[6-(Furan-2-ylideneamino)-1,3-benzothia­zole-2-thiol­ato-κS²]triphenyl­tin(IV) ethanol hemisolvate

The title compound, [Sn(C₆H₅)₃(C₁₂H₇N₂OS₂)]·0.5C₂H₆O, shows a distorted tetra­hedral coordination of the Sn atom. The crystal packing is determined by van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.012 Å
• Disorder in solvent or counterion
• R factor = 0.052
• wR factor = 0.157
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C31
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

[6-(Furan-2-ylideneamino)-1,3-benzothiazole-2- thiolato-κS²]triphenyltin(IV) ethanol hemisolvate

Crystal data

[Sn(C6H5)3(C12H7N2OS2)]·0.5C2H6O	Z = 2
Mr = 632.34	F(000) = 638
Triclinic, P1	Dx = 1.392 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.685 (2) Å	Cell parameters from 1885 reflections
b = 13.204 (3) Å	θ = 2.5–20.5°
c = 13.323 (3) Å	µ = 1.01 mm^−1
α = 68.117 (4)°	T = 298 K
β = 76.261 (4)°	Block, yellow
γ = 75.145 (4)°	0.21 × 0.16 × 0.11 mm
V = 1508.8 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5267 independent reflections
Radiation source: fine-focus sealed tube	3313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.816, Tmax = 0.897	k = −15→15
8021 measured reflections	l = −15→8

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0829P)^2] where P = (Fo^2 + 2Fc^2)/3
5267 reflections	(Δ/σ)max < 0.001
353 parameters	Δρmax = 0.78 e Å^−3
39 restraints	Δρmin = −0.44 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.62923 (5)	0.81468 (4)	0.18265 (4)	0.0602 (2)
N1	0.5352 (6)	0.6989 (4)	0.4207 (4)	0.0567 (14)
N2	0.2618 (6)	0.5531 (5)	0.8550 (5)	0.0645 (15)
O1	0.1176 (6)	0.4928 (5)	1.0755 (5)	0.0963 (17)
O2	0.980 (2)	0.9471 (13)	0.5259 (16)	0.174 (6)	0.50
H2	1.0042	1.0076	0.4936	0.261*	0.50
S1	0.7013 (2)	0.52911 (16)	0.53436 (15)	0.0706 (5)
S2	0.78609 (19)	0.65514 (16)	0.29421 (15)	0.0705 (5)
C1	0.6616 (7)	0.6353 (6)	0.4139 (5)	0.0584 (17)
C2	0.4621 (7)	0.6656 (5)	0.5271 (5)	0.0561 (16)
C3	0.3238 (7)	0.7186 (6)	0.5620 (6)	0.0669 (19)
H3	0.2743	0.7804	0.5136	0.080*
C4	0.2639 (7)	0.6769 (6)	0.6694 (6)	0.0646 (19)
H4	0.1711	0.7101	0.6931	0.078*
C5	0.3372 (7)	0.5857 (5)	0.7454 (6)	0.0599 (17)
C6	0.4736 (7)	0.5334 (5)	0.7110 (6)	0.0597 (17)
H6	0.5236	0.4722	0.7596	0.072*
C7	0.5335 (7)	0.5751 (5)	0.6018 (5)	0.0531 (16)
C8	0.3296 (8)	0.5010 (6)	0.9343 (6)	0.0618 (18)
H8	0.4301	0.4839	0.9199	0.074*
C9	0.2595 (8)	0.4666 (6)	1.0462 (6)	0.0623 (18)
C10	0.3238 (7)	0.4160 (7)	1.1332 (6)	0.068 (2)
H10	0.4228	0.3927	1.1337	0.082*
C11	0.2167 (11)	0.4040 (7)	1.2232 (7)	0.088 (2)
H11	0.2309	0.3684	1.2957	0.106*
C12	0.0932 (10)	0.4503 (7)	1.1905 (7)	0.080 (2)
H12	0.0037	0.4548	1.2353	0.096*
C13	0.5696 (7)	0.9498 (6)	0.2444 (5)	0.0597 (17)
C14	0.4430 (9)	1.0199 (7)	0.2289 (7)	0.089 (2)
H14	0.3819	1.0086	0.1914	0.107*
C15	0.4014 (11)	1.1090 (8)	0.2676 (9)	0.119 (4)
H15	0.3129	1.1562	0.2558	0.143*
C16	0.4876 (11)	1.1282 (8)	0.3222 (8)	0.100 (3)
H16	0.4595	1.1878	0.3483	0.119*
C17	0.6130 (12)	1.0598 (9)	0.3376 (10)	0.124 (4)
H17	0.6738	1.0714	0.3752	0.148*
C18	0.6549 (10)	0.9710 (8)	0.2984 (9)	0.109 (3)
H18	0.7442	0.9249	0.3095	0.131*
C19	0.7861 (7)	0.8441 (5)	0.0372 (5)	0.0567 (16)
C20	0.8246 (8)	0.9491 (6)	−0.0184 (7)	0.081 (2)
H20	0.7777	1.0091	0.0051	0.097*
C21	0.9330 (10)	0.9619 (7)	−0.1085 (7)	0.098 (3)
H21	0.9601	1.0309	−0.1448	0.118*
C22	1.0010 (9)	0.8747 (8)	−0.1451 (7)	0.092 (3)
H22	1.0732	0.8850	−0.2062	0.110*
C23	0.9637 (9)	0.7730 (7)	−0.0928 (7)	0.086 (2)
H23	1.0097	0.7139	−0.1178	0.103*
C24	0.8554 (8)	0.7585 (6)	−0.0011 (6)	0.0686 (19)
H24	0.8299	0.6890	0.0347	0.082*
C25	0.4477 (7)	0.7717 (5)	0.1540 (6)	0.0568 (16)
C26	0.4473 (8)	0.7694 (6)	0.0519 (6)	0.072 (2)
H26	0.5272	0.7836	−0.0024	0.086*
C27	0.3282 (10)	0.7461 (7)	0.0292 (8)	0.089 (2)
H27	0.3282	0.7460	−0.0406	0.107*
C28	0.2100 (10)	0.7233 (7)	0.1097 (9)	0.090 (3)
H28	0.1311	0.7066	0.0945	0.108*
C29	0.2091 (8)	0.7251 (6)	0.2104 (8)	0.084 (2)
H29	0.1289	0.7103	0.2643	0.101*
C30	0.3270 (8)	0.7491 (6)	0.2349 (6)	0.071 (2)
H30	0.3253	0.7501	0.3046	0.086*
C31	0.983 (2)	0.8996 (16)	0.4563 (16)	0.125 (6)	0.50
H31A	1.0810	0.8949	0.4158	0.150*	0.50
H31B	0.9207	0.9506	0.4046	0.150*	0.50
C32	0.946 (3)	0.7898 (18)	0.488 (2)	0.169 (9)	0.50
H32A	0.8829	0.7748	0.5572	0.253*	0.50
H32B	1.0322	0.7341	0.4937	0.253*	0.50
H32C	0.8973	0.7886	0.4333	0.253*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0559 (3)	0.0667 (3)	0.0645 (4)	−0.0129 (2)	−0.0034 (2)	−0.0317 (3)
N1	0.060 (3)	0.061 (3)	0.048 (3)	−0.009 (3)	−0.010 (3)	−0.017 (3)
N2	0.059 (3)	0.069 (4)	0.059 (4)	−0.008 (3)	−0.001 (3)	−0.020 (3)
O1	0.082 (4)	0.108 (4)	0.098 (5)	−0.004 (3)	−0.011 (3)	−0.044 (4)
O2	0.159 (8)	0.183 (10)	0.156 (9)	−0.016 (8)	−0.052 (7)	−0.024 (7)
S1	0.0633 (11)	0.0714 (12)	0.0620 (12)	0.0065 (9)	−0.0038 (9)	−0.0215 (10)
S2	0.0600 (11)	0.0819 (13)	0.0612 (12)	−0.0061 (9)	0.0012 (9)	−0.0257 (10)
C1	0.056 (4)	0.068 (4)	0.056 (4)	−0.007 (3)	−0.012 (3)	−0.027 (4)
C2	0.062 (4)	0.057 (4)	0.055 (4)	−0.010 (3)	−0.010 (3)	−0.025 (3)
C3	0.061 (4)	0.065 (4)	0.060 (5)	0.000 (3)	−0.010 (4)	−0.012 (4)
C4	0.049 (4)	0.070 (5)	0.063 (5)	0.009 (3)	−0.011 (3)	−0.022 (4)
C5	0.066 (4)	0.057 (4)	0.057 (4)	−0.013 (3)	−0.001 (3)	−0.022 (4)
C6	0.060 (4)	0.056 (4)	0.057 (4)	0.001 (3)	−0.013 (3)	−0.018 (3)
C7	0.055 (4)	0.050 (4)	0.055 (4)	−0.002 (3)	−0.013 (3)	−0.021 (3)
C8	0.059 (4)	0.067 (5)	0.062 (5)	−0.017 (3)	−0.008 (4)	−0.022 (4)
C9	0.064 (5)	0.058 (4)	0.065 (5)	−0.019 (3)	0.003 (4)	−0.025 (4)
C10	0.044 (4)	0.114 (6)	0.051 (4)	−0.007 (4)	−0.012 (3)	−0.035 (4)
C11	0.105 (7)	0.089 (6)	0.063 (5)	−0.008 (5)	−0.023 (5)	−0.015 (5)
C12	0.082 (6)	0.092 (6)	0.070 (6)	−0.033 (5)	0.019 (5)	−0.040 (5)
C13	0.050 (4)	0.071 (4)	0.061 (4)	−0.012 (3)	0.001 (3)	−0.030 (4)
C14	0.087 (6)	0.092 (6)	0.113 (7)	−0.004 (5)	−0.036 (5)	−0.057 (5)
C15	0.106 (7)	0.101 (7)	0.175 (11)	0.031 (6)	−0.056 (7)	−0.087 (8)
C16	0.112 (8)	0.091 (7)	0.121 (8)	0.001 (6)	−0.032 (6)	−0.068 (6)
C17	0.127 (9)	0.118 (8)	0.174 (11)	0.006 (7)	−0.065 (8)	−0.096 (8)
C18	0.090 (6)	0.108 (7)	0.165 (9)	0.018 (5)	−0.061 (6)	−0.085 (7)
C19	0.049 (4)	0.061 (4)	0.064 (4)	−0.007 (3)	−0.009 (3)	−0.027 (4)
C20	0.079 (5)	0.070 (5)	0.085 (6)	−0.009 (4)	−0.002 (4)	−0.026 (5)
C21	0.119 (7)	0.076 (6)	0.081 (6)	−0.038 (5)	0.005 (5)	−0.005 (5)
C22	0.095 (6)	0.099 (7)	0.070 (6)	−0.022 (5)	0.015 (5)	−0.029 (5)
C23	0.096 (6)	0.081 (6)	0.082 (6)	−0.019 (5)	0.008 (5)	−0.040 (5)
C24	0.084 (5)	0.058 (4)	0.069 (5)	−0.024 (4)	0.001 (4)	−0.028 (4)
C25	0.051 (4)	0.051 (4)	0.070 (5)	−0.003 (3)	−0.009 (3)	−0.026 (4)
C26	0.073 (5)	0.070 (5)	0.083 (6)	−0.010 (4)	−0.014 (4)	−0.039 (4)
C27	0.098 (7)	0.087 (6)	0.101 (7)	−0.010 (5)	−0.044 (6)	−0.040 (5)
C28	0.085 (6)	0.079 (6)	0.124 (8)	−0.018 (5)	−0.042 (6)	−0.036 (6)
C29	0.061 (5)	0.075 (5)	0.113 (7)	−0.012 (4)	−0.022 (5)	−0.023 (5)
C30	0.068 (5)	0.070 (5)	0.076 (5)	−0.010 (4)	−0.018 (4)	−0.022 (4)
C31	0.103 (8)	0.127 (9)	0.127 (9)	0.007 (7)	−0.043 (8)	−0.026 (7)
C32	0.141 (11)	0.189 (12)	0.161 (11)	−0.029 (9)	−0.043 (8)	−0.031 (8)

Geometric parameters (Å, º)

Sn1—C13	2.129 (7)	C14—H14	0.9300
Sn1—C25	2.133 (7)	C15—C16	1.351 (12)
Sn1—C19	2.135 (6)	C15—H15	0.9300
Sn1—S2	2.460 (2)	C16—C17	1.322 (12)
N1—C1	1.300 (8)	C16—H16	0.9300
N1—C2	1.386 (8)	C17—C18	1.387 (12)
N2—C8	1.257 (8)	C17—H17	0.9300
N2—C5	1.427 (8)	C18—H18	0.9300
O1—C9	1.328 (8)	C19—C24	1.366 (9)
O1—C12	1.405 (9)	C19—C20	1.406 (9)
O2—C31	1.289 (16)	C20—C21	1.383 (11)
O2—O2^i	1.42 (3)	C20—H20	0.9300
O2—H2	0.8200	C21—C22	1.370 (11)
S1—C7	1.739 (6)	C21—H21	0.9300
S1—C1	1.740 (7)	C22—C23	1.360 (10)
S2—C1	1.733 (7)	C22—H22	0.9300
C2—C7	1.384 (9)	C23—C24	1.396 (10)
C2—C3	1.403 (9)	C23—H23	0.9300
C3—C4	1.367 (9)	C24—H24	0.9300
C3—H3	0.9300	C25—C26	1.372 (9)
C4—C5	1.405 (9)	C25—C30	1.400 (9)
C4—H4	0.9300	C26—C27	1.391 (10)
C5—C6	1.382 (9)	C26—H26	0.9300
C6—C7	1.386 (9)	C27—C28	1.380 (11)
C6—H6	0.9300	C27—H27	0.9300
C8—C9	1.436 (9)	C28—C29	1.350 (12)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.315 (9)	C29—C30	1.397 (10)
C10—C11	1.375 (10)	C29—H29	0.9300
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.292 (11)	C31—C32	1.469 (16)
C11—H11	0.9300	C31—H31A	0.9700
C12—H12	0.9300	C31—H31B	0.9700
C13—C14	1.341 (10)	C32—H32A	0.9600
C13—C18	1.353 (10)	C32—H32B	0.9600
C14—C15	1.386 (11)	C32—H32C	0.9600
C13—Sn1—C25	112.7 (2)	C17—C16—C15	118.2 (9)
C13—Sn1—C19	112.6 (2)	C17—C16—H16	120.9
C25—Sn1—C19	109.5 (3)	C15—C16—H16	120.9
C13—Sn1—S2	112.1 (2)	C16—C17—C18	120.8 (9)
C25—Sn1—S2	113.45 (17)	C16—C17—H17	119.6
C19—Sn1—S2	95.30 (18)	C18—C17—H17	119.6
C1—N1—C2	109.9 (5)	C13—C18—C17	121.8 (8)
C8—N2—C5	120.7 (6)	C13—C18—H18	119.1
C9—O1—C12	105.5 (6)	C17—C18—H18	119.1
C31—O2—O2^i	112 (2)	C24—C19—C20	118.7 (6)
C31—O2—H2	109.6	C24—C19—Sn1	119.7 (5)
C7—S1—C1	89.4 (3)	C20—C19—Sn1	121.5 (5)
C1—S2—Sn1	95.3 (2)	C21—C20—C19	119.1 (7)
N1—C1—S2	122.9 (5)	C21—C20—H20	120.4
N1—C1—S1	115.8 (5)	C19—C20—H20	120.4
S2—C1—S1	121.3 (4)	C22—C21—C20	121.0 (8)
C7—C2—N1	116.5 (6)	C22—C21—H21	119.5
C7—C2—C3	119.4 (6)	C20—C21—H21	119.5
N1—C2—C3	124.1 (6)	C23—C22—C21	120.4 (8)
C4—C3—C2	118.0 (6)	C23—C22—H22	119.8
C4—C3—H3	121.0	C21—C22—H22	119.8
C2—C3—H3	121.0	C22—C23—C24	119.3 (7)
C3—C4—C5	122.4 (6)	C22—C23—H23	120.4
C3—C4—H4	118.8	C24—C23—H23	120.4
C5—C4—H4	118.8	C19—C24—C23	121.5 (7)
C6—C5—C4	119.5 (6)	C19—C24—H24	119.3
C6—C5—N2	124.5 (6)	C23—C24—H24	119.3
C4—C5—N2	115.9 (6)	C26—C25—C30	118.9 (7)
C5—C6—C7	117.9 (6)	C26—C25—Sn1	119.0 (5)
C5—C6—H6	121.0	C30—C25—Sn1	122.1 (5)
C7—C6—H6	121.0	C25—C26—C27	120.5 (8)
C2—C7—C6	122.7 (6)	C25—C26—H26	119.8
C2—C7—S1	108.4 (5)	C27—C26—H26	119.8
C6—C7—S1	128.9 (5)	C28—C27—C26	120.3 (8)
N2—C8—C9	123.1 (7)	C28—C27—H27	119.9
N2—C8—H8	118.4	C26—C27—H27	119.9
C9—C8—H8	118.4	C29—C28—C27	119.9 (8)
C10—C9—O1	110.5 (6)	C29—C28—H28	120.1
C10—C9—C8	126.3 (7)	C27—C28—H28	120.1
O1—C9—C8	122.9 (7)	C28—C29—C30	120.9 (8)
C9—C10—C11	107.0 (7)	C28—C29—H29	119.6
C9—C10—H10	126.5	C30—C29—H29	119.6
C11—C10—H10	126.5	C29—C30—C25	119.6 (8)
C12—C11—C10	108.8 (7)	C29—C30—H30	120.2
C12—C11—H11	125.6	C25—C30—H30	120.2
C10—C11—H11	125.6	O2—C31—C32	123.3 (18)
C11—C12—O1	108.1 (7)	O2—C31—H31A	106.5
C11—C12—H12	126.0	C32—C31—H31A	106.5
O1—C12—H12	126.0	O2—C31—H31B	106.5
C14—C13—C18	116.7 (7)	C32—C31—H31B	106.5
C14—C13—Sn1	120.0 (6)	H31A—C31—H31B	106.5
C18—C13—Sn1	123.2 (6)	C31—C32—H32A	109.5
C13—C14—C15	121.4 (8)	C31—C32—H32B	109.5
C13—C14—H14	119.3	H32A—C32—H32B	109.5
C15—C14—H14	119.3	C31—C32—H32C	109.5
C16—C15—C14	120.9 (8)	H32A—C32—H32C	109.5
C16—C15—H15	119.5	H32B—C32—H32C	109.5
C14—C15—H15	119.5

Symmetry code: (i) −x+2, −y+2, −z+1.