Synthesis, detailed geometric analysis and bond-valence method evaluation of the strength of π-arene bonding of two isotypic cationic prehnitene tin(II) complexes: [{1,2,3,4-(CH₃)₄C₆H₂}₂Sn₂Cl₂][MCl₄]₂ (M = Al and Ga)

The first main-group-metal–prehnitene π complexes have been obtained in form of the isotypic pair {[{1,2,3,4-(CH₃)₄C₆H₂}₂Sn₂Cl₂][MCl₄]₂}_x (M = Al, Ga) and crystal structure determinations thereof give strong evidence that a distorted η⁶ coordination mode, characterized by a small but significant ring slippage of ca 0.4 Å as well as a pronounced tilt of the plane of the arene ligand against the plane of the central (Sn₂Cl₂)²⁺ four-membered ring species, is an intrinsic feature of this kind of arene complexed dimeric chlorido­stannylene cation. Application of the bond-valence method in a indirect manner yields empirical bond valences of 0.38 and 0.37, respectively, which allow for classifying the metal–π-arene bonding as a strong non-covalent inter­action, which is in line with the expectation that [AlCl₄]⁻ is the slightly weaker coordinating anion as compared to [GaCl₄]⁻.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.058
• Data-to-parameter ratio = 29.0

Structure: II

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.069
• Data-to-parameter ratio = 29.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Al1 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.289 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.005 Degree
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.59 Ratio
PLAT794_ALERT_5_G Tentative Bond Valency for Sn1       (II)      .       1.50 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Al1       (III)     .       3.05 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

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




Datablock: II


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Ga1 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.148 Check

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.61 mm
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.59 Ratio
PLAT794_ALERT_5_G Tentative Bond Valency for Sn1       (II)      .       1.51 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Ga1       (III)     .       3.04 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

For both structures, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2018); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[chloridoaluminate(III)]-tri-µ-chlorido-4':1κ²Cl,1:2κ⁴Cl-[(η⁶-1,2,3,4-tetramethylbenzene)tin(II)]-di-µ-chlorido-2:3κ⁴Cl-[(η⁶-1,2,3,4-tetramethylbenzene)tin(II)]-di-µ-chlorido-3:4κ⁴Cl-[chloridoaluminate(III)]-µ-chlorido-4:1'κ²Cl] (I)

Crystal data

[Al2Sn2Cl10(C10H14)2]	Z = 1
Mr = 914.30	F(000) = 444
Triclinic, P1	Dx = 1.769 Mg m^−3
a = 8.7512 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1357 (6) Å	Cell parameters from 24404 reflections
c = 11.2803 (7) Å	θ = 4.5–59.3°
α = 85.524 (5)°	µ = 2.30 mm^−1
β = 72.769 (5)°	T = 213 K
γ = 86.926 (5)°	Needle, colorless
V = 858.30 (9) Å^3	0.27 × 0.17 × 0.13 mm

Data collection

Stoe IPDS 2T diffractometer	4326 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
ω scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −11→11
Tmin = 0.476, Tmax = 0.697	k = −12→12
17750 measured reflections	l = −15→15
4585 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0163P)^2 + 0.5546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.24	(Δ/σ)max = 0.001
4585 reflections	Δρmax = 0.59 e Å^−3
158 parameters	Δρmin = −0.46 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
Sn1	0.52308 (2)	0.16549 (2)	0.60211 (2)	0.02833 (5)
Cl1	0.29871 (6)	0.01611 (6)	0.55845 (5)	0.03375 (12)
Cl2	0.52884 (7)	0.36374 (7)	0.37225 (6)	0.03974 (13)
Cl3	0.85918 (10)	0.32842 (9)	0.47942 (8)	0.05591 (19)
Cl4	0.80050 (8)	0.64593 (6)	0.30806 (7)	0.04703 (16)
Cl5	0.90510 (11)	0.32035 (10)	0.15790 (8)	0.0646 (2)
Al1	0.78043 (9)	0.41345 (7)	0.32595 (7)	0.03229 (15)
C1	0.6234 (3)	−0.0503 (3)	0.7664 (2)	0.0366 (5)
H1	0.671568	−0.133161	0.723925	0.044*
C2	0.4588 (3)	−0.0430 (3)	0.8189 (2)	0.0335 (5)
H2	0.397040	−0.120733	0.811111	0.040*
C3	0.3833 (3)	0.0780 (3)	0.8831 (2)	0.0305 (4)
C4	0.4771 (3)	0.1937 (3)	0.8931 (2)	0.0330 (5)
C5	0.6446 (3)	0.1861 (3)	0.8393 (2)	0.0349 (5)
C6	0.7188 (3)	0.0631 (3)	0.7757 (2)	0.0358 (5)
C7	0.2040 (3)	0.0788 (3)	0.9401 (3)	0.0434 (6)
H71	0.155733	0.161604	0.903607	0.065*
H72	0.178309	0.087089	1.029158	0.065*
H73	0.162684	−0.011828	0.924343	0.065*
C8	0.3978 (4)	0.3254 (3)	0.9619 (3)	0.0501 (7)
H81	0.418526	0.412853	0.905839	0.075*
H82	0.440483	0.336065	1.030844	0.075*
H83	0.283293	0.311956	0.993471	0.075*
C9	0.7448 (4)	0.3112 (4)	0.8510 (3)	0.0588 (8)
H91	0.855725	0.292126	0.804884	0.088*
H92	0.736307	0.319407	0.937973	0.088*
H93	0.706411	0.402187	0.817729	0.088*
C10	0.8978 (3)	0.0490 (4)	0.7171 (3)	0.0501 (7)
H101	0.923939	−0.041956	0.675420	0.075*
H102	0.951224	0.048501	0.781249	0.075*
H103	0.933184	0.131365	0.657192	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02904 (8)	0.02763 (8)	0.02706 (7)	−0.00218 (5)	−0.00572 (5)	−0.00324 (5)
Cl1	0.0225 (2)	0.0373 (3)	0.0385 (3)	−0.00117 (19)	−0.0019 (2)	−0.0127 (2)
Cl2	0.0330 (3)	0.0419 (3)	0.0428 (3)	−0.0057 (2)	−0.0084 (2)	−0.0019 (2)
Cl3	0.0568 (4)	0.0534 (4)	0.0656 (5)	−0.0169 (3)	−0.0332 (4)	0.0179 (3)
Cl4	0.0361 (3)	0.0256 (3)	0.0687 (4)	−0.0010 (2)	−0.0004 (3)	0.0026 (3)
Cl5	0.0581 (5)	0.0649 (5)	0.0572 (5)	0.0054 (4)	0.0080 (4)	−0.0241 (4)
Al1	0.0307 (3)	0.0257 (3)	0.0363 (4)	−0.0004 (3)	−0.0037 (3)	−0.0012 (3)
C1	0.0403 (13)	0.0347 (12)	0.0313 (11)	0.0071 (10)	−0.0066 (10)	−0.0016 (9)
C2	0.0368 (12)	0.0333 (11)	0.0307 (11)	−0.0060 (9)	−0.0102 (9)	0.0015 (9)
C3	0.0265 (10)	0.0389 (12)	0.0241 (10)	−0.0032 (9)	−0.0045 (8)	0.0007 (8)
C4	0.0337 (12)	0.0373 (12)	0.0279 (10)	−0.0004 (9)	−0.0079 (9)	−0.0066 (9)
C5	0.0300 (11)	0.0446 (13)	0.0318 (11)	−0.0072 (9)	−0.0103 (9)	−0.0030 (9)
C6	0.0261 (11)	0.0484 (14)	0.0308 (11)	0.0017 (9)	−0.0071 (9)	0.0034 (9)
C7	0.0281 (12)	0.0562 (16)	0.0408 (13)	−0.0037 (11)	−0.0039 (10)	0.0051 (11)
C8	0.0533 (17)	0.0464 (15)	0.0481 (16)	0.0030 (12)	−0.0075 (13)	−0.0196 (12)
C9	0.0485 (17)	0.067 (2)	0.065 (2)	−0.0225 (15)	−0.0179 (15)	−0.0148 (16)
C10	0.0274 (12)	0.0668 (19)	0.0498 (16)	0.0056 (12)	−0.0063 (11)	0.0099 (13)

Geometric parameters (Å, º)

Sn1—Cl1	2.6316 (6)	C2—H2	0.9400
Sn1—Cl1^i	2.6425 (6)	C3—C4	1.405 (3)
Sn1—Cl2	3.0340 (7)	C3—C7	1.509 (3)
Sn1—Cl3	3.2432 (8)	C4—C5	1.411 (3)
Sn1—Cl4^ii	3.1722 (7)	C4—C8	1.506 (3)
Sn1—C1	2.881 (2)	C5—C6	1.404 (4)
Sn1—C2	2.915 (2)	C5—C9	1.513 (4)
Sn1—C3	3.097 (2)	C6—C10	1.512 (3)
Sn1—C4	3.216 (2)	C7—H71	0.9700
Sn1—C5	3.181 (2)	C7—H72	0.9700
Sn1—C6	3.028 (2)	C7—H73	0.9700
Sn1—Al1	3.8983 (8)	C8—H81	0.9700
Sn1—Sn1^i	4.0476 (4)	C8—H82	0.9700
Al1—Cl2	2.1715 (9)	C8—H83	0.9700
Al1—Cl3	2.1249 (11)	C9—H91	0.9700
Al1—Cl4	2.1294 (9)	C9—H92	0.9700
Al1—Cl5	2.1058 (10)	C9—H93	0.9700
C1—C2	1.386 (4)	C10—H101	0.9700
C1—C6	1.393 (4)	C10—H102	0.9700
C1—H1	0.9400	C10—H103	0.9700
C2—C3	1.394 (3)
Cl1—Sn1—Cl1^i	79.753 (18)	Al1—Cl4—Sn1^ii	116.50 (3)
Cl1—Sn1—Cl2	88.426 (19)	Cl5—Al1—Cl3	113.35 (5)
Cl1—Sn1—Cl3	145.46 (2)	Cl5—Al1—Cl4	110.64 (5)
Cl1—Sn1—Cl4^ii	73.398 (18)	Cl3—Al1—Cl4	108.81 (5)
Cl1^i—Sn1—Cl2	84.476 (19)	Cl5—Al1—Cl2	109.07 (5)
Cl1^i—Sn1—Cl3	74.86 (2)	Cl3—Al1—Cl2	106.38 (4)
Cl1^i—Sn1—Cl4^ii	147.90 (2)	Cl4—Al1—Cl2	108.40 (4)
Cl2—Sn1—Cl3	66.360 (18)	C2—C1—C6	121.1 (2)
Cl2—Sn1—Cl4^ii	77.616 (19)	C2—C1—H1	119.4
Cl3—Sn1—Cl4^ii	120.01 (2)	C6—C1—H1	119.4
Cl1—Sn1—C1	98.59 (6)	C1—C2—C3	121.0 (2)
Cl1—Sn1—C2	80.90 (5)	C1—C2—H2	119.5
Cl1—Sn1—C3	89.06 (4)	C3—C2—H2	119.5
Cl1—Sn1—C4	113.59 (5)	C2—C3—C4	118.8 (2)
Cl1—Sn1—C5	133.54 (5)	C2—C3—C7	118.7 (2)
Cl1—Sn1—C6	125.60 (5)	C4—C3—C7	122.5 (2)
Cl1^i—Sn1—C1	78.92 (5)	C3—C4—C5	120.1 (2)
Cl1^i—Sn1—C2	96.51 (5)	C3—C4—C8	119.6 (2)
Cl1^i—Sn1—C3	122.99 (5)	C5—C4—C8	120.4 (2)
Cl1^i—Sn1—C4	131.87 (5)	C6—C5—C4	120.4 (2)
Cl1^i—Sn1—C5	113.02 (5)	C6—C5—C9	119.9 (2)
Cl1^i—Sn1—C6	87.77 (5)	C4—C5—C9	119.7 (2)
Cl2—Sn1—C1	160.46 (5)	C1—C6—C5	118.6 (2)
Cl2—Sn1—C2	168.90 (5)	C1—C6—C10	118.9 (3)
Cl2—Sn1—C3	151.42 (5)	C5—C6—C10	122.5 (3)
Cl2—Sn1—C4	138.73 (5)	C3—C7—H71	109.5
Cl2—Sn1—C5	135.45 (5)	C3—C7—H72	109.5
Cl2—Sn1—C6	143.03 (5)	H71—C7—H72	109.5
Cl3—Sn1—C1	99.07 (6)	C3—C7—H73	109.5
Cl3—Sn1—C2	124.60 (5)	H71—C7—H73	109.5
Cl3—Sn1—C3	124.44 (4)	H72—C7—H73	109.5
Cl3—Sn1—C4	100.80 (5)	C4—C8—H81	109.5
Cl3—Sn1—C5	78.78 (5)	C4—C8—H82	109.5
Cl3—Sn1—C6	76.71 (5)	H81—C8—H82	109.5
Cl4^ii—Sn1—C1	121.84 (5)	C4—C8—H83	109.5
Cl4^ii—Sn1—C2	96.29 (5)	H81—C8—H83	109.5
Cl4^ii—Sn1—C3	74.39 (5)	H82—C8—H83	109.5
Cl4^ii—Sn1—C4	76.28 (5)	C5—C9—H91	109.5
Cl4^ii—Sn1—C5	98.30 (5)	C5—C9—H92	109.5
Cl4^ii—Sn1—C6	122.18 (5)	H91—C9—H92	109.5
Sn1—Cl1—Sn1^i	100.247 (18)	C5—C9—H93	109.5
Sn1—C1—H1	110.9	H91—C9—H93	109.5
Sn1—C2—H2	111.8	H92—C9—H93	109.5
Sn1—C3—C7	119.14 (16)	C6—C10—H101	109.5
Sn1—C4—C8	123.29 (18)	C6—C10—H102	109.5
Sn1—C5—C9	122.01 (19)	H101—C10—H102	109.5
Sn1—C6—C10	116.23 (17)	C6—C10—H103	109.5
Al1—Cl2—Sn1	95.56 (3)	H101—C10—H103	109.5
Al1—Cl3—Sn1	90.68 (3)	H102—C10—H103	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H103···Cl3	0.97	2.79	3.633 (3)	146
C7—H71···Cl4^ii	0.97	2.80	3.622 (3)	144

Symmetry code: (ii) −x+1, −y+1, −z+1.

catena-Poly[[chloridogallate(III)]-tri-µ-chlorido-4':1κ²Cl,1:2κ⁴Cl-[(η⁶-1,2,3,4-tetramethylbenzene)tin(II)]-di-µ-chlorido-2:3κ⁴Cl-[(η⁶-1,2,3,4-tetramethylbenzene)tin(II)]-di-µ-chlorido-3:4κ⁴Cl-[chloridogallate(III)]-µ-chlorido-4:1'κ²Cl] (II)

Crystal data

[Ga2Sn2Cl10(C10H14)2]	Z = 1
Mr = 999.78	F(000) = 480
Triclinic, P1	Dx = 1.931 Mg m^−3
a = 8.7572 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1310 (4) Å	Cell parameters from 21911 reflections
c = 11.2966 (5) Å	θ = 4.5–59.3°
α = 85.424 (3)°	µ = 3.77 mm^−1
β = 72.805 (3)°	T = 213 K
γ = 86.886 (4)°	Needle, colourless
V = 859.73 (7) Å^3	0.61 × 0.13 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer	4242 reflections with I > 2σ(I)
ω scans	Rint = 0.048
Absorption correction: multi-scan (Blessing, 1995)	θmax = 29.2°, θmin = 2.2°
Tmin = 0.376, Tmax = 0.656	h = −11→11
17522 measured reflections	k = −12→11
4638 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0176P)^2 + 0.9105P] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max = 0.001
4638 reflections	Δρmax = 0.71 e Å^−3
158 parameters	Δρmin = −0.50 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
Sn1	0.52200 (3)	0.16597 (2)	0.60194 (2)	0.02838 (6)
Ga1	0.78103 (4)	0.41311 (3)	0.32615 (3)	0.03202 (8)
Cl1	0.29875 (9)	0.01494 (8)	0.55911 (7)	0.03389 (15)
Cl2	0.52418 (10)	0.36331 (9)	0.37434 (8)	0.03987 (17)
Cl3	0.86231 (14)	0.32600 (11)	0.48157 (11)	0.0565 (3)
Cl4	0.80145 (11)	0.65004 (8)	0.30948 (10)	0.0477 (2)
Cl5	0.90567 (15)	0.31991 (13)	0.15424 (11)	0.0646 (3)
C1	0.6226 (4)	−0.0506 (4)	0.7670 (3)	0.0372 (7)
H1	0.670505	−0.133397	0.724495	0.045*
C2	0.4589 (4)	−0.0435 (3)	0.8188 (3)	0.0332 (6)
H2	0.397444	−0.121308	0.810744	0.040*
C3	0.3829 (4)	0.0773 (3)	0.8831 (3)	0.0301 (6)
C4	0.4772 (4)	0.1935 (4)	0.8922 (3)	0.0331 (6)
C5	0.6443 (4)	0.1853 (4)	0.8391 (3)	0.0345 (6)
C6	0.7182 (4)	0.0618 (4)	0.7763 (3)	0.0358 (7)
C7	0.2046 (4)	0.0785 (4)	0.9400 (3)	0.0431 (8)
H71	0.156274	0.160251	0.902162	0.065*
H72	0.179189	0.089092	1.028578	0.065*
H73	0.163275	−0.012949	0.926109	0.065*
C8	0.3983 (5)	0.3255 (4)	0.9602 (4)	0.0503 (9)
H81	0.426066	0.413765	0.905725	0.075*
H82	0.434745	0.332000	1.032732	0.075*
H83	0.283145	0.315915	0.986078	0.075*
C9	0.7449 (5)	0.3105 (5)	0.8505 (4)	0.0570 (11)
H91	0.857192	0.285182	0.814368	0.085*
H92	0.725155	0.327596	0.937538	0.085*
H93	0.716585	0.398926	0.807067	0.085*
C10	0.8972 (4)	0.0473 (5)	0.7176 (4)	0.0492 (9)
H101	0.923751	−0.046929	0.681388	0.074*
H102	0.951087	0.053946	0.780598	0.074*
H103	0.931353	0.125718	0.653377	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03005 (11)	0.02753 (10)	0.02689 (10)	−0.00228 (7)	−0.00647 (8)	−0.00417 (7)
Ga1	0.03199 (18)	0.02486 (15)	0.03540 (18)	−0.00005 (13)	−0.00417 (14)	−0.00194 (13)
Cl1	0.0231 (3)	0.0373 (4)	0.0388 (4)	−0.0013 (3)	−0.0023 (3)	−0.0140 (3)
Cl2	0.0340 (4)	0.0420 (4)	0.0427 (4)	−0.0057 (3)	−0.0091 (3)	−0.0031 (3)
Cl3	0.0597 (6)	0.0533 (5)	0.0652 (6)	−0.0163 (5)	−0.0344 (5)	0.0165 (5)
Cl4	0.0363 (4)	0.0250 (3)	0.0707 (6)	−0.0008 (3)	−0.0001 (4)	0.0021 (3)
Cl5	0.0596 (6)	0.0660 (6)	0.0553 (6)	0.0052 (5)	0.0073 (5)	−0.0248 (5)
C1	0.0423 (18)	0.0354 (16)	0.0311 (15)	0.0067 (14)	−0.0080 (14)	−0.0029 (12)
C2	0.0396 (17)	0.0321 (14)	0.0291 (14)	−0.0074 (12)	−0.0116 (13)	0.0016 (11)
C3	0.0278 (14)	0.0381 (15)	0.0240 (13)	−0.0017 (12)	−0.0076 (11)	0.0011 (11)
C4	0.0346 (16)	0.0394 (15)	0.0254 (13)	0.0001 (12)	−0.0081 (12)	−0.0072 (11)
C5	0.0317 (15)	0.0440 (17)	0.0309 (14)	−0.0068 (13)	−0.0128 (13)	−0.0033 (12)
C6	0.0279 (15)	0.0471 (17)	0.0307 (14)	0.0038 (13)	−0.0076 (12)	0.0016 (13)
C7	0.0293 (16)	0.058 (2)	0.0371 (17)	−0.0052 (15)	−0.0031 (14)	0.0044 (15)
C8	0.052 (2)	0.048 (2)	0.050 (2)	0.0029 (17)	−0.0109 (18)	−0.0217 (17)
C9	0.047 (2)	0.065 (3)	0.064 (3)	−0.0206 (19)	−0.018 (2)	−0.013 (2)
C10	0.0277 (17)	0.066 (2)	0.049 (2)	0.0050 (16)	−0.0084 (15)	0.0106 (18)

Geometric parameters (Å, º)

Sn1—Cl1	2.6299 (8)	C2—H2	0.9400
Sn1—Cl1^i	2.6481 (7)	C3—C4	1.408 (4)
Sn1—Cl2	3.0155 (9)	C3—C7	1.503 (4)
Sn1—Cl3	3.2597 (11)	C4—C5	1.408 (5)
Sn1—Cl4^ii	3.1499 (9)	C4—C8	1.505 (5)
Sn1—C1	2.891 (3)	C5—C6	1.404 (5)
Sn1—C2	2.921 (3)	C5—C9	1.517 (5)
Sn1—C3	3.104 (3)	C6—C10	1.513 (5)
Sn1—C4	3.214 (3)	C7—H71	0.9700
Sn1—C5	3.185 (3)	C7—H72	0.9700
Sn1—C6	3.043 (3)	C7—H73	0.9700
Sn1—Ga1	3.8987 (4)	C8—H81	0.9700
Sn1—Sn1^i	4.0503 (4)	C8—H82	0.9700
Ga1—Cl2	2.2159 (9)	C8—H83	0.9700
Ga1—Cl3	2.1625 (10)	C9—H91	0.9700
Ga1—Cl4	2.1691 (8)	C9—H92	0.9700
Ga1—Cl5	2.1439 (10)	C9—H93	0.9700
C1—C2	1.379 (5)	C10—H101	0.9700
C1—C6	1.388 (5)	C10—H102	0.9700
C1—H1	0.9400	C10—H103	0.9700
C2—C3	1.395 (4)
Cl1—Sn1—Cl1^i	79.76 (2)	Cl5—Ga1—Cl2	109.01 (4)
Cl1—Sn1—Cl2	88.37 (3)	Cl3—Ga1—Cl2	106.43 (4)
Cl1^i—Sn1—Cl2	84.56 (3)	Cl4—Ga1—Cl2	108.21 (4)
Cl1—Sn1—Cl4^ii	73.00 (2)	Sn1—Cl1—Sn1^i	100.24 (2)
Cl1^i—Sn1—Cl4^ii	147.47 (3)	Ga1—Cl2—Sn1	95.14 (3)
Cl1—Sn1—Cl3	146.02 (3)	Ga1—Cl3—Sn1	89.58 (3)
Cl1^i—Sn1—Cl3	74.35 (3)	Ga1—Cl4—Sn1^ii	115.87 (3)
Cl2—Sn1—Cl3	67.82 (2)	C2—C1—C6	121.5 (3)
Cl2—Sn1—Cl4^ii	77.33 (2)	C2—C1—H1	119.2
Cl4^ii—Sn1—Cl3	121.37 (3)	C6—C1—H1	119.2
Cl1—Sn1—C1	98.21 (7)	C1—C2—C3	121.1 (3)
Cl1^i—Sn1—C1	79.15 (7)	C1—C2—H2	119.5
Cl1—Sn1—C2	80.68 (7)	C3—C2—H2	119.5
Cl1^i—Sn1—C2	96.61 (7)	C2—C3—C4	118.4 (3)
Cl1—Sn1—C3	88.88 (6)	C2—C3—C7	119.1 (3)
Cl1^i—Sn1—C3	123.05 (6)	C4—C3—C7	122.5 (3)
Cl1—Sn1—C4	113.52 (6)	C3—C4—C5	120.1 (3)
Cl1^i—Sn1—C4	131.84 (6)	C3—C4—C8	119.5 (3)
Cl1—Sn1—C5	133.20 (6)	C5—C4—C8	120.4 (3)
Cl1^i—Sn1—C5	112.86 (6)	C6—C5—C4	120.4 (3)
Cl1—Sn1—C6	125.01 (7)	C6—C5—C9	119.9 (3)
Cl1^i—Sn1—C6	87.73 (7)	C4—C5—C9	119.7 (3)
Cl2—Sn1—C1	161.00 (7)	C1—C6—C5	118.4 (3)
Cl2—Sn1—C2	168.57 (7)	C1—C6—C10	119.0 (3)
Cl2—Sn1—C3	151.20 (6)	C5—C6—C10	122.6 (3)
Cl2—Sn1—C4	138.75 (6)	C3—C7—H71	109.5
Cl2—Sn1—C5	135.87 (6)	C3—C7—H72	109.5
Cl2—Sn1—C6	143.69 (7)	H71—C7—H72	109.5
C1—Sn1—Cl3	98.11 (7)	C3—C7—H73	109.5
C2—Sn1—Cl3	123.48 (7)	H71—C7—H73	109.5
C3—Sn1—Cl3	123.69 (6)	H72—C7—H73	109.5
C4—Sn1—Cl3	100.17 (6)	C4—C8—H81	109.5
C5—Sn1—Cl3	78.09 (6)	C4—C8—H82	109.5
C6—Sn1—Cl3	75.93 (7)	H81—C8—H82	109.5
C1—Sn1—Cl4^ii	121.62 (7)	C4—C8—H83	109.5
C2—Sn1—Cl4^ii	96.19 (7)	H81—C8—H83	109.5
C3—Sn1—Cl4^ii	74.45 (6)	H82—C8—H83	109.5
Cl4^ii—Sn1—C4	76.64 (6)	C5—C9—H91	109.5
Cl4^ii—Sn1—C5	98.82 (7)	C5—C9—H92	109.5
C6—Sn1—Cl4^ii	122.46 (6)	H91—C9—H92	109.5
Sn1—C1—H1	110.6	C5—C9—H93	109.5
Sn1—C2—H2	111.6	H91—C9—H93	109.5
Sn1—C3—C7	119.1 (2)	H92—C9—H93	109.5
Sn1—C4—C8	123.0 (2)	C6—C10—H101	109.5
Sn1—C5—C9	121.9 (2)	C6—C10—H102	109.5
Sn1—C6—C10	116.1 (2)	H101—C10—H102	109.5
Cl5—Ga1—Cl3	113.84 (5)	C6—C10—H103	109.5
Cl5—Ga1—Cl4	110.73 (5)	H101—C10—H103	109.5
Cl3—Ga1—Cl4	108.39 (4)	H102—C10—H103	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H103···Cl3	0.97	2.74	3.605 (4)	149
C7—H71···Cl4^ii	0.97	2.78	3.612 (4)	144

Symmetry code: (ii) −x+1, −y+1, −z+1.