	0.081*
H4A	−0.4490	0.1229	0.0968	0.071*
H4B	−0.4022	0.0874	0.2278	0.071*
H5A	0.0430	0.1612	0.0762	0.101*
H5B	0.0028	0.1780	0.1828	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0713 (4)	0.0467 (5)	0.0683 (5)	0.0008 (3)	0.0454 (4)	0.0024 (3)
C6	0.054 (2)	0.048 (3)	0.053 (3)	0.006 (2)	0.033 (2)	0.005 (2)
C7	0.057 (3)	0.060 (3)	0.053 (3)	0.003 (2)	0.031 (2)	0.006 (2)
C8	0.069 (3)	0.059 (4)	0.089 (4)	−0.008 (3)	0.053 (3)	0.002 (3)
C9	0.054 (3)	0.084 (4)	0.070 (3)	−0.006 (3)	0.022 (3)	−0.009 (3)
C10	0.062 (3)	0.057 (3)	0.055 (3)	0.008 (2)	0.024 (2)	0.011 (2)
C11	0.112 (5)	0.072 (5)	0.149 (7)	0.007 (4)	0.100 (5)	0.009 (5)
C12	0.097 (4)	0.072 (5)	0.121 (5)	0.024 (4)	0.072 (4)	0.005 (4)
C13	0.106 (5)	0.047 (4)	0.129 (5)	0.000 (3)	0.081 (4)	−0.007 (4)
C14	0.136 (6)	0.114 (7)	0.098 (5)	0.007 (5)	0.071 (5)	−0.039 (5)
C15	0.171 (7)	0.077 (5)	0.110 (5)	0.038 (5)	0.111 (6)	0.028 (4)
Fe2	0.0452 (3)	0.0511 (4)	0.0468 (4)	−0.0096 (3)	0.0153 (3)	0.0054 (3)
C16	0.048 (3)	0.064 (3)	0.053 (3)	−0.014 (2)	0.020 (2)	0.011 (2)
C17	0.094 (4)	0.042 (3)	0.083 (3)	−0.011 (3)	0.049 (3)	0.004 (3)
C18	0.078 (4)	0.108 (6)	0.071 (4)	−0.058 (4)	0.007 (3)	0.020 (4)
C19	0.051 (3)	0.129 (6)	0.121 (6)	0.011 (3)	0.042 (4)	0.057 (5)
C20	0.076 (4)	0.075 (4)	0.066 (3)	−0.005 (3)	0.042 (3)	0.010 (3)
C21	0.083 (4)	0.079 (5)	0.086 (4)	−0.007 (3)	0.052 (4)	0.023 (3)
C22	0.172 (7)	0.071 (5)	0.082 (5)	−0.032 (5)	0.086 (5)	−0.012 (4)
C23	0.123 (6)	0.100 (6)	0.049 (3)	−0.053 (5)	−0.001 (4)	0.023 (4)
C24	0.079 (4)	0.060 (4)	0.102 (4)	0.004 (3)	0.031 (4)	0.032 (3)
C25	0.080 (4)	0.059 (4)	0.054 (3)	−0.027 (3)	0.020 (3)	0.005 (3)
S1	0.0657 (7)	0.0462 (8)	0.0722 (8)	−0.0011 (6)	0.0295 (6)	0.0047 (6)
S2	0.0508 (7)	0.0678 (10)	0.0803 (9)	−0.0024 (6)	−0.0010 (7)	0.0228 (7)
S3	0.0513 (7)	0.0797 (10)	0.0600 (8)	0.0048 (6)	0.0010 (6)	0.0007 (7)
S4	0.0711 (8)	0.0751 (10)	0.0585 (7)	0.0049 (7)	0.0271 (7)	0.0099 (7)
O1	0.118 (3)	0.108 (4)	0.049 (2)	0.008 (3)	0.006 (2)	0.022 (2)
C1	0.045 (2)	0.049 (3)	0.041 (2)	0.003 (2)	0.0104 (19)	−0.004 (2)
C2	0.054 (3)	0.049 (3)	0.043 (2)	0.002 (2)	0.014 (2)	0.000 (2)
C3	0.081 (3)	0.064 (4)	0.046 (3)	0.011 (3)	0.008 (3)	−0.005 (2)
C4	0.060 (3)	0.053 (3)	0.071 (3)	0.006 (2)	0.035 (2)	0.006 (2)
C5	0.067 (3)	0.081 (4)	0.081 (4)	−0.012 (3)	0.009 (3)	0.023 (3)

Geometric parameters (Å, º)

Fe1—C15	2.026 (6)	Fe2—C25	2.035 (5)
Fe1—C6	2.027 (4)	Fe2—C17	2.035 (5)
Fe1—C14	2.032 (6)	Fe2—C16	2.037 (4)
Fe1—C10	2.032 (5)	Fe2—C21	2.039 (5)
Fe1—C8	2.032 (4)	Fe2—C20	2.041 (5)
Fe1—C9	2.037 (5)	C16—C20	1.386 (7)
Fe1—C7	2.040 (4)	C16—C17	1.395 (7)
Fe1—C11	2.040 (6)	C16—C5	1.503 (6)
Fe1—C12	2.041 (6)	C17—C18	1.398 (8)
Fe1—C13	2.045 (5)	C18—C19	1.378 (9)
C6—C10	1.397 (6)	C19—C20	1.399 (8)
C6—C7	1.414 (6)	C21—C25	1.349 (7)
C6—C4	1.494 (6)	C21—C22	1.384 (8)
C7—C8	1.402 (6)	C22—C23	1.381 (9)
C8—C9	1.407 (7)	C23—C24	1.400 (9)
C9—C10	1.410 (7)	C24—C25	1.396 (7)
C11—C12	1.359 (8)	S1—C1	1.742 (5)
C11—C15	1.379 (9)	S1—C4	1.831 (5)
C12—C13	1.370 (8)	S2—C2	1.750 (4)
C13—C14	1.401 (8)	S2—C5	1.785 (5)
C14—C15	1.441 (9)	S3—C1	1.756 (4)
Fe2—C19	2.000 (6)	S3—C3	1.765 (6)
Fe2—C23	2.004 (5)	S4—C2	1.741 (5)
Fe2—C22	2.016 (6)	S4—C3	1.766 (5)
Fe2—C18	2.020 (5)	O1—C3	1.200 (5)
Fe2—C24	2.033 (5)	C1—C2	1.345 (6)
C15—Fe1—C6	122.1 (2)	C22—Fe2—C24	67.2 (3)
C15—Fe1—C14	41.6 (3)	C18—Fe2—C24	129.8 (3)
C6—Fe1—C14	160.2 (3)	C19—Fe2—C25	132.2 (3)
C15—Fe1—C10	108.1 (2)	C23—Fe2—C25	67.5 (2)
C6—Fe1—C10	40.27 (17)	C22—Fe2—C25	66.2 (2)
C14—Fe1—C10	125.2 (3)	C18—Fe2—C25	169.0 (3)
C15—Fe1—C8	160.1 (3)	C24—Fe2—C25	40.1 (2)
C6—Fe1—C8	68.63 (19)	C19—Fe2—C17	67.2 (3)
C14—Fe1—C8	123.3 (3)	C23—Fe2—C17	129.9 (3)
C10—Fe1—C8	68.2 (2)	C22—Fe2—C17	109.8 (2)
C15—Fe1—C9	124.0 (3)	C18—Fe2—C17	40.3 (2)
C6—Fe1—C9	68.24 (19)	C24—Fe2—C17	168.3 (2)
C14—Fe1—C9	109.5 (3)	C25—Fe2—C17	150.3 (2)
C10—Fe1—C9	40.55 (19)	C19—Fe2—C16	67.3 (2)
C8—Fe1—C9	40.47 (19)	C23—Fe2—C16	168.8 (3)
C15—Fe1—C7	158.2 (3)	C22—Fe2—C16	131.8 (3)
C6—Fe1—C7	40.71 (16)	C18—Fe2—C16	67.8 (2)
C14—Fe1—C7	158.3 (3)	C24—Fe2—C16	150.1 (2)
C10—Fe1—C7	67.57 (18)	C25—Fe2—C16	119.03 (18)
C8—Fe1—C7	40.29 (18)	C17—Fe2—C16	40.08 (19)
C9—Fe1—C7	67.57 (19)	C19—Fe2—C21	169.6 (3)
C15—Fe1—C11	39.6 (3)	C23—Fe2—C21	67.5 (2)
C6—Fe1—C11	107.2 (2)	C22—Fe2—C21	39.9 (2)
C14—Fe1—C11	67.4 (3)	C18—Fe2—C21	149.9 (3)
C10—Fe1—C11	122.8 (2)	C24—Fe2—C21	66.7 (2)
C8—Fe1—C11	158.9 (3)	C25—Fe2—C21	38.7 (2)
C9—Fe1—C11	159.0 (3)	C17—Fe2—C21	118.8 (2)
C7—Fe1—C11	123.2 (3)	C16—Fe2—C21	111.2 (2)
C15—Fe1—C12	66.9 (3)	C19—Fe2—C20	40.5 (2)
C6—Fe1—C12	121.4 (2)	C23—Fe2—C20	149.3 (3)
C14—Fe1—C12	67.2 (3)	C22—Fe2—C20	169.8 (3)
C10—Fe1—C12	156.8 (2)	C18—Fe2—C20	67.8 (2)
C8—Fe1—C12	124.3 (2)	C24—Fe2—C20	117.8 (2)
C9—Fe1—C12	161.1 (3)	C25—Fe2—C20	111.2 (2)
C7—Fe1—C12	108.1 (2)	C17—Fe2—C20	67.2 (2)
C11—Fe1—C12	38.9 (2)	C16—Fe2—C20	39.72 (19)
C15—Fe1—C13	67.7 (2)	C21—Fe2—C20	131.9 (2)
C6—Fe1—C13	156.8 (2)	C20—C16—C17	108.4 (4)
C14—Fe1—C13	40.2 (2)	C20—C16—C5	128.6 (5)
C10—Fe1—C13	162.3 (3)	C17—C16—C5	122.9 (5)
C8—Fe1—C13	109.5 (2)	C20—C16—Fe2	70.3 (3)
C9—Fe1—C13	126.3 (2)	C17—C16—Fe2	69.9 (3)
C7—Fe1—C13	122.8 (2)	C5—C16—Fe2	129.3 (3)
C11—Fe1—C13	65.7 (2)	C16—C17—C18	108.1 (5)
C12—Fe1—C13	39.2 (2)	C16—C17—Fe2	70.0 (3)
C10—C6—C7	107.3 (4)	C18—C17—Fe2	69.2 (3)
C10—C6—C4	126.7 (4)	C19—C18—C17	107.2 (5)
C7—C6—C4	126.0 (4)	C19—C18—Fe2	69.2 (3)
C10—C6—Fe1	70.1 (3)	C17—C18—Fe2	70.4 (3)
C7—C6—Fe1	70.1 (3)	C18—C19—C20	109.4 (5)
C4—C6—Fe1	127.1 (3)	C18—C19—Fe2	70.7 (3)
C8—C7—C6	108.6 (4)	C20—C19—Fe2	71.4 (3)
C8—C7—Fe1	69.6 (3)	C16—C20—C19	107.0 (5)
C6—C7—Fe1	69.1 (2)	C16—C20—Fe2	70.0 (3)
C7—C8—C9	107.6 (4)	C19—C20—Fe2	68.2 (3)
C7—C8—Fe1	70.1 (3)	C25—C21—C22	108.1 (6)
C9—C8—Fe1	69.9 (3)	C25—C21—Fe2	70.5 (3)
C8—C9—C10	107.9 (4)	C22—C21—Fe2	69.2 (3)
C8—C9—Fe1	69.6 (3)	C23—C22—C21	108.6 (6)
C10—C9—Fe1	69.5 (3)	C23—C22—Fe2	69.4 (4)
C6—C10—C9	108.6 (4)	C21—C22—Fe2	70.9 (3)
C6—C10—Fe1	69.7 (3)	C22—C23—C24	107.3 (5)
C9—C10—Fe1	69.9 (3)	C22—C23—Fe2	70.4 (3)
C12—C11—C15	109.9 (7)	C24—C23—Fe2	70.8 (3)
C12—C11—Fe1	70.6 (3)	C25—C24—C23	106.7 (6)
C15—C11—Fe1	69.6 (4)	C25—C24—Fe2	70.0 (3)
C11—C12—C13	108.7 (6)	C23—C24—Fe2	68.6 (3)
C11—C12—Fe1	70.5 (4)	C21—C25—C24	109.3 (5)
C13—C12—Fe1	70.6 (3)	C21—C25—Fe2	70.8 (3)
C12—C13—C14	108.9 (6)	C24—C25—Fe2	69.8 (3)
C12—C13—Fe1	70.2 (3)	C1—S1—C4	99.9 (2)
C14—C13—Fe1	69.4 (3)	C2—S2—C5	101.6 (2)
C13—C14—C15	105.9 (6)	C1—S3—C3	97.2 (2)
C13—C14—Fe1	70.4 (3)	C2—S4—C3	96.6 (2)
C15—C14—Fe1	69.0 (3)	C2—C1—S1	126.5 (3)
C11—C15—C14	106.5 (6)	C2—C1—S3	115.8 (3)
C11—C15—Fe1	70.7 (3)	S1—C1—S3	117.6 (2)
C14—C15—Fe1	69.4 (3)	C1—C2—S4	118.1 (3)
C19—Fe2—C23	116.0 (3)	C1—C2—S2	122.9 (3)
C19—Fe2—C22	148.6 (3)	S4—C2—S2	118.8 (3)
C23—Fe2—C22	40.2 (3)	O1—C3—S3	124.2 (4)
C19—Fe2—C18	40.1 (2)	O1—C3—S4	123.6 (5)
C23—Fe2—C18	107.4 (2)	S3—C3—S4	112.2 (3)
C22—Fe2—C18	116.8 (3)	C6—C4—S1	113.0 (3)
C19—Fe2—C24	109.0 (3)	C16—C5—S2	110.3 (4)
C23—Fe2—C24	40.6 (2)