Dimeth­yl(4′-pyridyl-2,2′:6′,2′′-terpyridine-κ3N1,N1′,N1′′)bis(thio­cyanato-κN)tin(IV)

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

doi:10.1107/S1600536811001309

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m211

doi:10.1107/S1600536811001309

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Dimethyl(4′-pyridyl-2,2′:6′,2′′-terpyridine-κ³N¹,N^1′,N^1′′)bis(thiocyanato-κN)tin(IV)

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

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 9 January 2011; accepted 10 January 2011; online 15 January 2011)

The Sn atom in the title compound, [Sn(CH₃)₂(NCS)₂(C₂₀H₁₄N₄)], is N,N′,N′′-chelated by the terpyridine part of the N-heterocycle. The Sn atom exists in a trans-C₂SnN₅ pentagonal–bipyramidal geometry [C—Sn—C = 173.66 (8)°] with the methyl groups in axial and the N atoms in equatorial positions.

Related literature

For the dimethyltin dichloride–terpyridine adduct, see: Naik & Scheidt (1973 ).

Experimental

Crystal data

[Sn(CH₃)₂(NCS)₂(C₂₀H₁₄N₄)]
M_r = 575.27
Triclinic, $[P \overline 1]$
a = 9.3269 (3) Å
b = 10.5017 (3) Å
c = 13.1503 (4) Å
α = 66.814 (3)°
β = 87.665 (3)°
γ = 83.552 (2)°
V = 1176.52 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.10 mm

Data collection

Agilent Technologies SuperNova diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ) T_min = 0.783, T_max = 0.882
15704 measured reflections
5168 independent reflections
4728 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.060
S = 1.04
5168 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: CrysAlis PRO (Agilent Technologies, 2010); 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/S1600536811001309/bt5461sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001309/bt5461Isup2.hkl

checkCIF report

Comment top

Diorganotin dihalides/pseudohalides form a number of adducts with terpyridine and its derivatives. The dimethyltin diisocyanate forms an adduct with terpyridine itself (Naik & Scheidt, 1973); the ligand chelates to the tin atom through its three N atoms. The 4'-pyridylterpyridine has a similar seven-coordinate structure (Scheme I, Fig. 1). It also features the chelated tin atom in a seven-coordinate geometry.

Related literature top

For the dimethyltin dichloride–terpyridine adduct, see: Naik & Scheidt (1973).

Experimental top

Dimethyltin diisothiocyanate and 4'-pyridyl-2,2':6',2"-terpyridine (1 mmol) were loaded into a convection tube. The tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell refinement: CrysAlis PRO (Agilent Technologies, 2010); data reduction: CrysAlis PRO (Agilent Technologies, 2010); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of diisothiocyanatodimethyl(4'-pyridylterpyridine)tin at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Dimethyl(4'-pyridyl-2,2':6',2''-terpyridine- κ³N¹,N^1',N^1'')bis(thiocyanato-κN)tin(IV) top

Crystal data top

[Sn(CH₃)₂(NCS)₂(C₂₀H₁₄N₄)]	Z = 2
M_r = 575.27	F(000) = 576
Triclinic, P1	D_x = 1.624 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3269 (3) Å	Cell parameters from 10240 reflections
b = 10.5017 (3) Å	θ = 2.2–29.4°
c = 13.1503 (4) Å	µ = 1.29 mm⁻¹
α = 66.814 (3)°	T = 100 K
β = 87.665 (3)°	Prism, colorless
γ = 83.552 (2)°	0.20 × 0.20 × 0.10 mm
V = 1176.52 (6) Å³

Data collection top

Agilent Technologies SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector	5168 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4728 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −13→13
T_min = 0.783, T_max = 0.882	l = −17→16
15704 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.027P)² + 0.2766P] where P = (F_o² + 2F_c²)/3
5168 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn(CH₃)₂(NCS)₂(C₂₀H₁₄N₄)]	γ = 83.552 (2)°
M_r = 575.27	V = 1176.52 (6) Å³
Triclinic, P1	Z = 2
a = 9.3269 (3) Å	Mo Kα radiation
b = 10.5017 (3) Å	µ = 1.29 mm⁻¹
c = 13.1503 (4) Å	T = 100 K
α = 66.814 (3)°	0.20 × 0.20 × 0.10 mm
β = 87.665 (3)°

Data collection top

Agilent Technologies SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector	5168 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	4728 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.882	R_int = 0.028
15704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 1.04	Δρ_max = 0.51 e Å⁻³
5168 reflections	Δρ_min = −0.49 e Å⁻³
300 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.670329 (15)	0.378196 (13)	0.343774 (11)	0.01570 (6)
S1	0.14249 (6)	0.55757 (6)	0.27483 (5)	0.02139 (12)
S2	0.54381 (7)	0.07411 (6)	0.72375 (5)	0.02716 (14)
N1	0.65080 (18)	0.52567 (17)	0.13746 (14)	0.0154 (4)
N2	0.88281 (18)	0.34503 (16)	0.22361 (14)	0.0137 (4)
N3	0.90522 (19)	0.26172 (17)	0.44304 (14)	0.0166 (4)
N4	1.26459 (19)	−0.03774 (18)	−0.05850 (15)	0.0184 (4)
N5	0.4323 (2)	0.45490 (19)	0.32114 (15)	0.0241 (4)
N6	0.5991 (2)	0.2807 (2)	0.51867 (15)	0.0256 (4)
C1	0.6332 (2)	0.1957 (2)	0.3225 (2)	0.0232 (5)
H1A	0.6343	0.2139	0.2434	0.035*
H1B	0.5391	0.1673	0.3536	0.035*
H1C	0.7091	0.1210	0.3606	0.035*
C2	0.7301 (2)	0.5579 (2)	0.35758 (18)	0.0201 (5)
H2A	0.7350	0.5426	0.4359	0.030*
H2B	0.6583	0.6369	0.3198	0.030*
H2C	0.8247	0.5779	0.3235	0.030*
C3	0.5515 (2)	0.6360 (2)	0.09447 (18)	0.0183 (4)
H3	0.4899	0.6621	0.1439	0.022*
C4	0.5342 (2)	0.7135 (2)	−0.01779 (18)	0.0200 (5)
H4	0.4632	0.7915	−0.0447	0.024*
C5	0.6229 (2)	0.6748 (2)	−0.08986 (17)	0.0185 (4)
H5	0.6121	0.7244	−0.1675	0.022*
C6	0.7274 (2)	0.5631 (2)	−0.04746 (17)	0.0166 (4)
H6	0.7900	0.5355	−0.0956	0.020*
C7	0.7396 (2)	0.4917 (2)	0.06618 (17)	0.0142 (4)
C8	0.8551 (2)	0.3767 (2)	0.11653 (17)	0.0138 (4)
C9	0.9287 (2)	0.3065 (2)	0.05728 (17)	0.0152 (4)
H9	0.9077	0.3327	−0.0188	0.018*
C10	1.0339 (2)	0.1968 (2)	0.11041 (17)	0.0146 (4)
C11	1.0643 (2)	0.1662 (2)	0.22092 (17)	0.0155 (4)
H11	1.1366	0.0935	0.2594	0.019*
C12	0.9879 (2)	0.2429 (2)	0.27423 (17)	0.0142 (4)
C13	1.0163 (2)	0.2199 (2)	0.39065 (17)	0.0158 (4)
C14	1.1508 (2)	0.1658 (2)	0.43977 (18)	0.0186 (5)
H14	1.2260	0.1346	0.4015	0.022*
C15	1.1733 (2)	0.1583 (2)	0.54597 (18)	0.0206 (5)
H15	1.2647	0.1238	0.5811	0.025*
C16	1.0606 (2)	0.2018 (2)	0.59894 (18)	0.0214 (5)
H16	1.0731	0.1974	0.6716	0.026*
C17	0.9282 (2)	0.2523 (2)	0.54579 (18)	0.0202 (5)
H17	0.8509	0.2813	0.5837	0.024*
C18	1.1117 (2)	0.1161 (2)	0.05122 (17)	0.0148 (4)
C19	1.1493 (2)	0.1789 (2)	−0.05975 (17)	0.0165 (4)
H19	1.1225	0.2753	−0.1005	0.020*
C20	1.2262 (2)	0.0990 (2)	−0.11010 (17)	0.0172 (4)
H20	1.2531	0.1439	−0.1853	0.021*
C21	1.2265 (2)	−0.0968 (2)	0.04727 (18)	0.0176 (4)
H21	1.2523	−0.1940	0.0853	0.021*
C22	1.1520 (2)	−0.0258 (2)	0.10523 (17)	0.0156 (4)
H22	1.1286	−0.0733	0.1809	0.019*
C23	0.3116 (2)	0.4974 (2)	0.30293 (17)	0.0173 (4)
C24	0.5756 (2)	0.1937 (2)	0.60383 (18)	0.0198 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01512 (9)	0.01554 (8)	0.01612 (9)	−0.00096 (6)	0.00146 (6)	−0.00616 (6)
S1	0.0158 (3)	0.0253 (3)	0.0245 (3)	0.0018 (2)	0.0006 (2)	−0.0123 (2)
S2	0.0260 (3)	0.0268 (3)	0.0212 (3)	−0.0053 (2)	0.0007 (3)	−0.0008 (2)
N1	0.0135 (9)	0.0140 (8)	0.0186 (9)	−0.0003 (7)	0.0013 (7)	−0.0068 (7)
N2	0.0137 (8)	0.0124 (8)	0.0152 (9)	0.0003 (7)	−0.0017 (7)	−0.0059 (7)
N3	0.0198 (9)	0.0161 (9)	0.0148 (9)	−0.0019 (7)	0.0007 (8)	−0.0069 (7)
N4	0.0171 (9)	0.0202 (9)	0.0200 (10)	0.0007 (7)	0.0010 (8)	−0.0107 (8)
N5	0.0177 (10)	0.0272 (10)	0.0232 (10)	0.0003 (8)	0.0035 (8)	−0.0065 (8)
N6	0.0252 (11)	0.0283 (10)	0.0178 (10)	−0.0040 (8)	0.0061 (9)	−0.0034 (8)
C1	0.0242 (12)	0.0159 (10)	0.0304 (13)	−0.0034 (9)	−0.0040 (10)	−0.0091 (10)
C2	0.0256 (12)	0.0136 (10)	0.0220 (12)	−0.0013 (9)	0.0013 (10)	−0.0082 (9)
C3	0.0154 (11)	0.0178 (10)	0.0224 (12)	0.0005 (8)	0.0033 (9)	−0.0096 (9)
C4	0.0172 (11)	0.0154 (10)	0.0244 (12)	0.0043 (9)	−0.0036 (10)	−0.0057 (9)
C5	0.0198 (11)	0.0189 (10)	0.0141 (11)	0.0002 (9)	−0.0040 (9)	−0.0040 (9)
C6	0.0170 (11)	0.0184 (10)	0.0166 (11)	−0.0009 (8)	−0.0001 (9)	−0.0094 (9)
C7	0.0133 (10)	0.0127 (9)	0.0185 (11)	−0.0009 (8)	−0.0019 (9)	−0.0081 (8)
C8	0.0125 (10)	0.0120 (9)	0.0164 (10)	−0.0012 (8)	−0.0001 (8)	−0.0049 (8)
C9	0.0155 (10)	0.0155 (10)	0.0148 (10)	−0.0016 (8)	0.0002 (9)	−0.0064 (8)
C10	0.0133 (10)	0.0142 (9)	0.0177 (11)	−0.0030 (8)	0.0028 (9)	−0.0076 (8)
C11	0.0141 (10)	0.0130 (9)	0.0174 (11)	0.0004 (8)	0.0003 (9)	−0.0041 (8)
C12	0.0124 (10)	0.0153 (10)	0.0151 (10)	−0.0014 (8)	0.0003 (8)	−0.0062 (8)
C13	0.0182 (11)	0.0111 (9)	0.0171 (11)	−0.0009 (8)	0.0005 (9)	−0.0046 (8)
C14	0.0173 (11)	0.0178 (10)	0.0199 (11)	0.0039 (9)	−0.0038 (9)	−0.0078 (9)
C15	0.0208 (11)	0.0162 (10)	0.0226 (12)	0.0007 (9)	−0.0102 (10)	−0.0049 (9)
C16	0.0287 (12)	0.0208 (11)	0.0155 (11)	−0.0032 (10)	−0.0044 (10)	−0.0075 (9)
C17	0.0230 (12)	0.0212 (11)	0.0181 (11)	−0.0026 (9)	0.0011 (10)	−0.0095 (9)
C18	0.0120 (10)	0.0163 (10)	0.0186 (11)	−0.0013 (8)	0.0001 (9)	−0.0097 (9)
C19	0.0156 (10)	0.0154 (10)	0.0179 (11)	0.0001 (8)	−0.0007 (9)	−0.0063 (8)
C20	0.0160 (11)	0.0203 (10)	0.0147 (11)	−0.0020 (9)	0.0011 (9)	−0.0063 (9)
C21	0.0153 (10)	0.0146 (10)	0.0224 (12)	0.0014 (8)	−0.0006 (9)	−0.0075 (9)
C22	0.0133 (10)	0.0172 (10)	0.0154 (10)	−0.0006 (8)	0.0007 (9)	−0.0057 (8)
C23	0.0216 (12)	0.0164 (10)	0.0131 (10)	−0.0041 (9)	0.0058 (9)	−0.0050 (8)
C24	0.0131 (10)	0.0261 (11)	0.0228 (12)	0.0001 (9)	−0.0008 (9)	−0.0129 (10)

Geometric parameters (Å, º) top

Sn1—C2	2.102 (2)	C5—C6	1.382 (3)
Sn1—C1	2.110 (2)	C5—H5	0.9500
Sn1—N6	2.2258 (18)	C6—C7	1.386 (3)
Sn1—N5	2.2645 (19)	C6—H6	0.9500
Sn1—N3	2.5246 (17)	C7—C8	1.481 (3)
Sn1—N1	2.5418 (17)	C8—C9	1.385 (3)
Sn1—N2	2.5630 (17)	C9—C10	1.395 (3)
S1—C23	1.632 (2)	C9—H9	0.9500
S2—C24	1.624 (2)	C10—C11	1.393 (3)
N1—C3	1.343 (3)	C10—C18	1.478 (3)
N1—C7	1.351 (3)	C11—C12	1.387 (3)
N2—C8	1.342 (3)	C11—H11	0.9500
N2—C12	1.345 (3)	C12—C13	1.483 (3)
N3—C17	1.340 (3)	C13—C14	1.389 (3)
N3—C13	1.349 (3)	C14—C15	1.391 (3)
N4—C21	1.332 (3)	C14—H14	0.9500
N4—C20	1.337 (3)	C15—C16	1.372 (3)
N5—C23	1.161 (3)	C15—H15	0.9500
N6—C24	1.164 (3)	C16—C17	1.388 (3)
C1—H1A	0.9800	C16—H16	0.9500
C1—H1B	0.9800	C17—H17	0.9500
C1—H1C	0.9800	C18—C22	1.389 (3)
C2—H2A	0.9800	C18—C19	1.393 (3)
C2—H2B	0.9800	C19—C20	1.385 (3)
C2—H2C	0.9800	C19—H19	0.9500
C3—C4	1.383 (3)	C20—H20	0.9500
C3—H3	0.9500	C21—C22	1.382 (3)
C4—C5	1.383 (3)	C21—H21	0.9500
C4—H4	0.9500	C22—H22	0.9500

C2—Sn1—C1	173.66 (8)	C7—C6—C5	119.20 (19)
C2—Sn1—N6	95.00 (8)	C7—C6—H6	120.4
C1—Sn1—N6	88.97 (8)	C5—C6—H6	120.4
C2—Sn1—N5	94.55 (8)	N1—C7—C6	122.26 (18)
C1—Sn1—N5	90.97 (8)	N1—C7—C8	116.12 (18)
N6—Sn1—N5	80.75 (7)	C6—C7—C8	121.57 (18)
C2—Sn1—N3	84.97 (7)	N2—C8—C9	122.46 (18)
C1—Sn1—N3	91.04 (7)	N2—C8—C7	115.30 (17)
N6—Sn1—N3	77.94 (6)	C9—C8—C7	122.25 (18)
N5—Sn1—N3	158.55 (6)	C8—C9—C10	119.37 (19)
C2—Sn1—N1	85.50 (7)	C8—C9—H9	120.3
C1—Sn1—N1	92.67 (7)	C10—C9—H9	120.3
N6—Sn1—N1	158.04 (6)	C11—C10—C9	117.91 (18)
N5—Sn1—N1	77.33 (6)	C11—C10—C18	120.97 (18)
N3—Sn1—N1	123.89 (5)	C9—C10—C18	121.12 (19)
C2—Sn1—N2	97.06 (7)	C12—C11—C10	119.39 (19)
C1—Sn1—N2	76.72 (7)	C12—C11—H11	120.3
N6—Sn1—N2	138.11 (6)	C10—C11—H11	120.3
N5—Sn1—N2	137.58 (6)	N2—C12—C11	122.32 (19)
N3—Sn1—N2	63.44 (5)	N2—C12—C13	114.86 (17)
N1—Sn1—N2	63.18 (5)	C11—C12—C13	122.81 (18)
C3—N1—C7	117.48 (17)	N3—C13—C14	122.62 (19)
C3—N1—Sn1	122.53 (13)	N3—C13—C12	115.37 (18)
C7—N1—Sn1	119.96 (12)	C14—C13—C12	121.93 (19)
C8—N2—C12	118.48 (17)	C15—C14—C13	118.8 (2)
C8—N2—Sn1	117.17 (13)	C15—C14—H14	120.6
C12—N2—Sn1	116.78 (13)	C13—C14—H14	120.6
C17—N3—C13	117.84 (18)	C16—C15—C14	118.5 (2)
C17—N3—Sn1	120.77 (14)	C16—C15—H15	120.7
C13—N3—Sn1	121.07 (13)	C14—C15—H15	120.7
C21—N4—C20	116.62 (17)	C15—C16—C17	119.7 (2)
C23—N5—Sn1	176.01 (17)	C15—C16—H16	120.2
C24—N6—Sn1	159.06 (18)	C17—C16—H16	120.2
Sn1—C1—H1A	109.5	N3—C17—C16	122.5 (2)
Sn1—C1—H1B	109.5	N3—C17—H17	118.7
H1A—C1—H1B	109.5	C16—C17—H17	118.7
Sn1—C1—H1C	109.5	C22—C18—C19	117.38 (18)
H1A—C1—H1C	109.5	C22—C18—C10	120.88 (18)
H1B—C1—H1C	109.5	C19—C18—C10	121.73 (18)
Sn1—C2—H2A	109.5	C20—C19—C18	119.26 (19)
Sn1—C2—H2B	109.5	C20—C19—H19	120.4
H2A—C2—H2B	109.5	C18—C19—H19	120.4
Sn1—C2—H2C	109.5	N4—C20—C19	123.52 (19)
H2A—C2—H2C	109.5	N4—C20—H20	118.2
H2B—C2—H2C	109.5	C19—C20—H20	118.2
N1—C3—C4	123.57 (19)	N4—C21—C22	124.19 (19)
N1—C3—H3	118.2	N4—C21—H21	117.9
C4—C3—H3	118.2	C22—C21—H21	117.9
C3—C4—C5	118.28 (19)	C21—C22—C18	119.01 (19)
C3—C4—H4	120.9	C21—C22—H22	120.5
C5—C4—H4	120.9	C18—C22—H22	120.5
C6—C5—C4	119.17 (19)	N5—C23—S1	178.9 (2)
C6—C5—H5	120.4	N6—C24—S2	178.9 (2)
C4—C5—H5	120.4

C2—Sn1—N1—C3	−65.95 (16)	Sn1—N1—C7—C8	−6.5 (2)
C1—Sn1—N1—C3	120.14 (17)	C5—C6—C7—N1	1.4 (3)
N6—Sn1—N1—C3	26.3 (3)	C5—C6—C7—C8	−176.24 (19)
N5—Sn1—N1—C3	29.74 (16)	C12—N2—C8—C9	1.2 (3)
N3—Sn1—N1—C3	−146.81 (15)	Sn1—N2—C8—C9	−147.48 (16)
N2—Sn1—N1—C3	−166.20 (17)	C12—N2—C8—C7	−179.06 (17)
C2—Sn1—N1—C7	116.06 (16)	Sn1—N2—C8—C7	32.2 (2)
C1—Sn1—N1—C7	−57.86 (16)	N1—C7—C8—N2	−17.1 (3)
N6—Sn1—N1—C7	−151.74 (18)	C6—C7—C8—N2	160.63 (18)
N5—Sn1—N1—C7	−148.25 (16)	N1—C7—C8—C9	162.59 (18)
N3—Sn1—N1—C7	35.19 (16)	C6—C7—C8—C9	−19.7 (3)
N2—Sn1—N1—C7	15.81 (13)	N2—C8—C9—C10	1.2 (3)
C2—Sn1—N2—C8	−106.42 (14)	C7—C8—C9—C10	−178.43 (18)
C1—Sn1—N2—C8	74.85 (14)	C8—C9—C10—C11	−2.5 (3)
N6—Sn1—N2—C8	147.95 (14)	C8—C9—C10—C18	177.98 (18)
N5—Sn1—N2—C8	−1.71 (18)	C9—C10—C11—C12	1.3 (3)
N3—Sn1—N2—C8	172.83 (15)	C18—C10—C11—C12	−179.16 (18)
N1—Sn1—N2—C8	−25.11 (13)	C8—N2—C12—C11	−2.5 (3)
C2—Sn1—N2—C12	104.32 (15)	Sn1—N2—C12—C11	146.34 (16)
C1—Sn1—N2—C12	−74.41 (15)	C8—N2—C12—C13	176.96 (17)
N6—Sn1—N2—C12	−1.31 (19)	Sn1—N2—C12—C13	−34.2 (2)
N5—Sn1—N2—C12	−150.97 (14)	C10—C11—C12—N2	1.2 (3)
N3—Sn1—N2—C12	23.57 (13)	C10—C11—C12—C13	−178.18 (18)
N1—Sn1—N2—C12	−174.37 (16)	C17—N3—C13—C14	1.2 (3)
C2—Sn1—N3—C17	62.31 (16)	Sn1—N3—C13—C14	174.64 (15)
C1—Sn1—N3—C17	−122.63 (16)	C17—N3—C13—C12	−175.43 (18)
N6—Sn1—N3—C17	−33.91 (16)	Sn1—N3—C13—C12	−2.0 (2)
N5—Sn1—N3—C17	−27.3 (3)	N2—C12—C13—N3	24.1 (3)
N1—Sn1—N3—C17	143.45 (14)	C11—C12—C13—N3	−156.48 (19)
N2—Sn1—N3—C17	162.79 (17)	N2—C12—C13—C14	−152.59 (19)
C2—Sn1—N3—C13	−110.95 (16)	C11—C12—C13—C14	26.9 (3)
C1—Sn1—N3—C13	64.12 (16)	N3—C13—C14—C15	−2.0 (3)
N6—Sn1—N3—C13	152.84 (16)	C12—C13—C14—C15	174.45 (19)
N5—Sn1—N3—C13	159.42 (17)	C13—C14—C15—C16	1.4 (3)
N1—Sn1—N3—C13	−29.80 (17)	C14—C15—C16—C17	−0.2 (3)
N2—Sn1—N3—C13	−10.47 (14)	C13—N3—C17—C16	0.1 (3)
C2—Sn1—N6—C24	−150.2 (5)	Sn1—N3—C17—C16	−173.39 (15)
C1—Sn1—N6—C24	24.8 (5)	C15—C16—C17—N3	−0.5 (3)
N5—Sn1—N6—C24	116.0 (5)	C11—C10—C18—C22	35.8 (3)
N3—Sn1—N6—C24	−66.5 (5)	C9—C10—C18—C22	−144.7 (2)
N1—Sn1—N6—C24	119.4 (5)	C11—C10—C18—C19	−143.3 (2)
N2—Sn1—N6—C24	−43.8 (5)	C9—C10—C18—C19	36.3 (3)
C7—N1—C3—C4	1.3 (3)	C22—C18—C19—C20	−1.2 (3)
Sn1—N1—C3—C4	−176.70 (15)	C10—C18—C19—C20	177.93 (19)
N1—C3—C4—C5	0.7 (3)	C21—N4—C20—C19	−0.7 (3)
C3—C4—C5—C6	−1.7 (3)	C18—C19—C20—N4	1.5 (3)
C4—C5—C6—C7	0.7 (3)	C20—N4—C21—C22	−0.4 (3)
C3—N1—C7—C6	−2.4 (3)	N4—C21—C22—C18	0.7 (3)
Sn1—N1—C7—C6	175.74 (15)	C19—C18—C22—C21	0.1 (3)
C3—N1—C7—C8	175.36 (18)	C10—C18—C22—C21	−178.98 (19)

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(NCS)₂(C₂₀H₁₄N₄)]
M_r	575.27
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3269 (3), 10.5017 (3), 13.1503 (4)
α, β, γ (°)	66.814 (3), 87.665 (3), 83.552 (2)
V (Å³)	1176.52 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Agilent Technologies SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent Technologies, 2010)
T_min, T_max	0.783, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	15704, 5168, 4728
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.060, 1.04
No. of reflections	5168
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.49

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

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Agilent Technologies (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Naik, D. N. & Scheidt, W. R. (1973). Inorg. Chem. 12, 272–276. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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