Di-n-butyl­bis­(thio­cyanato-κN)(1,10-phenanthroline-κ2N,N′)tin(IV)

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

doi:10.1107/S1600536811001292

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m210

doi:10.1107/S1600536811001292

Open

access

Di-n-butylbis(thiocyanato-κN)(1,10-phenanthroline-κ²N,N′)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)

In the asymmetric unit of the title compound, [Sn(C₄H₉)₂(NCS)₂(C₁₂H₈N₂)], there are two independent molecules, both lying on a twofold rotation axis. The axis passes through the mid-point of the 1,10 and 5,6 bonds of the N-heterocycle and through the Sn atom. The Sn atoms show a slightly distorted SnC₂N₄ octahedral coordination.

Related literature

For the di-n-butyltin dichloride adduct, see: Ganis et al. (1983 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(NCS)₂(C₁₂H₈N₂]
M_r = 529.28
Monoclinic, P 2/n
a = 15.0008 (3) Å
b = 10.5220 (2) Å
c = 15.8359 (3) Å
β = 107.452 (2)°
V = 2384.46 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 100 K
0.30 × 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 = 0.703, T_max = 0.884
11981 measured reflections
5323 independent reflections
4659 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 1.02
5323 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.61 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/S1600536811001292/bt5460sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001292/bt5460Isup2.hkl

checkCIF report

Comment top

Diorganotin dihalides/pseudohalides form a number of adducts with 1,10-phenanthroline. The dihalides adducts have been better studied, particularly with dibutyltin dihalides adducts; the di-n-butyltin dichloride adduct was reported a long time ago (Ganis et al., 1983). The diisothiocyanate adduct (Scheme I, Fig. 1 & 2), also features the chelated tin atom in an octahedral geometry. The two independent molecules both lie on a twofold rotation axis; the axis passes through the mid-point of the 1,10 and 5,6 pairs of atoms of the N-heterocycle, and it relates one butyl group to the other (as well as one isothiocyanate group to the other).

Related literature top

For the di-n-butyltin dichloride adduct, see: Ganis et al. (1983).

Experimental top

Dibutyltin diisothiocyanate and 1,10-phenanthroline (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 the two independent molecules of dibutyldiisothiocyanato(1,10-phenanthroline)tin at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Di-n-butylbis(thiocyanato-κN)(1,10-phenanthroline- κ²N,N')tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(NCS)₂(C₁₂H₈N₂]	F(000) = 1072
M_r = 529.28	D_x = 1.474 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 10240 reflections
a = 15.0008 (3) Å	θ = 2.2–29.4°
b = 10.5220 (2) Å	µ = 1.26 mm⁻¹
c = 15.8359 (3) Å	T = 100 K
β = 107.452 (2)°	Prism, colorless
V = 2384.46 (8) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Agilent Technologies SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector	5323 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4659 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −19→18
Absorption correction: multi-scan CrysAlis PRO (Agilent Technologies, 2010)	k = −13→13
T_min = 0.703, T_max = 0.884	l = −13→20
11981 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0326P)² + 0.2915P] where P = (F_o² + 2F_c²)/3
5323 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(NCS)₂(C₁₂H₈N₂]	V = 2384.46 (8) Å³
M_r = 529.28	Z = 4
Monoclinic, P2/n	Mo Kα radiation
a = 15.0008 (3) Å	µ = 1.26 mm⁻¹
b = 10.5220 (2) Å	T = 100 K
c = 15.8359 (3) Å	0.30 × 0.20 × 0.10 mm
β = 107.452 (2)°

Data collection top

Agilent Technologies SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector	5323 independent reflections
Absorption correction: multi-scan CrysAlis PRO (Agilent Technologies, 2010)	4659 reflections with I > 2σ(I)
T_min = 0.703, T_max = 0.884	R_int = 0.029
11981 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
5323 reflections	Δρ_min = −0.61 e Å⁻³
263 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.7500	0.646740 (19)	0.2500	0.01691 (7)
Sn2	0.7500	0.61402 (2)	0.7500	0.01760 (7)
S1	0.80427 (5)	0.90208 (6)	0.00369 (4)	0.02442 (15)
S2	1.01982 (5)	0.34705 (6)	0.92845 (5)	0.02964 (16)
N1	0.76659 (13)	0.46325 (17)	0.16982 (12)	0.0186 (4)
N2	0.76347 (15)	0.7767 (2)	0.14184 (14)	0.0296 (5)
N3	0.83931 (12)	0.79303 (17)	0.80419 (12)	0.0168 (4)
N4	0.87303 (16)	0.4872 (2)	0.82567 (14)	0.0328 (5)
C1	0.60205 (16)	0.6504 (2)	0.19698 (17)	0.0232 (5)
H1A	0.5832	0.5919	0.1457	0.028*
H1B	0.5745	0.6180	0.2423	0.028*
C2	0.56148 (17)	0.7817 (2)	0.16729 (18)	0.0291 (6)
H2A	0.5763	0.8055	0.1125	0.035*
H2B	0.5917	0.8446	0.2135	0.035*
C3	0.45576 (19)	0.7876 (3)	0.14991 (18)	0.0394 (7)
H3A	0.4255	0.7214	0.1063	0.047*
H3B	0.4409	0.7696	0.2056	0.047*
C4	0.4165 (2)	0.9175 (3)	0.1149 (2)	0.0578 (10)
H4A	0.3488	0.9181	0.1049	0.087*
H4B	0.4297	0.9346	0.0590	0.087*
H4C	0.4458	0.9831	0.1582	0.087*
C5	0.78497 (16)	0.4644 (2)	0.09300 (15)	0.0238 (5)
H5	0.7912	0.5440	0.0670	0.029*
C6	0.79562 (19)	0.3532 (2)	0.04866 (17)	0.0292 (6)
H6	0.8094	0.3574	−0.0060	0.035*
C7	0.78590 (17)	0.2385 (2)	0.08520 (17)	0.0303 (6)
H7	0.7913	0.1621	0.0551	0.036*
C8	0.76801 (16)	0.2333 (2)	0.16709 (17)	0.0246 (6)
C9	0.75910 (15)	0.3498 (2)	0.20787 (15)	0.0184 (5)
C10	0.7587 (2)	0.1170 (2)	0.21069 (19)	0.0354 (7)
H10	0.7649	0.0383	0.1836	0.042*
C11	0.78116 (16)	0.8286 (2)	0.08429 (15)	0.0191 (5)
C12	0.70141 (16)	0.5978 (2)	0.86263 (15)	0.0207 (5)
H12A	0.6957	0.5064	0.8749	0.025*
H12B	0.7494	0.6343	0.9142	0.025*
C13	0.60877 (17)	0.6616 (2)	0.85540 (16)	0.0245 (5)
H13A	0.5619	0.6324	0.8004	0.029*
H13B	0.6162	0.7545	0.8505	0.029*
C14	0.57178 (19)	0.6351 (2)	0.93319 (17)	0.0289 (6)
H14A	0.5663	0.5421	0.9397	0.035*
H14B	0.6171	0.6675	0.9881	0.035*
C15	0.47828 (19)	0.6955 (3)	0.92244 (19)	0.0389 (7)
H15A	0.4576	0.6755	0.9740	0.058*
H15B	0.4327	0.6626	0.8688	0.058*
H15C	0.4836	0.7879	0.9175	0.058*
C16	0.92697 (16)	0.7912 (2)	0.85792 (15)	0.0217 (5)
H16	0.9561	0.7116	0.8764	0.026*
C17	0.97730 (18)	0.9027 (2)	0.88790 (16)	0.0262 (6)
H17	1.0397	0.8983	0.9260	0.031*
C18	0.93621 (17)	1.0177 (2)	0.86206 (16)	0.0262 (6)
H18	0.9701	1.0939	0.8815	0.031*
C19	0.84303 (17)	1.0231 (2)	0.80631 (16)	0.0224 (5)
C20	0.79742 (15)	0.9072 (2)	0.77864 (14)	0.0170 (5)
C21	0.79440 (18)	1.1396 (2)	0.77720 (18)	0.0282 (6)
H21	0.8249	1.2182	0.7964	0.034*
C22	0.93256 (18)	0.4328 (2)	0.86806 (16)	0.0214 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01948 (13)	0.01283 (11)	0.01867 (12)	0.000	0.00609 (9)	0.000
Sn2	0.01997 (13)	0.01451 (12)	0.01626 (12)	0.000	0.00229 (9)	0.000
S1	0.0332 (4)	0.0204 (3)	0.0224 (3)	0.0006 (3)	0.0125 (3)	0.0011 (2)
S2	0.0255 (3)	0.0243 (3)	0.0335 (4)	0.0060 (3)	0.0005 (3)	0.0004 (3)
N1	0.0181 (10)	0.0161 (9)	0.0203 (10)	0.0001 (8)	0.0039 (8)	−0.0006 (8)
N2	0.0296 (12)	0.0284 (11)	0.0316 (12)	0.0009 (10)	0.0105 (10)	0.0061 (10)
N3	0.0178 (9)	0.0175 (9)	0.0155 (9)	0.0000 (8)	0.0056 (8)	−0.0003 (8)
N4	0.0346 (13)	0.0373 (13)	0.0237 (11)	0.0053 (11)	0.0043 (10)	0.0009 (10)
C1	0.0183 (12)	0.0224 (12)	0.0282 (13)	0.0032 (10)	0.0058 (10)	−0.0001 (10)
C2	0.0286 (14)	0.0261 (13)	0.0307 (14)	0.0108 (11)	0.0062 (12)	0.0040 (11)
C3	0.0334 (15)	0.0569 (19)	0.0293 (15)	0.0216 (14)	0.0117 (12)	0.0055 (14)
C4	0.059 (2)	0.075 (2)	0.0418 (19)	0.044 (2)	0.0178 (17)	0.0180 (18)
C5	0.0262 (13)	0.0254 (12)	0.0188 (12)	0.0032 (11)	0.0052 (10)	0.0015 (10)
C6	0.0326 (14)	0.0309 (14)	0.0253 (14)	0.0074 (12)	0.0104 (12)	−0.0034 (11)
C7	0.0290 (14)	0.0266 (13)	0.0341 (15)	0.0083 (11)	0.0076 (12)	−0.0107 (12)
C8	0.0229 (12)	0.0172 (11)	0.0320 (14)	0.0025 (10)	0.0055 (11)	−0.0055 (10)
C9	0.0123 (11)	0.0167 (11)	0.0246 (13)	−0.0002 (9)	0.0030 (10)	−0.0002 (9)
C10	0.0415 (17)	0.0161 (11)	0.0488 (18)	0.0020 (12)	0.0139 (15)	−0.0046 (12)
C11	0.0187 (12)	0.0148 (10)	0.0220 (12)	0.0013 (9)	0.0035 (10)	−0.0045 (10)
C12	0.0234 (12)	0.0228 (12)	0.0154 (11)	−0.0037 (10)	0.0050 (10)	0.0027 (10)
C13	0.0246 (13)	0.0272 (13)	0.0211 (12)	−0.0022 (11)	0.0060 (11)	0.0017 (10)
C14	0.0300 (14)	0.0351 (14)	0.0216 (13)	−0.0056 (12)	0.0078 (11)	−0.0002 (11)
C15	0.0296 (15)	0.0591 (19)	0.0305 (15)	−0.0067 (14)	0.0128 (12)	−0.0019 (14)
C16	0.0209 (12)	0.0244 (12)	0.0193 (12)	0.0000 (10)	0.0054 (10)	−0.0028 (10)
C17	0.0213 (12)	0.0344 (14)	0.0218 (13)	−0.0055 (11)	0.0050 (10)	−0.0078 (11)
C18	0.0286 (13)	0.0237 (12)	0.0307 (14)	−0.0119 (11)	0.0154 (11)	−0.0097 (11)
C19	0.0265 (13)	0.0209 (11)	0.0248 (12)	−0.0033 (10)	0.0151 (11)	−0.0025 (10)
C20	0.0206 (12)	0.0162 (11)	0.0167 (11)	−0.0008 (9)	0.0092 (10)	−0.0022 (9)
C21	0.0358 (15)	0.0170 (11)	0.0386 (16)	−0.0042 (10)	0.0217 (13)	−0.0037 (10)
C22	0.0305 (14)	0.0147 (11)	0.0240 (13)	−0.0035 (11)	0.0157 (11)	−0.0056 (10)

Geometric parameters (Å, º) top

Sn1—C1ⁱ	2.125 (2)	C5—H5	0.9500
Sn1—C1	2.125 (2)	C6—C7	1.365 (4)
Sn1—N2ⁱ	2.248 (2)	C6—H6	0.9500
Sn1—N2	2.248 (2)	C7—C8	1.402 (4)
Sn1—N1	2.3646 (19)	C7—H7	0.9500
Sn1—N1ⁱ	2.3646 (19)	C8—C9	1.410 (3)
Sn2—C12ⁱⁱ	2.126 (2)	C8—C10	1.433 (4)
Sn2—C12	2.126 (2)	C9—C9ⁱ	1.440 (5)
Sn2—N4ⁱⁱ	2.302 (2)	C10—C10ⁱ	1.347 (6)
Sn2—N4	2.302 (2)	C10—H10	0.9500
Sn2—N3	2.3215 (18)	C12—C13	1.516 (3)
Sn2—N3ⁱⁱ	2.3215 (18)	C12—H12A	0.9900
S1—C11	1.616 (3)	C12—H12B	0.9900
S2—C22	1.641 (3)	C13—C14	1.521 (4)
N1—C5	1.326 (3)	C13—H13A	0.9900
N1—C9	1.357 (3)	C13—H13B	0.9900
N2—C11	1.159 (3)	C14—C15	1.502 (4)
N3—C16	1.335 (3)	C14—H14A	0.9900
N3—C20	1.360 (3)	C14—H14B	0.9900
N4—C22	1.102 (3)	C15—H15A	0.9800
C1—C2	1.526 (3)	C15—H15B	0.9800
C1—H1A	0.9900	C15—H15C	0.9800
C1—H1B	0.9900	C16—C17	1.399 (3)
C2—C3	1.527 (4)	C16—H16	0.9500
C2—H2A	0.9900	C17—C18	1.364 (3)
C2—H2B	0.9900	C17—H17	0.9500
C3—C4	1.525 (4)	C18—C19	1.413 (3)
C3—H3A	0.9900	C18—H18	0.9500
C3—H3B	0.9900	C19—C20	1.403 (3)
C4—H4A	0.9800	C19—C21	1.430 (3)
C4—H4B	0.9800	C20—C20ⁱⁱ	1.440 (4)
C4—H4C	0.9800	C21—C21ⁱⁱ	1.352 (5)
C5—C6	1.398 (3)	C21—H21	0.9500

C1ⁱ—Sn1—C1	177.93 (12)	N1—C5—C6	122.7 (2)
C1ⁱ—Sn1—N2ⁱ	90.57 (9)	N1—C5—H5	118.7
C1—Sn1—N2ⁱ	88.18 (8)	C6—C5—H5	118.7
C1ⁱ—Sn1—N2	88.18 (8)	C7—C6—C5	119.0 (3)
C1—Sn1—N2	90.57 (9)	C7—C6—H6	120.5
N2ⁱ—Sn1—N2	105.05 (11)	C5—C6—H6	120.5
C1ⁱ—Sn1—N1	87.78 (8)	C6—C7—C8	120.1 (2)
C1—Sn1—N1	93.91 (8)	C6—C7—H7	120.0
N2ⁱ—Sn1—N1	162.54 (7)	C8—C7—H7	120.0
N2—Sn1—N1	92.27 (7)	C7—C8—C9	117.4 (2)
C1ⁱ—Sn1—N1ⁱ	93.91 (8)	C7—C8—C10	123.5 (2)
C1—Sn1—N1ⁱ	87.78 (8)	C9—C8—C10	119.1 (2)
N2ⁱ—Sn1—N1ⁱ	92.27 (7)	N1—C9—C8	122.0 (2)
N2—Sn1—N1ⁱ	162.54 (7)	N1—C9—C9ⁱ	118.39 (13)
N1—Sn1—N1ⁱ	70.53 (9)	C8—C9—C9ⁱ	119.65 (15)
C12ⁱⁱ—Sn2—C12	170.80 (13)	C10ⁱ—C10—C8	121.30 (15)
C12ⁱⁱ—Sn2—N4ⁱⁱ	86.55 (8)	C10ⁱ—C10—H10	119.4
C12—Sn2—N4ⁱⁱ	88.12 (8)	C8—C10—H10	119.4
C12ⁱⁱ—Sn2—N4	88.12 (8)	N2—C11—S1	179.1 (2)
C12—Sn2—N4	86.55 (8)	C13—C12—Sn2	115.99 (15)
N4ⁱⁱ—Sn2—N4	109.11 (11)	C13—C12—H12A	108.3
C12ⁱⁱ—Sn2—N3	94.02 (8)	Sn2—C12—H12A	108.3
C12—Sn2—N3	93.44 (8)	C13—C12—H12B	108.3
N4ⁱⁱ—Sn2—N3	161.22 (7)	Sn2—C12—H12B	108.3
N4—Sn2—N3	89.68 (7)	H12A—C12—H12B	107.4
C12ⁱⁱ—Sn2—N3ⁱⁱ	93.44 (8)	C12—C13—C14	114.0 (2)
C12—Sn2—N3ⁱⁱ	94.02 (8)	C12—C13—H13A	108.8
N4ⁱⁱ—Sn2—N3ⁱⁱ	89.68 (7)	C14—C13—H13A	108.8
N4—Sn2—N3ⁱⁱ	161.22 (7)	C12—C13—H13B	108.8
N3—Sn2—N3ⁱⁱ	71.54 (9)	C14—C13—H13B	108.8
C5—N1—C9	118.9 (2)	H13A—C13—H13B	107.6
C5—N1—Sn1	124.72 (15)	C15—C14—C13	112.7 (2)
C9—N1—Sn1	116.34 (15)	C15—C14—H14A	109.1
C11—N2—Sn1	168.4 (2)	C13—C14—H14A	109.1
C16—N3—C20	118.75 (19)	C15—C14—H14B	109.1
C16—N3—Sn2	124.96 (15)	C13—C14—H14B	109.1
C20—N3—Sn2	116.29 (14)	H14A—C14—H14B	107.8
C22—N4—Sn2	173.9 (2)	C14—C15—H15A	109.5
C2—C1—Sn1	114.26 (17)	C14—C15—H15B	109.5
C2—C1—H1A	108.7	H15A—C15—H15B	109.5
Sn1—C1—H1A	108.7	C14—C15—H15C	109.5
C2—C1—H1B	108.7	H15A—C15—H15C	109.5
Sn1—C1—H1B	108.7	H15B—C15—H15C	109.5
H1A—C1—H1B	107.6	N3—C16—C17	122.2 (2)
C1—C2—C3	112.9 (2)	N3—C16—H16	118.9
C1—C2—H2A	109.0	C17—C16—H16	118.9
C3—C2—H2A	109.0	C18—C17—C16	119.5 (2)
C1—C2—H2B	109.0	C18—C17—H17	120.2
C3—C2—H2B	109.0	C16—C17—H17	120.2
H2A—C2—H2B	107.8	C17—C18—C19	119.8 (2)
C4—C3—C2	111.7 (3)	C17—C18—H18	120.1
C4—C3—H3A	109.3	C19—C18—H18	120.1
C2—C3—H3A	109.3	C20—C19—C18	117.3 (2)
C4—C3—H3B	109.3	C20—C19—C21	119.4 (2)
C2—C3—H3B	109.3	C18—C19—C21	123.3 (2)
H3A—C3—H3B	107.9	N3—C20—C19	122.4 (2)
C3—C4—H4A	109.5	N3—C20—C20ⁱⁱ	117.94 (12)
C3—C4—H4B	109.5	C19—C20—C20ⁱⁱ	119.61 (14)
H4A—C4—H4B	109.5	C21ⁱⁱ—C21—C19	121.02 (14)
C3—C4—H4C	109.5	C21ⁱⁱ—C21—H21	119.5
H4A—C4—H4C	109.5	C19—C21—H21	119.5
H4B—C4—H4C	109.5	N4—C22—S2	177.7 (2)

C1ⁱ—Sn1—N1—C5	−83.32 (19)	C6—C7—C8—C9	1.1 (4)
C1—Sn1—N1—C5	95.49 (18)	C6—C7—C8—C10	−178.7 (3)
N2ⁱ—Sn1—N1—C5	−168.1 (2)	C5—N1—C9—C8	−1.6 (3)
N2—Sn1—N1—C5	4.76 (18)	Sn1—N1—C9—C8	−179.73 (16)
N1ⁱ—Sn1—N1—C5	−178.3 (2)	C5—N1—C9—C9ⁱ	178.8 (2)
C1ⁱ—Sn1—N1—C9	94.70 (16)	Sn1—N1—C9—C9ⁱ	0.7 (3)
C1—Sn1—N1—C9	−86.49 (16)	C7—C8—C9—N1	0.5 (3)
N2ⁱ—Sn1—N1—C9	9.9 (3)	C10—C8—C9—N1	−179.6 (2)
N2—Sn1—N1—C9	−177.21 (15)	C7—C8—C9—C9ⁱ	−179.9 (3)
N1ⁱ—Sn1—N1—C9	−0.24 (11)	C10—C8—C9—C9ⁱ	0.0 (4)
C1ⁱ—Sn1—N2—C11	51.6 (10)	C7—C8—C10—C10ⁱ	−179.9 (3)
C1—Sn1—N2—C11	−130.1 (10)	C9—C8—C10—C10ⁱ	0.3 (5)
N2ⁱ—Sn1—N2—C11	141.7 (10)	N4ⁱⁱ—Sn2—C12—C13	−67.64 (18)
N1—Sn1—N2—C11	−36.1 (10)	N4—Sn2—C12—C13	−176.91 (18)
N1ⁱ—Sn1—N2—C11	−45.7 (11)	N3—Sn2—C12—C13	93.62 (17)
C12ⁱⁱ—Sn2—N3—C16	−88.13 (19)	N3ⁱⁱ—Sn2—C12—C13	21.90 (18)
C12—Sn2—N3—C16	86.48 (19)	Sn2—C12—C13—C14	173.58 (16)
N4ⁱⁱ—Sn2—N3—C16	−179.2 (2)	C12—C13—C14—C15	−177.8 (2)
N4—Sn2—N3—C16	−0.05 (18)	C20—N3—C16—C17	−0.7 (3)
N3ⁱⁱ—Sn2—N3—C16	179.6 (2)	Sn2—N3—C16—C17	179.63 (18)
C12ⁱⁱ—Sn2—N3—C20	92.20 (16)	N3—C16—C17—C18	0.2 (4)
C12—Sn2—N3—C20	−93.18 (16)	C16—C17—C18—C19	0.8 (4)
N4ⁱⁱ—Sn2—N3—C20	1.1 (3)	C17—C18—C19—C20	−1.2 (4)
N4—Sn2—N3—C20	−179.71 (16)	C17—C18—C19—C21	179.1 (2)
N3ⁱⁱ—Sn2—N3—C20	−0.09 (11)	C16—N3—C20—C19	0.3 (3)
N2ⁱ—Sn1—C1—C2	62.44 (19)	Sn2—N3—C20—C19	179.99 (17)
N2—Sn1—C1—C2	−42.61 (19)	C16—N3—C20—C20ⁱⁱ	−179.4 (2)
N1—Sn1—C1—C2	−134.92 (19)	Sn2—N3—C20—C20ⁱⁱ	0.3 (3)
N1ⁱ—Sn1—C1—C2	154.78 (19)	C18—C19—C20—N3	0.6 (3)
Sn1—C1—C2—C3	−166.65 (18)	C21—C19—C20—N3	−179.6 (2)
C1—C2—C3—C4	−176.4 (2)	C18—C19—C20—C20ⁱⁱ	−179.6 (3)
C9—N1—C5—C6	1.0 (3)	C21—C19—C20—C20ⁱⁱ	0.1 (4)
Sn1—N1—C5—C6	178.97 (18)	C20—C19—C21—C21ⁱⁱ	−0.7 (5)
N1—C5—C6—C7	0.6 (4)	C18—C19—C21—C21ⁱⁱ	179.1 (3)
C5—C6—C7—C8	−1.7 (4)

Symmetry codes: (i) −x+3/2, y, −z+1/2; (ii) −x+3/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(NCS)₂(C₁₂H₈N₂]
M_r	529.28
Crystal system, space group	Monoclinic, P2/n
Temperature (K)	100
a, b, c (Å)	15.0008 (3), 10.5220 (2), 15.8359 (3)
β (°)	107.452 (2)
V (Å³)	2384.46 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.30 × 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	0.703, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	11981, 5323, 4659
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 1.02
No. of reflections	5323
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.61

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, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Ganis, P., Peruzzo, V. & Valle, G. (1983). J. Organomet. Chem. 256, 245–250. 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