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The title compound, [Sn4(CH3)8(C13H8Cl2NO2)2(C2H5O)2O2], is a centrosymmetric dimer, with three linearly fused four-membered Sn—O—Sn—O rings. The coordination poly­hedron of the Sn atom bonded to the carboxyl­ate can be described as trigonal–bipyramidal distorted toward square-pyramidal. That of the second Sn atom is similar, but the distortion towards square-pyramidal geometry is greater. The Sn—O and Sn—C distances are 2.020 (2)–2.226 (2) and 2.096 (4)–2.114 (4) Å, respectively. The benzene rings of the 2-[(2,3-dichloro­phenyl)­amino]benzoate ligand subtend an angle of 50.49 (17)°; the conformation of the ligand is stabilized by intra­molecular N—H...Cl and N—H...O hydrogen bonds. The structure is assembled via π–π stacking inter­actions to form chains parallel to [1\overline{2}0].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105025989/jz1743sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105025989/jz1743Isup2.hkl
Contains datablock I

CCDC reference: 187212

Comment top

2-[(2,3-Dichlorophenyl)amino]benzoic acid is a member of the class of non-steroidal anti-inflammatory drugs (NSAIDs). All NSAIDs are derivatives of N-phenylanthranilic acid and many of them are frequently used in medicine (Dokorou et al., 2001;), e.g. as analgesics, anti-inflammatories and antipyretics, because they have fewer side effects of sedation, respiratory depression or addiction than other pharmaceuticals with similar properties, such as steroids (Berner et al., 1970; Vedres et al., 1973; Bauman et al., 2005). NSAIDs inhibit cyclooxygenase (COX) activity and in consequence depress the synthesis of prostaglandins (Insel, 1996; Lands & Hanel, 1983; Reynolds et al., 1993). They have also been used in combination with cytotoxic drugs (Thicher et al., 1994, Gomez-Gaviro et al., 2002). At non-toxic levels, they significantly increase the cytotoxicity of the anthracyclines doxorubicin, daunorubicin, epirubicin, teniposide, VP-16 and vincristine (Duffy et al., 1998). 2-[(2,3-Dichlorophenyl)amino]benzoic acid can be considered as an analogue of tolfenamic and flufenamic acids and other clinically used fenamates (Kovala-Demertzi et al., 2001).

Organotin(IV) carboxylates are an important class of compounds that have very varied applications, from catalysis to biocides (antifouling agents) and as wood preservatives (Davies, 2004; Smith, 1998). However, applications of tin compounds are often limited because of their high toxicity, e.g. antifouling paints (WS Atkins International Ltd., 1998). Tin–organic compounds have also shown antitumour activity (Gielen, 1989). Thus, combining in one compound the pharmacologically important 2-[(2,3-dichlorophenyl)amino]benzoate ligand and potentially biologically active organotin moieties could lead to compounds with interesting properties and applications. We have therefore synthesized the title compound, (I), and present its crystal structure here.

A perspective view of the title compound (I) is shown in Fig. 1. A l l interatomic distances between non-metal atoms can be considered normal. The structure is composed of a centrosymmetric dimer, with three four-membered Sn—O—Sn—O rings in a linearly fused arrangement.

In the Cambridge Structural Database (CSD, Version 5.25; Allen, 2002), 108 compounds can be found containing the (Sn2O2)3 ring system. In 81 of them there are additional geometrical constraints imposed by chelating or bridging substituents; thus, a comparison of geometries was performed for only 27 compounds (CSD refcodes ASUJED, BEKDAX, CATGOT, CATGUZ, EKAMUY, EKANAF, HUTYIE, HUTYIE, LIRNUV, MASYOU, MOQXOF, NIVXEV, NUZMIE, OLONIM, QASMIG, QAYNOT, QAYNUZ, QIZREW, QOHPUY, QOHQAF, RACFOQ, ROGJIG, TIPSNB, UBIFOA, VOFDAV, XAKSAD, YELRAI, ZABPIB). Except for CATGUZ, in all these compounds the central ring (Sn2O2) is ideally planar; in CATGUZ the atoms deviate by only 0.04 Å from the mass-weighted least-squares plane of the ring. The peripheral rings are close to planarity in all compounds; the maximum deviation is 0.085 Å for compound TIPSNB. The interplanar angle between the central ring and the peripheral rings varies from 0.58° (QAYNOT) to 5.61° (MOQXOF).

In (I), the mass-weighted least-squares plane of the Sn1/O3/Sn2/O4 ring is slightly distorted from planarity [the largest deviation is 0.0665 (10) Å for atom O3] and subtends an angle of 7.62 (17)° with the central Sn1/O3/Sn1i/O3i ring, which is planar by symmetry [symmetry code: (i) 1 − x, −y, −z]. The overall arrangement of the central unit is closely similar to those previously reported for bis(3-(4-methylcoumarinyl-7-oxy)(µ2-methoxy)- 1,1,3,3-tetramethyl-distannoxane) (Zhang et al., 2003; CSD refcode OLONIM), bis[[(µ3-oxo)(µ2-(1,4-oxazin-4-yl)carbonylthioacetato]- [(1,4-oxazin-4-yl)carbonylthioacetato]-tetra-n-butyl-ditin] [Please check nesting of brackets] ethanol solvate (Ng et al., 2000; CSD refcode QASMIG), and bis[bis(di-n-butyl)(µ3-oxo)(µ2-2-methoxyphenoxo-O,O)- (2-methoxyphenoxy-O)-di-tin] (Vatsa et al., 1991; CSD refcode: VOFDAV).

The coordination polyhedron of Sn2 can be described as trigonal–bipyramidal [atoms O1 and O4 axial, and atoms O3, C16 and C17 equatorial; sum of the squares of the deviations from ideal angles Σσ(Φ) = 1514°2 (Favas & Kepert, 1980)] distorted toward a tetragonal pyramid [atom O3 apical, and atoms O1, O4, C16 and C17 basal; Σσ(Φ) = 5326°2]. The coordination polyhedron around atom Sn1 is more distorted towards square-pyramidal but can be described in the same general way [trigonal–bipyramidal with atoms O4 and O3i axial, and atoms O3, C14 and C15 equatorial, Σσ(Φ) = 1917°2, or square-pyramidal with atom O3 apical, and atoms O3i, O4, C14 and C15 basal, Σσ(Φ) = 4860°2]. The major deformations originate from constraints imposed by the rigid four-membered Sn2O2 rings.

The benzene rings of the 2-[(2,3-dichlorophenyl)amino]benzoate ligand subtend an angle of 50.49 (17)°. The carboxylic acid group makes an angle of 12.3 (5)° with its parent aromatic ring. The C1—C7—O1—Sn2 torsion angle is 177.5 (2)°. The conformation of the ligand is stabilized by intramolecular N—H···Cl and N—H···O hydrogen bonds involving the same H atom (Table 2, Fig. 1). The packing further involves ππ stacking interactions (Hunter & Sanders, 1990) between pairs of adjacent Cl-bearing aromatic rings [symmetry code: 2 − x, −y − 1, −z; ring centroid distance 3.929 (6) Å, perpendicular distance between symmetry-parallel rings 3.504 (6) Å, angle between the vector linking ring centroids and the normal to one plane 26.9 (3)°, offset 1.777 (6) Å]. Via these interactions, a π-bonded chain is created parallel to [120].

Experimental top

The title compound was prepared according to the method of Dokorou (2005). The crystals used for data collection were grown from an ethanol solution by slow evaporation.

Refinement top

All C-bound H atoms were placed in calculated positions and were refined as riding on their adjacent C atom, with C—H distances in the range 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(Cnon-methyl) or 1.5Ueq(Cmethyl)]. The methyl groups were allowed to rotate about their local threefold axis (AFIX 137). The N-bound H atom was found in the difference Fourier synthesis and was refined as riding on its parent N atom at an N—H distance of 0.92 Å, with the isotropic displacement parameter free to refine. [Please check added distances]

Computing details top

Data collection: CrysAlis CCD (UNIL IC and Kuma, 2000); cell refinement: CrysAlis RED (UNIL IC and Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows (version 1.062; Farrugia 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1]
[Figure 2]
Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms of the methyl and ethyl groups have been omitted for clarity. Intramolecular hydrogen bonds are indicated by dashed lines.
{2-[(2,3-Dichlorophenyl)amino]benzoato-κO}di-µ2-ethoxo-octamethyldi- µ3-oxo-tetratin(IV) top
Crystal data top
[Sn4(CH3)8(C13H8Cl2NO2)2(C2H5O)2O2]F(000) = 1248
Mr = 1279.36Dx = 1.785 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 14.0875 (6) ÅCell parameters from 6140 reflections
b = 9.7613 (4) Åθ = 2–20°
c = 17.5858 (8) ŵ = 2.35 mm1
β = 100.106 (3)°T = 291 K
V = 2380.74 (18) Å3Needle, orange
Z = 20.53 × 0.07 × 0.07 mm
Data collection top
Kuma KM4 CCD area-detector
diffractometer
4230 independent reflections
Radiation source: fine-focus sealed tube3656 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 25.1°, θmin = 3.4°
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
h = 1616
Tmin = 0.518, Tmax = 0.894k = 1011
27541 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: diffmap
wR(F2) = 0.063H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0294P)2 + 0.8584P]
where P = (Fo2 + 2Fc2)/3
4230 reflections(Δ/σ)max = 0.001
259 parametersΔρmax = 1.10 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
[Sn4(CH3)8(C13H8Cl2NO2)2(C2H5O)2O2]V = 2380.74 (18) Å3
Mr = 1279.36Z = 2
Monoclinic, P21/nMo Kα radiation
a = 14.0875 (6) ŵ = 2.35 mm1
b = 9.7613 (4) ÅT = 291 K
c = 17.5858 (8) Å0.53 × 0.07 × 0.07 mm
β = 100.106 (3)°
Data collection top
Kuma KM4 CCD area-detector
diffractometer
4230 independent reflections
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
3656 reflections with I > 2σ(I)
Tmin = 0.518, Tmax = 0.894Rint = 0.036
27541 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.15Δρmax = 1.10 e Å3
4230 reflectionsΔρmin = 0.50 e Å3
259 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Sn10.471301 (17)0.03647 (2)0.085414 (14)0.03253 (8)
O30.55398 (17)0.0917 (2)0.03312 (13)0.0367 (6)
O40.53620 (19)0.1049 (3)0.17197 (14)0.0426 (6)
Sn20.608001 (18)0.24902 (2)0.102016 (14)0.03517 (8)
C10.7400 (3)0.4772 (4)0.0642 (2)0.0396 (9)
C20.7974 (3)0.5958 (4)0.0615 (2)0.0441 (9)
C30.8211 (3)0.6448 (5)0.1307 (3)0.0591 (12)
H30.85760.72430.13000.071*
C40.7918 (4)0.5788 (5)0.1986 (3)0.0650 (13)
H40.80810.61400.24380.078*
C50.7385 (4)0.4606 (5)0.2016 (3)0.0635 (13)
H50.71970.41480.24820.076*
C60.7130 (3)0.4107 (5)0.1347 (2)0.0532 (11)
H60.67680.33070.13680.064*
N10.8241 (3)0.6661 (4)0.0071 (2)0.0551 (9)
H1N0.78520.65620.04350.061 (13)*
C80.9060 (3)0.7469 (4)0.0284 (2)0.0445 (10)
C90.9049 (3)0.8484 (4)0.0842 (2)0.0403 (9)
C100.9864 (3)0.9260 (4)0.1103 (2)0.0493 (10)
C111.0694 (3)0.9083 (5)0.0809 (3)0.0634 (13)
H111.12310.96310.09740.076*
C121.0716 (3)0.8076 (5)0.0265 (3)0.0658 (13)
H121.12790.79330.00680.079*
C130.9917 (3)0.7275 (5)0.0004 (3)0.0584 (12)
H130.99510.65980.03620.070*
Cl10.80140 (8)0.87167 (13)0.12217 (7)0.0619 (3)
Cl20.98415 (9)1.05157 (14)0.17976 (8)0.0743 (4)
C70.7039 (3)0.4257 (4)0.0053 (2)0.0427 (9)
O10.66257 (19)0.3075 (3)0.00124 (15)0.0471 (7)
O20.7110 (2)0.4937 (3)0.06478 (17)0.0583 (8)
C140.3271 (3)0.0202 (5)0.0867 (3)0.0549 (11)
H14A0.31300.10450.05890.082*
H14B0.28470.05040.06280.082*
H14C0.31810.03240.13920.082*
C150.5441 (3)0.2151 (4)0.1320 (3)0.0582 (12)
H15A0.59850.18980.17030.087*
H15B0.50100.27090.15530.087*
H15C0.56580.26570.09150.087*
C160.5010 (3)0.3983 (5)0.1015 (3)0.0644 (13)
H16A0.43880.35810.08400.097*
H16B0.50390.43350.15280.097*
H16C0.51120.47150.06740.097*
C170.7414 (3)0.2255 (5)0.1761 (3)0.0644 (13)
H17A0.79220.22350.14620.097*
H17B0.75150.30100.21160.097*
H17C0.74150.14130.20430.097*
C180.5096 (4)0.1322 (5)0.2448 (2)0.0657 (13)
H18A0.53610.22020.26350.079*
H18B0.44000.13840.23830.079*
C190.5436 (5)0.0270 (6)0.3027 (3)0.095 (2)
H19A0.61260.02110.30990.143*
H19B0.52450.05090.35080.143*
H19C0.51600.05980.28530.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03505 (14)0.02918 (14)0.03465 (14)0.00643 (10)0.00966 (10)0.00158 (10)
O30.0429 (14)0.0338 (13)0.0355 (13)0.0155 (11)0.0126 (11)0.0084 (11)
O40.0581 (17)0.0379 (14)0.0340 (14)0.0146 (13)0.0142 (12)0.0090 (11)
Sn20.03702 (15)0.02837 (14)0.04002 (15)0.00708 (10)0.00652 (11)0.00750 (11)
C10.036 (2)0.038 (2)0.047 (2)0.0020 (17)0.0116 (17)0.0004 (18)
C20.050 (2)0.036 (2)0.049 (2)0.0044 (18)0.0135 (19)0.0023 (18)
C30.075 (3)0.051 (3)0.056 (3)0.014 (2)0.023 (2)0.005 (2)
C40.082 (3)0.071 (3)0.046 (3)0.010 (3)0.023 (2)0.003 (2)
C50.078 (3)0.073 (3)0.041 (2)0.015 (3)0.016 (2)0.013 (2)
C60.052 (3)0.055 (3)0.054 (3)0.011 (2)0.012 (2)0.010 (2)
N10.069 (2)0.052 (2)0.050 (2)0.0281 (19)0.0238 (18)0.0087 (18)
C80.047 (2)0.040 (2)0.047 (2)0.0107 (18)0.0113 (19)0.0054 (18)
C90.039 (2)0.041 (2)0.040 (2)0.0067 (17)0.0059 (16)0.0084 (17)
C100.049 (2)0.046 (2)0.050 (2)0.0079 (19)0.0000 (19)0.0020 (19)
C110.042 (3)0.071 (3)0.075 (3)0.011 (2)0.004 (2)0.000 (3)
C120.042 (3)0.076 (3)0.083 (4)0.002 (2)0.020 (2)0.011 (3)
C130.065 (3)0.049 (3)0.065 (3)0.001 (2)0.020 (2)0.000 (2)
Cl10.0511 (6)0.0751 (8)0.0623 (7)0.0134 (6)0.0182 (5)0.0153 (6)
Cl20.0695 (8)0.0776 (9)0.0724 (8)0.0205 (7)0.0028 (6)0.0250 (7)
C70.037 (2)0.042 (2)0.050 (2)0.0080 (17)0.0104 (18)0.0017 (19)
O10.0566 (17)0.0371 (15)0.0507 (16)0.0180 (13)0.0180 (13)0.0050 (13)
O20.078 (2)0.0546 (18)0.0481 (17)0.0291 (16)0.0268 (15)0.0146 (15)
C140.040 (2)0.072 (3)0.054 (3)0.002 (2)0.013 (2)0.006 (2)
C150.058 (3)0.043 (2)0.070 (3)0.000 (2)0.002 (2)0.004 (2)
C160.064 (3)0.055 (3)0.076 (3)0.012 (2)0.017 (2)0.004 (3)
C170.048 (3)0.072 (3)0.068 (3)0.008 (2)0.005 (2)0.003 (3)
C180.093 (4)0.062 (3)0.045 (3)0.016 (3)0.020 (2)0.015 (2)
C190.142 (6)0.094 (4)0.050 (3)0.014 (4)0.018 (3)0.011 (3)
Geometric parameters (Å, º) top
Sn1—O32.036 (2)C9—Cl11.722 (4)
Sn1—C142.109 (4)C10—C111.370 (6)
Sn1—C152.114 (4)C10—Cl21.734 (4)
Sn1—O3i2.122 (2)C11—C121.376 (7)
Sn1—O42.137 (2)C11—H110.9300
O3—Sn1i2.122 (2)C12—C131.381 (6)
Sn2—O32.020 (2)C12—H120.9300
O4—C181.421 (5)C13—H130.9300
Sn2—O42.226 (2)C7—O21.229 (5)
Sn2—C162.096 (4)C7—O11.289 (4)
Sn2—C172.103 (4)C14—H14A0.9600
Sn2—O12.169 (3)C14—H14B0.9600
C1—C61.393 (5)C14—H14C0.9600
C1—C21.409 (5)C15—H15A0.9600
C1—C71.490 (5)C15—H15B0.9600
C2—N11.380 (5)C15—H15C0.9600
C2—C31.401 (6)C16—H16A0.9600
C3—C41.357 (6)C16—H16B0.9600
C3—H30.9300C16—H16C0.9600
C4—C51.373 (6)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C5—C61.377 (6)C17—H17C0.9600
C5—H50.9300C18—C191.466 (7)
C6—H60.9300C18—H18A0.9700
N1—C81.394 (5)C18—H18B0.9700
N1—H1N0.9187C19—H19A0.9600
C8—C131.393 (6)C19—H19B0.9600
C8—C91.396 (5)C19—H19C0.9600
C9—C101.385 (5)
O3—Sn1—C14118.17 (15)C11—C10—C9121.2 (4)
O3—Sn1—C15113.89 (15)C11—C10—Cl2118.5 (3)
C14—Sn1—C15127.94 (18)C9—C10—Cl2120.3 (3)
O3—Sn1—O3i73.92 (10)C10—C11—C12118.6 (4)
C14—Sn1—O3i94.68 (13)C10—C11—H11120.7
C15—Sn1—O3i99.06 (15)C12—C11—H11120.7
O3—Sn1—O473.61 (9)C11—C12—C13121.2 (4)
C14—Sn1—O496.61 (14)C11—C12—H12119.4
C15—Sn1—O497.98 (14)C13—C12—H12119.4
O3i—Sn1—O4147.22 (9)C12—C13—C8120.8 (4)
Sn2—O3—Sn1112.42 (11)C12—C13—H13119.6
Sn2—O3—Sn1i139.72 (12)C8—C13—H13119.6
Sn1—O3—Sn1i106.08 (10)O2—C7—O1121.9 (4)
C18—O4—Sn1128.0 (2)O2—C7—C1121.8 (3)
C18—O4—Sn2126.6 (2)O1—C7—C1116.3 (3)
Sn1—O4—Sn2101.16 (10)C7—O1—Sn2112.5 (2)
O3—Sn2—C16109.31 (16)Sn1—C14—H14A109.5
O3—Sn2—C17119.36 (15)Sn1—C14—H14B109.5
C16—Sn2—C17129.99 (19)H14A—C14—H14B109.5
O3—Sn2—O181.33 (9)Sn1—C14—H14C109.5
C16—Sn2—O1100.01 (15)H14A—C14—H14C109.5
C17—Sn2—O197.92 (16)H14B—C14—H14C109.5
O3—Sn2—O472.00 (9)Sn1—C15—H15A109.5
C16—Sn2—O492.61 (15)Sn1—C15—H15B109.5
C17—Sn2—O491.84 (15)H15A—C15—H15B109.5
O1—Sn2—O4153.04 (9)Sn1—C15—H15C109.5
C6—C1—C2118.6 (4)H15A—C15—H15C109.5
C6—C1—C7119.6 (4)H15B—C15—H15C109.5
C2—C1—C7121.8 (3)Sn2—C16—H16A109.5
N1—C2—C3121.3 (4)Sn2—C16—H16B109.5
N1—C2—C1120.3 (4)H16A—C16—H16B109.5
C3—C2—C1118.3 (4)Sn2—C16—H16C109.5
C4—C3—C2121.4 (4)H16A—C16—H16C109.5
C4—C3—H3119.3H16B—C16—H16C109.5
C2—C3—H3119.3Sn2—C17—H17A109.5
C3—C4—C5120.8 (4)Sn2—C17—H17B109.5
C3—C4—H4119.6H17A—C17—H17B109.5
C5—C4—H4119.6Sn2—C17—H17C109.5
C4—C5—C6119.2 (4)H17A—C17—H17C109.5
C4—C5—H5120.4H17B—C17—H17C109.5
C6—C5—H5120.4O4—C18—C19112.9 (4)
C5—C6—C1121.7 (4)O4—C18—H18A109.0
C5—C6—H6119.2C19—C18—H18A109.0
C1—C6—H6119.2O4—C18—H18B109.0
C2—N1—C8127.0 (4)C19—C18—H18B109.0
C2—N1—H1N116.8H18A—C18—H18B107.8
C8—N1—H1N116.1C18—C19—H19A109.5
C13—C8—N1123.7 (4)C18—C19—H19B109.5
C13—C8—C9117.5 (4)H19A—C19—H19B109.5
N1—C8—C9118.7 (4)C18—C19—H19C109.5
C10—C9—C8120.7 (4)H19A—C19—H19C109.5
C10—C9—Cl1120.5 (3)H19B—C19—H19C109.5
C8—C9—Cl1118.7 (3)
C1—C7—O1—Sn2177.5 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl10.922.512.908 (4)107
N1—H1N···O20.921.972.639 (4)128

Experimental details

Crystal data
Chemical formula[Sn4(CH3)8(C13H8Cl2NO2)2(C2H5O)2O2]
Mr1279.36
Crystal system, space groupMonoclinic, P21/n
Temperature (K)291
a, b, c (Å)14.0875 (6), 9.7613 (4), 17.5858 (8)
β (°) 100.106 (3)
V3)2380.74 (18)
Z2
Radiation typeMo Kα
µ (mm1)2.35
Crystal size (mm)0.53 × 0.07 × 0.07
Data collection
DiffractometerKuma KM4 CCD area-detector
diffractometer
Absorption correctionNumerical
(X-RED; Stoe & Cie, 1999)
Tmin, Tmax0.518, 0.894
No. of measured, independent and
observed [I > 2σ(I)] reflections
27541, 4230, 3656
Rint0.036
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.063, 1.15
No. of reflections4230
No. of parameters259
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.10, 0.50

Computer programs: CrysAlis CCD (UNIL IC and Kuma, 2000), CrysAlis RED (UNIL IC and Kuma, 2000), CrysAlis RED, SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows (version 1.062; Farrugia 1997), SHELXL97.

Selected geometric parameters (Å, º) top
Sn1—O32.036 (2)Sn2—O32.020 (2)
Sn1—C142.109 (4)Sn2—O42.226 (2)
Sn1—C152.114 (4)Sn2—C162.096 (4)
Sn1—O3i2.122 (2)Sn2—C172.103 (4)
Sn1—O42.137 (2)Sn2—O12.169 (3)
O3—Sn1—C14118.17 (15)O3—Sn2—C16109.31 (16)
O3—Sn1—C15113.89 (15)O3—Sn2—C17119.36 (15)
C14—Sn1—C15127.94 (18)C16—Sn2—C17129.99 (19)
O3—Sn1—O3i73.92 (10)O3—Sn2—O181.33 (9)
C14—Sn1—O3i94.68 (13)C16—Sn2—O1100.01 (15)
C15—Sn1—O3i99.06 (15)C17—Sn2—O197.92 (16)
O3—Sn1—O473.61 (9)O3—Sn2—O472.00 (9)
C14—Sn1—O496.61 (14)C16—Sn2—O492.61 (15)
C15—Sn1—O497.98 (14)C17—Sn2—O491.84 (15)
O3i—Sn1—O4147.22 (9)O1—Sn2—O4153.04 (9)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl10.922.512.908 (4)107
N1—H1N···O20.921.972.639 (4)128
 

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