[4-(Dimethyl­amino)­pyridine-κN1]tri­methyl(thio­cyanato-κN)tin(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536812022064

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m790

doi:10.1107/S1600536812022064

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[4-(Dimethylamino)pyridine-κN¹]trimethyl(thiocyanato-κN)tin(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 May 2012; accepted 16 May 2012; online 26 May 2012)

In the title monomeric trimethyltin(IV) isothiocyanate–4,4-dimethylpyridine adduct, [Sn(CH₃)₃(NCS)(C₇H₁₀N₂)], the Sn^IV atom shows a trans-C₃SnN₂ trigonal bipyramidal coordination. The Sn^IV atom lies out of the equatorial plane by 0.033 (4) Å in the direction of the donor N atom of the N-heterocycle. The crystal studied was a non-merohedral twin with a minor component of 48.8 (2)%.

Related literature

For trimethyltin isothiocyanate, see: Forder & Sheldrick (1970 ).

Experimental

Crystal data

[Sn(CH₃)₃(NCS)(C₇H₁₀N₂)]
M_r = 344.04
Monoclinic, P 2₁ /c
a = 7.2026 (4) Å
b = 13.4736 (8) Å
c = 14.9785 (8) Å
β = 93.792 (5)°
V = 1450.41 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.558, T_max = 0.650
15682 measured reflections
5542 independent reflections
4916 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.197
S = 1.23
5542 reflections
151 parameters
H-atom parameters constrained
Δρ_max = 1.61 e Å⁻³
Δρ_min = −1.98 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022064/nk2162sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022064/nk2162Isup2.hkl

checkCIF report

Comment top

Trimethyltin halides and pseudohalides are Lewis acids that form 1:1 complexes with aromatic amines. Trimethyltin isocyanate itself exists as a polymer in which the isocyanate anion bridges adjacent trimethyltin cations (Forder & Sheldrick, 1970). In the 4,4-dimethylpyridine adduct (Scheme I), the weaker tin–sulfur bond is disrupted, and the adduct is monomeric. The Sn^IV atom shows trans-C₃SnN₂ trigonal bipyramidal coordination. The tin atom lies out of the equatorial plane by 0.033 (4) Å in the direction of the donor N atom of the N-heterocycle.

Related literature top

For trimethyltin isothiocyanate, see: Forder & Sheldrick (1970).

Experimental top

Trimethyltin isothiocyanate (0.24 g, 1 mmol) and 4-(dimethylamino)pyridine (0.11 g, 1 mmol) were loaded into a convection tube and the tube was filled with methanol and kept at 333 K. Light yellow crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (CH₃)₃Sn(NCS)(C₇H₁₀N₂) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

[4-(Dimethylamino)pyridine-κN¹]trimethyl(thiocyanato- κN)tin(IV) top

Crystal data top

[Sn(CH₃)₃(NCS)(C₇H₁₀N₂)]	F(000) = 688
M_r = 344.04	D_x = 1.576 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5713 reflections
a = 7.2026 (4) Å	θ = 2.7–27.5°
b = 13.4736 (8) Å	µ = 1.89 mm⁻¹
c = 14.9785 (8) Å	T = 100 K
β = 93.792 (5)°	Prism, light brown
V = 1450.41 (14) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5542 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4916 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.060
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.7°, θ_min = 2.7°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→17
T_min = 0.558, T_max = 0.650	l = −19→19
15682 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.1375P)²] where P = (F_o² + 2F_c²)/3
5542 reflections	(Δ/σ)_max = 0.001
151 parameters	Δρ_max = 1.61 e Å⁻³
0 restraints	Δρ_min = −1.98 e Å⁻³

Crystal data top

[Sn(CH₃)₃(NCS)(C₇H₁₀N₂)]	V = 1450.41 (14) Å³
M_r = 344.04	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2026 (4) Å	µ = 1.89 mm⁻¹
b = 13.4736 (8) Å	T = 100 K
c = 14.9785 (8) Å	0.35 × 0.30 × 0.25 mm
β = 93.792 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5542 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	4916 reflections with I > 2σ(I)
T_min = 0.558, T_max = 0.650	R_int = 0.060
15682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.23	Δρ_max = 1.61 e Å⁻³
5542 reflections	Δρ_min = −1.98 e Å⁻³
151 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.25215 (5)	0.41625 (3)	0.86069 (2)	0.01334 (16)
S1	0.3130 (2)	0.35874 (10)	1.18988 (10)	0.0267 (4)
N1	0.2370 (6)	0.4769 (3)	0.7145 (3)	0.0145 (9)
N2	0.2613 (7)	0.5696 (3)	0.4491 (3)	0.0160 (10)
N3	0.2743 (7)	0.3468 (4)	1.0044 (3)	0.0298 (12)
C1	0.5262 (7)	0.3660 (4)	0.8426 (4)	0.0176 (11)
H1A	0.6000	0.4208	0.8204	0.026*
H1B	0.5216	0.3116	0.7991	0.026*
H1C	0.5835	0.3425	0.8999	0.026*
C2	0.0214 (8)	0.3222 (5)	0.8288 (4)	0.0247 (13)
H2A	−0.0670	0.3561	0.7866	0.037*
H2B	−0.0398	0.3060	0.8835	0.037*
H2C	0.0644	0.2609	0.8015	0.037*
C3	0.2037 (8)	0.5581 (4)	0.9169 (4)	0.0219 (12)
H3A	0.0925	0.5878	0.8865	0.033*
H3B	0.3113	0.6011	0.9092	0.033*
H3C	0.1851	0.5509	0.9807	0.033*
C4	0.2356 (7)	0.4114 (4)	0.6457 (3)	0.0146 (11)
H4	0.2297	0.3427	0.6592	0.018*
C5	0.2421 (8)	0.4383 (4)	0.5584 (4)	0.0151 (11)
H5	0.2408	0.3884	0.5135	0.018*
C6	0.2507 (7)	0.5397 (3)	0.5334 (3)	0.0118 (10)
C7	0.2515 (8)	0.6078 (4)	0.6063 (4)	0.0159 (11)
H7	0.2566	0.6771	0.5952	0.019*
C8	0.2448 (8)	0.5743 (3)	0.6913 (4)	0.0152 (11)
H8	0.2457	0.6221	0.7379	0.018*
C9	0.2689 (9)	0.6754 (4)	0.4273 (4)	0.0232 (12)
H9A	0.3785	0.7053	0.4590	0.035*
H9B	0.1563	0.7083	0.4458	0.035*
H9C	0.2771	0.6834	0.3627	0.035*
C10	0.2531 (8)	0.4977 (5)	0.3755 (4)	0.0224 (12)
H10A	0.3642	0.4556	0.3805	0.034*
H10B	0.2477	0.5331	0.3183	0.034*
H10C	0.1418	0.4563	0.3786	0.034*
C11	0.2906 (7)	0.3530 (4)	1.0821 (4)	0.0171 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0109 (2)	0.0157 (2)	0.0135 (2)	0.00108 (13)	0.00189 (17)	0.00061 (12)
S1	0.0435 (9)	0.0206 (7)	0.0158 (7)	−0.0071 (7)	−0.0002 (7)	−0.0019 (5)
N1	0.017 (2)	0.0109 (19)	0.015 (2)	0.0021 (17)	−0.0028 (19)	−0.0013 (16)
N2	0.020 (3)	0.014 (2)	0.014 (2)	−0.0016 (18)	0.001 (2)	0.0002 (16)
N3	0.031 (3)	0.042 (3)	0.017 (3)	0.004 (3)	0.009 (2)	0.003 (2)
C1	0.004 (2)	0.028 (3)	0.020 (3)	−0.003 (2)	−0.001 (2)	0.006 (2)
C2	0.014 (3)	0.030 (3)	0.030 (3)	−0.015 (2)	0.003 (2)	0.004 (3)
C3	0.021 (3)	0.024 (3)	0.022 (3)	0.002 (2)	0.008 (3)	−0.006 (2)
C4	0.016 (3)	0.011 (2)	0.017 (3)	0.0000 (18)	0.000 (3)	0.0000 (18)
C5	0.015 (3)	0.013 (2)	0.017 (3)	0.002 (2)	0.001 (2)	−0.0027 (19)
C6	0.006 (2)	0.013 (2)	0.016 (2)	−0.0007 (18)	0.001 (2)	−0.0023 (19)
C7	0.016 (3)	0.012 (2)	0.019 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C8	0.015 (3)	0.012 (2)	0.019 (3)	0.0017 (19)	0.000 (2)	−0.0031 (18)
C9	0.032 (3)	0.020 (3)	0.019 (3)	−0.003 (2)	0.008 (3)	0.004 (2)
C10	0.026 (3)	0.027 (3)	0.013 (2)	0.004 (2)	0.000 (2)	−0.001 (2)
C11	0.007 (2)	0.018 (2)	0.027 (3)	0.000 (2)	0.004 (2)	0.008 (2)

Geometric parameters (Å, º) top

Sn1—C2	2.120 (5)	C3—H3A	0.9800
Sn1—C1	2.121 (5)	C3—H3B	0.9800
Sn1—C3	2.126 (5)	C3—H3C	0.9800
Sn1—N1	2.333 (4)	C4—C5	1.360 (7)
Sn1—N3	2.344 (5)	C4—H4	0.9500
S1—C11	1.614 (6)	C5—C6	1.419 (6)
N1—C4	1.357 (6)	C5—H5	0.9500
N1—C8	1.359 (6)	C6—C7	1.426 (7)
N2—C6	1.333 (6)	C7—C8	1.354 (8)
N2—C9	1.464 (6)	C7—H7	0.9500
N2—C10	1.466 (7)	C8—H8	0.9500
N3—C11	1.164 (7)	C9—H9A	0.9800
C1—H1A	0.9800	C9—H9B	0.9800
C1—H1B	0.9800	C9—H9C	0.9800
C1—H1C	0.9800	C10—H10A	0.9800
C2—H2A	0.9800	C10—H10B	0.9800
C2—H2B	0.9800	C10—H10C	0.9800
C2—H2C	0.9800

C2—Sn1—C1	120.2 (2)	Sn1—C3—H3C	109.5
C2—Sn1—C3	118.7 (2)	H3A—C3—H3C	109.5
C1—Sn1—C3	121.1 (2)	H3B—C3—H3C	109.5
C2—Sn1—N1	90.6 (2)	N1—C4—C5	124.0 (4)
C1—Sn1—N1	88.74 (18)	N1—C4—H4	118.0
C3—Sn1—N1	93.30 (18)	C5—C4—H4	118.0
C2—Sn1—N3	88.5 (2)	C4—C5—C6	120.9 (5)
C1—Sn1—N3	89.0 (2)	C4—C5—H5	119.5
C3—Sn1—N3	89.9 (2)	C6—C5—H5	119.5
N1—Sn1—N3	176.70 (16)	N2—C6—C5	123.2 (4)
C4—N1—C8	115.5 (5)	N2—C6—C7	122.2 (5)
C4—N1—Sn1	118.9 (3)	C5—C6—C7	114.6 (5)
C8—N1—Sn1	125.4 (3)	C8—C7—C6	120.4 (5)
C6—N2—C9	120.7 (4)	C8—C7—H7	119.8
C6—N2—C10	120.7 (4)	C6—C7—H7	119.8
C9—N2—C10	118.4 (5)	C7—C8—N1	124.6 (5)
C11—N3—Sn1	152.3 (5)	C7—C8—H8	117.7
Sn1—C1—H1A	109.5	N1—C8—H8	117.7
Sn1—C1—H1B	109.5	N2—C9—H9A	109.5
H1A—C1—H1B	109.5	N2—C9—H9B	109.5
Sn1—C1—H1C	109.5	H9A—C9—H9B	109.5
H1A—C1—H1C	109.5	N2—C9—H9C	109.5
H1B—C1—H1C	109.5	H9A—C9—H9C	109.5
Sn1—C2—H2A	109.5	H9B—C9—H9C	109.5
Sn1—C2—H2B	109.5	N2—C10—H10A	109.5
H2A—C2—H2B	109.5	N2—C10—H10B	109.5
Sn1—C2—H2C	109.5	H10A—C10—H10B	109.5
H2A—C2—H2C	109.5	N2—C10—H10C	109.5
H2B—C2—H2C	109.5	H10A—C10—H10C	109.5
Sn1—C3—H3A	109.5	H10B—C10—H10C	109.5
Sn1—C3—H3B	109.5	N3—C11—S1	178.7 (5)
H3A—C3—H3B	109.5

C2—Sn1—N1—C4	−52.6 (4)	C9—N2—C6—C5	179.7 (5)
C1—Sn1—N1—C4	67.6 (4)	C10—N2—C6—C5	3.8 (8)
C3—Sn1—N1—C4	−171.4 (4)	C9—N2—C6—C7	−1.8 (8)
C2—Sn1—N1—C8	133.2 (5)	C10—N2—C6—C7	−177.7 (5)
C1—Sn1—N1—C8	−106.6 (5)	C4—C5—C6—N2	178.5 (5)
C3—Sn1—N1—C8	14.4 (5)	C4—C5—C6—C7	−0.1 (8)
C2—Sn1—N3—C11	−133.1 (10)	N2—C6—C7—C8	−178.4 (5)
C1—Sn1—N3—C11	106.7 (10)	C5—C6—C7—C8	0.2 (8)
C3—Sn1—N3—C11	−14.4 (10)	C6—C7—C8—N1	−0.1 (9)
C8—N1—C4—C5	0.3 (8)	C4—N1—C8—C7	−0.2 (8)
Sn1—N1—C4—C5	−174.5 (4)	Sn1—N1—C8—C7	174.2 (5)
N1—C4—C5—C6	−0.1 (9)

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(NCS)(C₇H₁₀N₂)]
M_r	344.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.2026 (4), 13.4736 (8), 14.9785 (8)
β (°)	93.792 (5)
V (Å³)	1450.41 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.558, 0.650
No. of measured, independent and observed [I > 2σ(I)] reflections	15682, 5542, 4916
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.197, 1.23
No. of reflections	5542
No. of parameters	151
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.61, −1.98

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

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