trans-Di­chlorido­bis­(dimethyl sulfoxide-κO)bis­(4-fluoro­benzyl-κC¹)tin(IV): crystal structure and Hirshfeld surface analysis

The octa­hedrally coordinated Sn^IV atom in [Sn(C₇H₆F)₂Cl₂(C₂H₆OS)₂] is located on a centre of inversion so the resulting donor C₂Cl₂O₂ donor set is all-trans. The three-dimensional mol­ecular packing is sustained by C—H...F, C—H...Cl and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.046
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5 Report

Alert level G
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00010 Ang.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Sn     --  Cl1     ..        8.0 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         56 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Note

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

   0 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
   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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

trans-Dichloridobis(dimethyl sulfoxide-κO)bis(4-fluorobenzyl-κC¹)tin(IV)

Crystal data

[Sn(C7H6F)2Cl2(C2H6OS)2]	F(000) = 564
Mr = 564.08	Dx = 1.675 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 8.2363 (1) Å	Cell parameters from 6127 reflections
b = 12.7020 (2) Å	θ = 5.4–76.3°
c = 11.4038 (1) Å	µ = 13.28 mm^−1
β = 110.391 (2)°	T = 100 K
V = 1118.28 (3) Å^3	Prism, colourless
Z = 2	0.24 × 0.12 × 0.10 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, AtlasS2 diffractometer	2292 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	2228 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
ω scans	θmax = 76.5°, θmin = 5.4°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	h = −10→9
Tmin = 0.636, Tmax = 1.000	k = −15→15
7792 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.018	H-atom parameters constrained
wR(F^2) = 0.046	w = 1/[σ^2(Fo^2) + (0.0233P)^2 + 0.7527P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2292 reflections	Δρmax = 0.35 e Å^−3
126 parameters	Δρmin = −0.76 e Å^−3

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
Sn	0.5000	0.5000	0.5000	0.00673 (6)
Cl1	0.44665 (6)	0.48762 (3)	0.26545 (4)	0.01508 (10)
S1	0.55778 (5)	0.24628 (3)	0.43015 (3)	0.00881 (9)
F1	0.06456 (15)	0.03219 (9)	0.34347 (11)	0.0248 (2)
O1	0.60349 (15)	0.33583 (9)	0.52752 (10)	0.0106 (2)
C1	0.2332 (2)	0.45714 (13)	0.46551 (16)	0.0130 (3)
H1A	0.2054	0.4746	0.5410	0.016*
H1B	0.1583	0.5013	0.3962	0.016*
C2	0.1878 (2)	0.34437 (13)	0.43339 (15)	0.0098 (3)
C3	0.1093 (2)	0.31260 (13)	0.30871 (15)	0.0111 (3)
H3	0.0838	0.3637	0.2440	0.013*
C4	0.0679 (2)	0.20772 (14)	0.27783 (15)	0.0134 (3)
H4	0.0147	0.1868	0.1930	0.016*
C5	0.1058 (2)	0.13487 (13)	0.37280 (16)	0.0140 (3)
C6	0.1822 (2)	0.16192 (14)	0.49747 (16)	0.0144 (3)
H6	0.2062	0.1101	0.5613	0.017*
C7	0.2229 (2)	0.26727 (14)	0.52668 (15)	0.0121 (3)
H7	0.2758	0.2873	0.6118	0.014*
C8	0.6371 (2)	0.13286 (13)	0.52466 (15)	0.0154 (3)
H8A	0.7576	0.1447	0.5786	0.023*
H8B	0.6312	0.0718	0.4708	0.023*
H8C	0.5662	0.1197	0.5766	0.023*
C9	0.7181 (2)	0.25482 (14)	0.35875 (16)	0.0159 (3)
H9A	0.7035	0.3209	0.3118	0.024*
H9B	0.7055	0.1952	0.3017	0.024*
H9C	0.8335	0.2530	0.4235	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.00785 (9)	0.00543 (9)	0.00565 (8)	0.00005 (4)	0.00078 (6)	−0.00080 (4)
Cl1	0.0208 (2)	0.0153 (2)	0.00719 (18)	0.00143 (14)	0.00249 (16)	0.00013 (13)
S1	0.00860 (18)	0.00802 (18)	0.00877 (16)	0.00079 (13)	0.00171 (14)	−0.00157 (13)
F1	0.0250 (6)	0.0089 (5)	0.0328 (6)	−0.0026 (4)	0.0006 (5)	−0.0014 (5)
O1	0.0135 (6)	0.0067 (5)	0.0095 (5)	0.0016 (4)	0.0012 (4)	−0.0021 (4)
C1	0.0082 (7)	0.0131 (9)	0.0172 (8)	−0.0007 (6)	0.0039 (6)	−0.0030 (6)
C2	0.0059 (7)	0.0112 (8)	0.0122 (7)	0.0000 (6)	0.0032 (6)	−0.0012 (6)
C3	0.0087 (7)	0.0129 (8)	0.0105 (7)	0.0005 (6)	0.0018 (6)	0.0023 (6)
C4	0.0115 (8)	0.0152 (9)	0.0117 (7)	−0.0004 (6)	0.0020 (6)	−0.0028 (6)
C5	0.0110 (8)	0.0078 (8)	0.0211 (8)	−0.0014 (6)	0.0030 (6)	−0.0018 (6)
C6	0.0117 (8)	0.0151 (8)	0.0152 (8)	0.0015 (6)	0.0032 (6)	0.0065 (6)
C7	0.0089 (8)	0.0176 (8)	0.0090 (7)	−0.0006 (6)	0.0022 (6)	0.0000 (6)
C8	0.0228 (9)	0.0080 (8)	0.0141 (8)	0.0027 (6)	0.0049 (7)	0.0002 (6)
C9	0.0166 (9)	0.0175 (9)	0.0167 (8)	0.0005 (6)	0.0097 (7)	−0.0019 (6)

Geometric parameters (Å, º)

Sn—C1	2.1628 (16)	C3—C4	1.390 (2)
Sn—C1^i	2.1628 (16)	C3—H3	0.9500
Sn—O1	2.2332 (11)	C4—C5	1.375 (2)
Sn—O1^i	2.2332 (11)	C4—H4	0.9500
Sn—Cl1^i	2.5599 (4)	C5—C6	1.383 (2)
Sn—Cl1	2.5599 (4)	C6—C7	1.392 (2)
S1—O1	1.5417 (11)	C6—H6	0.9500
S1—C9	1.7796 (17)	C7—H7	0.9500
S1—C8	1.7815 (17)	C8—H8A	0.9800
F1—C5	1.360 (2)	C8—H8B	0.9800
C1—C2	1.494 (2)	C8—H8C	0.9800
C1—H1A	0.9900	C9—H9A	0.9800
C1—H1B	0.9900	C9—H9B	0.9800
C2—C7	1.400 (2)	C9—H9C	0.9800
C2—C3	1.401 (2)
C1—Sn—C1^i	180.0	C4—C3—C2	121.27 (15)
C1—Sn—O1	95.99 (5)	C4—C3—H3	119.4
C1—Sn—Cl1	90.05 (5)	C2—C3—H3	119.4
C1—Sn—Cl1^i	89.95 (5)	C5—C4—C3	118.50 (15)
C1—Sn—O1^i	84.01 (5)	C5—C4—H4	120.8
C1—Sn—Cl1^i	89.95 (5)	C3—C4—H4	120.8
O1—Sn—Cl1	90.44 (3)	F1—C5—C4	118.88 (15)
O1—Sn—Cl1^i	89.56 (3)	F1—C5—C6	118.46 (15)
C1^i—Sn—O1	84.01 (5)	C4—C5—C6	122.66 (16)
C1^i—Sn—O1^i	95.99 (5)	C5—C6—C7	118.07 (15)
O1—Sn—O1^i	180.0	C5—C6—H6	121.0
C1^i—Sn—Cl1^i	90.05 (5)	C7—C6—H6	121.0
O1^i—Sn—Cl1^i	90.44 (3)	C6—C7—C2	121.47 (15)
O1^i—Sn—Cl1	89.56 (3)	C6—C7—H7	119.3
Cl1^i—Sn—Cl1	180.000 (18)	C2—C7—H7	119.3
O1—S1—C9	104.51 (8)	S1—C8—H8A	109.5
O1—S1—C8	102.41 (7)	S1—C8—H8B	109.5
C9—S1—C8	98.73 (8)	H8A—C8—H8B	109.5
S1—O1—Sn	127.03 (6)	S1—C8—H8C	109.5
C2—C1—Sn	115.97 (11)	H8A—C8—H8C	109.5
C2—C1—H1A	108.3	H8B—C8—H8C	109.5
Sn—C1—H1A	108.3	S1—C9—H9A	109.5
C2—C1—H1B	108.3	S1—C9—H9B	109.5
Sn—C1—H1B	108.3	H9A—C9—H9B	109.5
H1A—C1—H1B	107.4	S1—C9—H9C	109.5
C7—C2—C3	118.03 (15)	H9A—C9—H9C	109.5
C7—C2—C1	121.12 (14)	H9B—C9—H9C	109.5
C3—C2—C1	120.85 (15)
C9—S1—O1—Sn	92.64 (10)	C3—C4—C5—F1	179.52 (15)
C8—S1—O1—Sn	−164.80 (9)	C3—C4—C5—C6	0.4 (3)
Sn—C1—C2—C7	81.29 (17)	F1—C5—C6—C7	−179.60 (15)
Sn—C1—C2—C3	−98.42 (16)	C4—C5—C6—C7	−0.5 (3)
C7—C2—C3—C4	−0.3 (2)	C5—C6—C7—C2	0.1 (3)
C1—C2—C3—C4	179.42 (15)	C3—C2—C7—C6	0.2 (2)
C2—C3—C4—C5	0.0 (2)	C1—C2—C7—C6	−179.50 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F1^ii	0.95	2.49	3.333 (2)	147
C6—H6···Cl1^iii	0.95	2.77	3.6129 (18)	148
C8—H8B···Cl1^iv	0.98	2.76	3.6379 (17)	150
C9—H9C···Cg1^v	0.98	2.67	3.3887 (19)	130

Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x, −y−1/2, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x+1, y, z.