Bis­[N-(2-hydroxy­ethyl)-N-methyl­di­thiocarbamato-S,S']­di­phenyl­tin

The Sn atom in the title compound, [Sn(C₆H₅)₂(C₄H₈NOS₂)₂], is six-coordinate in a cis-C₂SnS₄ octahedral environment.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.054
• wR factor = 0.146
• Data-to-parameter ratio = 23.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_320  Alert C Check Hybridisation of  C(15)  in main residue          ?

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(15)  -   C(16)  =       1.41 Ang.

PLAT_601  Alert C Structure contains solvent accessible VOIDS of      32.00 A   3

PLAT_732  Alert C Angle   Calc    67.80(4), Rep   67.80(10) ....       2.50 s.u-Ratio
                     S3   -SN1  -S4      1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

---

S1. Comment

Six-coordinate bis-chelated diaryltin compounds generally adopt a cis-octahedral geometry (Ng et al., 1987). The bond dimensions of the Sn atom in the title compound, (I), are similar to those found in the symmetrical compound, diphenyltin bis[bis(2-hydroxyethyl)dithiocarbamate] (Farina et al., 2000).

S2. Experimental

A solution of carbon disulfide in methanol was added to a mixture of diphenyltin dichloride and 2-hydroxyethylmethylamine (1:2 molar stoichiometry) at 277 K. The mixture was stirred to afford a pale-yellow solid, which was collected and recrystallized from a methanol/chloroform mixture to afford the title compound (m.p. 401–402 K). Elemental analysis, found (calculated) for C₂₀H₂₆N₂O₂S₄Sn: C 40.40 (41.90), H 4.83 (4.57), N 5.24 (4.89), Sn 20.88% (20.70%).

S3. Refinement

One of the two hydroxyethyl groups is disordered. The N—C distance was DFIXed at 1.47±0.01 Å, the C—C distance at 1.54±0.01 Å and the C—O distance at 1.43±0.01 Å; the S1/S2/C13/N1/C14/C15 system was restrained to be planar by FLAT 0.01.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound at the 50% probability level. H atoms are shown as circles of arbitrary radii.

Diphenylbis[N-(2-hydroxyethyl)-N-methyldithiocarbamato]tin

Crystal data

[Sn(C6H5)2(C4H8NOS2)]	F(000) = 1160
Mr = 573.36	Dx = 1.532 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9931 (1) Å	Cell parameters from 8192 reflections
b = 12.2068 (1) Å	θ = 1.7–28.3°
c = 22.6703 (3) Å	µ = 1.38 mm^−1
β = 92.507 (1)°	T = 298 K
V = 2486.29 (5) Å^3	Block, colorless
Z = 4	0.26 × 0.22 × 0.16 mm

Data collection

Siemens CCD area-detector diffractometer	6025 independent reflections
Radiation source: fine-focus sealed tube	4060 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.7°
ω scans	h = −11→11
Absorption correction: empirical (SADABS; Sheldrick, 1996)	k = −11→16
Tmin = 0.715, Tmax = 0.809	l = −30→22
17084 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	Riding
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0636P)^2] where P = (Fo^2 + 2Fc^2)/3
6025 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 1.22 e Å^−3
6 restraints	Δρmin = −1.77 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.17456 (4)	0.78194 (3)	0.42776 (2)	0.0349 (1)
S1	0.2827 (2)	0.6240 (1)	0.36459 (7)	0.0484 (4)
S2	0.4278 (2)	0.7060 (1)	0.47491 (7)	0.0483 (4)
S3	0.1238 (2)	0.8751 (1)	0.52551 (6)	0.0494 (4)
S4	0.0492 (2)	0.6414 (1)	0.50616 (7)	0.0481 (4)
N1	0.5553 (5)	0.5669 (3)	0.4037 (2)	0.060 (1)
N2	−0.0205 (6)	0.7524 (4)	0.6013 (2)	0.051 (1)
O1	0.6106 (6)	0.3501 (5)	0.2909 (3)	0.095 (2)
O2	0.1249 (7)	0.7528 (5)	0.7169 (2)	0.101 (2)
C1	−0.0402 (5)	0.7854 (4)	0.3808 (2)	0.038 (1)
C2	−0.1537 (6)	0.8506 (5)	0.4017 (3)	0.057 (2)
C3	−0.2905 (7)	0.8563 (6)	0.3722 (4)	0.068 (2)
C4	−0.3172 (7)	0.7974 (6)	0.3210 (3)	0.064 (2)
C5	−0.2080 (8)	0.7349 (6)	0.2990 (3)	0.065 (2)
C6	−0.0682 (6)	0.7273 (5)	0.3290 (3)	0.053 (2)
C7	0.2874 (5)	0.9229 (4)	0.3915 (2)	0.040 (1)
C8	0.2880 (6)	0.9347 (5)	0.3311 (3)	0.046 (1)
C9	0.3585 (7)	1.0229 (5)	0.3058 (3)	0.060 (2)
C10	0.4252 (7)	1.1009 (5)	0.3411 (4)	0.065 (2)
C11	0.4238 (8)	1.0912 (6)	0.4018 (3)	0.068 (2)
C12	0.3569 (7)	1.0027 (5)	0.4268 (3)	0.054 (2)
C13	0.4346 (5)	0.6266 (3)	0.4131 (2)	0.042 (1)
C14	0.6864 (6)	0.5692 (5)	0.4442 (3)	0.069 (2)
C15	0.5698 (9)	0.4996 (5)	0.3503 (3)	0.134 (5)
C16	0.579 (1)	0.3842 (7)	0.3486 (4)	0.158 (6)
C17	0.0435 (6)	0.7545 (4)	0.5495 (2)	0.041 (1)
C18	−0.0934 (9)	0.6534 (7)	0.6232 (4)	0.094 (3)
C19	−0.0220 (7)	0.8491 (6)	0.6391 (3)	0.062 (2)
C20	0.1133 (8)	0.8515 (7)	0.6796 (3)	0.076 (2)
H1a	0.7030	0.3819	0.2799	0.142*
H2a	0.2130	0.7572	0.7422	0.151*
H2	−0.1368	0.8909	0.4361	0.068*
H3	−0.3651	0.9001	0.3868	0.082*
H4	−0.4103	0.8005	0.3016	0.077*
H5	−0.2257	0.6967	0.2639	0.078*
H6	0.0057	0.6833	0.3140	0.063*
H8	0.2405	0.8828	0.3069	0.055*
H9	0.3603	1.0290	0.2650	0.072*
H10	0.4715	1.1607	0.3242	0.078*
H11	0.4684	1.1448	0.4258	0.082*
H12	0.3580	0.9960	0.4676	0.065*
H14a	0.7649	0.5272	0.4278	0.104*
H14b	0.6617	0.5383	0.4815	0.104*
H14c	0.7187	0.6435	0.4499	0.104*
H15a	0.4860	0.5191	0.3240	0.161*
H15b	0.6580	0.5262	0.3318	0.161*
H16a	0.4854	0.3526	0.3598	0.190*
H16b	0.6567	0.3591	0.3763	0.190*
H18a	−0.1325	0.6682	0.6611	0.140*
H18b	−0.0222	0.5950	0.6267	0.140*
H18c	−0.1732	0.6325	0.5959	0.140*
H19a	−0.1104	0.8481	0.6622	0.074*
H19b	−0.0251	0.9146	0.6149	0.074*
H20a	0.2011	0.8572	0.6564	0.091*
H20b	0.1098	0.9158	0.7047	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0321 (2)	0.0368 (2)	0.0354 (2)	0.0027 (1)	−0.0016 (1)	−0.0037 (2)
S1	0.0383 (7)	0.0530 (8)	0.0525 (8)	0.0132 (6)	−0.0146 (6)	−0.0164 (7)
S2	0.0432 (8)	0.0571 (9)	0.0435 (8)	0.0086 (6)	−0.0120 (6)	−0.0082 (7)
S3	0.070 (1)	0.0382 (7)	0.0408 (8)	−0.0021 (7)	0.0120 (7)	−0.0056 (6)
S4	0.0485 (8)	0.0378 (7)	0.0573 (9)	0.0002 (6)	−0.0077 (7)	0.0012 (7)
N1	0.045 (3)	0.063 (3)	0.070 (4)	0.023 (2)	−0.020 (3)	−0.022 (3)
N2	0.047 (3)	0.059 (3)	0.048 (3)	0.001 (2)	0.010 (2)	0.006 (2)
O1	0.085 (4)	0.110 (4)	0.091 (4)	0.006 (3)	0.027 (3)	−0.048 (4)
O2	0.084 (4)	0.167 (6)	0.051 (3)	0.025 (4)	−0.003 (3)	0.024 (4)
C1	0.025 (2)	0.046 (3)	0.041 (3)	−0.001 (2)	−0.003 (2)	0.008 (2)
C2	0.043 (3)	0.048 (3)	0.078 (4)	0.008 (3)	−0.009 (3)	−0.007 (3)
C3	0.039 (3)	0.066 (4)	0.099 (6)	0.020 (3)	0.003 (4)	0.015 (4)
C4	0.037 (3)	0.086 (5)	0.068 (4)	0.006 (3)	−0.009 (3)	0.022 (4)
C5	0.055 (4)	0.096 (5)	0.044 (3)	−0.004 (4)	−0.014 (3)	0.004 (4)
C6	0.032 (3)	0.085 (4)	0.040 (3)	0.005 (3)	−0.004 (2)	−0.003 (3)
C7	0.031 (3)	0.044 (3)	0.044 (3)	0.002 (2)	0.004 (2)	−0.004 (2)
C8	0.040 (3)	0.049 (3)	0.047 (3)	−0.001 (2)	0.005 (3)	−0.006 (3)
C9	0.048 (3)	0.076 (4)	0.056 (4)	0.009 (3)	0.016 (3)	0.006 (3)
C10	0.052 (4)	0.051 (4)	0.093 (6)	−0.008 (3)	0.014 (4)	0.010 (4)
C11	0.061 (4)	0.059 (4)	0.084 (5)	−0.018 (3)	−0.005 (4)	−0.006 (4)
C12	0.050 (3)	0.059 (4)	0.053 (4)	−0.006 (3)	−0.003 (3)	−0.003 (3)
C13	0.036 (3)	0.040 (3)	0.048 (3)	0.003 (2)	−0.002 (2)	−0.003 (2)
C14	0.043 (3)	0.074 (4)	0.089 (5)	0.022 (3)	−0.025 (4)	−0.008 (4)
C15	0.086 (7)	0.134 (9)	0.18 (1)	0.053 (6)	−0.068 (7)	−0.057 (9)
C16	0.13 (1)	0.118 (9)	0.23 (2)	−0.040 (8)	−0.03 (1)	0.06 (1)
C17	0.035 (3)	0.048 (3)	0.041 (3)	0.007 (2)	−0.001 (2)	0.005 (2)
C18	0.087 (6)	0.100 (6)	0.097 (6)	−0.030 (5)	0.036 (5)	0.015 (5)
C19	0.052 (4)	0.091 (5)	0.043 (3)	0.022 (3)	0.011 (3)	−0.003 (3)
C20	0.073 (5)	0.100 (6)	0.056 (4)	0.000 (4)	0.015 (4)	−0.017 (4)

Geometric parameters (Å, º)

Sn1—C1	2.164 (5)	C15—C16	1.411 (8)
Sn1—C7	2.177 (5)	C19—C20	1.49 (1)
Sn1—S1	2.614 (1)	O1—H1a	0.9600
Sn1—S2	2.641 (1)	O2—H2a	0.9600
Sn1—S3	2.550 (1)	C2—H2	0.9300
Sn1—S4	2.748 (2)	C3—H3	0.9300
S1—C13	1.717 (6)	C4—H4	0.9300
S2—C13	1.706 (6)	C5—H5	0.9300
S3—C17	1.737 (6)	C6—H6	0.9300
S4—C17	1.697 (6)	C8—H8	0.9300
N1—C13	1.332 (7)	C9—H9	0.9300
N1—C14	1.463 (8)	C10—H10	0.9300
N1—C15	1.474 (7)	C11—H11	0.9300
N2—C17	1.331 (7)	C12—H12	0.9300
N2—C19	1.459 (8)	C14—H14a	0.9600
N2—C18	1.471 (8)	C14—H14b	0.9600
O1—C16	1.412 (8)	C14—H14c	0.9600
O2—C20	1.473 (9)	C15—H15a	0.9700
C1—C6	1.386 (8)	C15—H15b	0.9700
C1—C2	1.393 (7)	C16—H16a	0.9700
C2—C3	1.376 (9)	C16—H16b	0.9700
C3—C4	1.38 (1)	C18—H18a	0.9600
C4—C5	1.356 (9)	C18—H18b	0.9600
C5—C6	1.406 (8)	C18—H18c	0.9600
C8—C9	1.386 (8)	C19—H19a	0.9700
C9—C10	1.365 (9)	C19—H19b	0.9700
C10—C11	1.38 (1)	C20—H20a	0.9700
C11—C12	1.370 (9)	C20—H20b	0.9700
C1—Sn1—C7	102.7 (2)	C3—C2—H2	119.4
C1—Sn1—S1	95.2 (1)	C1—C2—H2	119.4
C1—Sn1—S2	160.2 (1)	C2—C3—H3	119.9
C1—Sn1—S3	103.2 (1)	C4—C3—H3	119.9
C1—Sn1—S4	87.0 (1)	C5—C4—H4	119.9
C7—Sn1—S1	100.7 (1)	C3—C4—H4	119.9
C7—Sn1—S2	91.3 (1)	C4—C5—H5	119.8
C7—Sn1—S3	94.6 (1)	C6—C5—H5	119.8
C7—Sn1—S4	161.6 (2)	C1—C6—H6	119.9
S1—Sn1—S2	68.2 (1)	C5—C6—H6	119.9
S1—Sn1—S3	152.9 (1)	C7—C8—H8	119.6
S1—Sn1—S4	93.8 (1)	C9—C8—H8	119.6
S2—Sn1—S3	89.4 (1)	C10—C9—H9	120.1
S2—Sn1—S4	83.7 (1)	C8—C9—H9	120.1
S3—Sn1—S4	67.8 (1)	C9—C10—H10	120.0
C13—S1—Sn1	86.6 (2)	C11—C10—H10	120.0
C13—S2—Sn1	85.9 (2)	C12—C11—H11	119.9
C17—S3—Sn1	89.2 (2)	C10—C11—H11	119.9
C17—S4—Sn1	83.7 (2)	C11—C12—H12	119.7
C13—N1—C14	122.0 (5)	C7—C12—H12	119.7
C13—N1—C15	122.6 (6)	N1—C14—H14a	109.5
C14—N1—C15	115.3 (5)	N1—C14—H14b	109.5
C17—N2—C19	121.2 (5)	H14a—C14—H14b	109.5
C17—N2—C18	122.0 (6)	N1—C14—H14c	109.5
C19—N2—C18	116.8 (5)	H14a—C14—H14c	109.5
C6—C1—C2	118.1 (5)	H14b—C14—H14c	109.5
C6—C1—Sn1	122.1 (4)	C16—C15—H15a	105.8
C2—C1—Sn1	119.7 (4)	N1—C15—H15a	105.8
C3—C2—C1	121.2 (6)	C16—C15—H15b	105.8
C2—C3—C4	120.1 (6)	N1—C15—H15b	105.8
C5—C4—C3	120.1 (6)	H15a—C15—H15b	106.2
C4—C5—C6	120.4 (6)	C15—C16—H16a	109.8
C1—C6—C5	120.1 (6)	O1—C16—H16a	109.8
C8—C7—C12	118.5 (5)	C15—C16—H16b	109.8
C8—C7—Sn1	118.7 (4)	O1—C16—H16b	109.8
C12—C7—Sn1	122.8 (4)	H16a—C16—H16b	108.2
C7—C8—C9	120.9 (6)	N2—C18—H18a	109.5
C10—C9—C8	119.9 (6)	N2—C18—H18b	109.5
C9—C10—C11	120.0 (6)	H18a—C18—H18b	109.5
C12—C11—C10	120.1 (6)	N2—C18—H18c	109.5
C11—C12—C7	120.6 (6)	H18a—C18—H18c	109.5
N1—C13—S2	120.1 (4)	H18b—C18—H18c	109.5
N1—C13—S1	121.2 (4)	N2—C19—H19a	109.6
S2—C13—S1	118.7 (3)	C20—C19—H19a	109.6
C16—C15—N1	125.9 (6)	N2—C19—H19b	109.6
C15—C16—O1	109.5 (8)	C20—C19—H19b	109.6
N2—C17—S4	121.3 (4)	H19a—C19—H19b	108.1
N2—C17—S3	119.6 (4)	O2—C20—H20a	109.3
S4—C17—S3	119.0 (3)	C19—C20—H20a	109.3
N2—C19—C20	110.5 (5)	O2—C20—H20b	109.3
O2—C20—C19	111.8 (6)	C19—C20—H20b	109.3
C16—O1—H1a	109.5	H20a—C20—H20b	107.9
C20—O2—H2a	109.5
C1—Sn1—S1—C13	−173.8 (1)	S3—Sn1—C7—C8	−154.3 (4)
C7—Sn1—S1—C13	82.2 (2)	S1—Sn1—C7—C8	48.2 (4)
S3—Sn1—S1—C13	−40.9 (1)	S2—Sn1—C7—C8	116.2 (4)
S2—Sn1—S1—C13	−4.8 (1)	S4—Sn1—C7—C8	−170.1 (3)
S4—Sn1—S1—C13	−86.5 (1)	C1—Sn1—C7—C12	129.2 (5)
C1—Sn1—S2—C13	39.2 (4)	S3—Sn1—C7—C12	24.6 (5)
C7—Sn1—S2—C13	−96.1 (2)	S1—Sn1—C7—C12	−132.9 (4)
S3—Sn1—S2—C13	169.3 (1)	S2—Sn1—C7—C12	−64.9 (5)
S1—Sn1—S2—C13	4.9 (1)	S4—Sn1—C7—C12	8.7 (8)
S4—Sn1—S2—C13	101.6 (1)	C12—C7—C8—C9	1.2 (8)
C1—Sn1—S3—C17	78.1 (2)	Sn1—C7—C8—C9	−179.9 (4)
C7—Sn1—S3—C17	−177.7 (2)	C7—C8—C9—C10	−1.7 (9)
S1—Sn1—S3—C17	−53.4 (2)	C8—C9—C10—C11	1 (1)
S2—Sn1—S3—C17	−86.5 (2)	C9—C10—C11—C12	1 (1)
S4—Sn1—S3—C17	−3.0 (2)	C10—C11—C12—C7	−1 (1)
C1—Sn1—S4—C17	−102.5 (2)	C8—C7—C12—C11	0.2 (9)
C7—Sn1—S4—C17	20.2 (5)	Sn1—C7—C12—C11	−178.6 (5)
S3—Sn1—S4—C17	3.1 (2)	C14—N1—C13—S2	−1.8 (4)
S1—Sn1—S4—C17	162.5 (2)	C15—N1—C13—S2	−177.9 (2)
S2—Sn1—S4—C17	95.0 (2)	C14—N1—C13—S1	179.2 (2)
C7—Sn1—C1—C6	92.6 (5)	C15—N1—C13—S1	3.1 (4)
S3—Sn1—C1—C6	−169.5 (4)	Sn1—S2—C13—N1	173.1 (2)
S1—Sn1—C1—C6	−9.5 (5)	Sn1—S2—C13—S1	−7.9 (1)
S2—Sn1—C1—C6	−41.2 (7)	Sn1—S1—C13—N1	−173.1 (2)
S4—Sn1—C1—C6	−103.1 (4)	Sn1—S1—C13—S2	7.9 (1)
C7—Sn1—C1—C2	−85.2 (5)	C13—N1—C15—C16	−114.5 (9)
S3—Sn1—C1—C2	12.7 (5)	C14—N1—C15—C16	69 (1)
S1—Sn1—C1—C2	172.6 (4)	N1—C15—C16—O1	−172.7 (7)
S2—Sn1—C1—C2	140.9 (4)	C19—N2—C17—S4	178.5 (4)
S4—Sn1—C1—C2	79.0 (4)	C18—N2—C17—S4	−1.8 (9)
C6—C1—C2—C3	0.7 (9)	C19—N2—C17—S3	−1.3 (7)
Sn1—C1—C2—C3	178.7 (5)	C18—N2—C17—S3	178.5 (5)
C1—C2—C3—C4	0 (1)	Sn1—S4—C17—N2	175.4 (5)
C2—C3—C4—C5	−1 (1)	Sn1—S4—C17—S3	−4.9 (3)
C3—C4—C5—C6	2 (1)	Sn1—S3—C17—N2	−175.0 (4)
C2—C1—C6—C5	−0.1 (9)	Sn1—S3—C17—S4	5.2 (3)
Sn1—C1—C6—C5	−178.0 (5)	C17—N2—C19—C20	−89.2 (7)
C4—C5—C6—C1	−1 (1)	C18—N2—C19—C20	91.0 (7)
C1—Sn1—C7—C8	−49.6 (4)	N2—C19—C20—O2	−58.3 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1a···O2^i	0.96	2.26	2.703 (8)	107
O2—H2a···O1^i	0.96	2.21	2.703 (8)	110
C15—H15a···S1	0.97	2.44	3.025 (8)	118
C19—H19b···S3	0.97	2.52	2.958 (7)	107

Symmetry code: (i) −x+1, −y+1, −z+1.