Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038792/ez2088sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038792/ez2088Isup2.hkl |
CCDC reference: 660097
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (O-N) = 0.008 Å
- R factor = 0.049
- wR factor = 0.131
- Data-to-parameter ratio = 22.9
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 4.496 Test value = 3.750 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.66 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.26 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 4.50 e/A PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.33 Ratio
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.660 Tmax scaled 0.660 Tmin scaled 0.237
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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
4-Hydroxy piperidine (1 mmol) and trimethyltin chloride (1 mmol) were suspended in dry methanol (150 ml) in a round bottom two necked flask. The mixture was stirred at room temperature. Solid product obtained was filtered off and recrystallized from chloroform to obtain colourless crystals suitable for X-ray analysis (yield 80°; m.p. 59 °C).
Methyl H atoms were included in calculated positions using the riding method, with C—H distances of 0.96 Å, Uiso(H) = 1.5Ueq(C) and torsion angles optimized to give the best fit to the electron density.
The synthesis and structural chemistry of organotin compounds are fertile areas of research because of their extensive biological and pharmaceutical applications (Anderson et al., 1984). The biological applications of organotin compounds as antitumour and anticancer agents (Gielen, 1994; de Vos et al., 1998) have been well documented. We report here the crystal structure of the title compound (I), in a continuation of our efforts in the synthesis and structural characterization of organotin complexes (Shahzadi et al., 2006). The polymeric structure of (I) which contains trigonal bipyramidal Sn atoms is shown in Fig. 1. The Sn atom is bonded to three methyl groups in equatorial positions with Sn—C distances in the range of 2.127 (9)–2.138 (11) Å. In the axial direction, the Sn atom is bonded to a nitrate O atom and a Cl atom. The nitrate N and the Cl atoms each lie on 3-fold axes. The structure forms polymeric sheets parallel to the ab plane, Fig. 1 and 2.
For related literature, see: Anderson et al. (1984); Gielen (1994); Shahzadi et al. (2006); de Vos et al. (1998).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
[Sn3(CH3)9Cl(NO3)] | Dx = 2.114 Mg m−3 |
Mr = 588.84 | Mo Kα radiation, λ = 0.71069 Å |
Trigonal, R3 | Cell parameters from 2484 reflections |
Hall symbol: -R 3 | θ = 2.7–26.4° |
a = 9.843 (4) Å | µ = 4.16 mm−1 |
c = 33.073 (5) Å | T = 100 K |
V = 2775.0 (12) Å3 | Plate, colourless |
Z = 6 | 0.35 × 0.30 × 0.10 mm |
F(000) = 1674 |
Bruker SMART APEX CCD area-detector diffractometer | 1282 independent reflections |
Radiation source: fine-focus sealed tube | 1240 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→12 |
Tmin = 0.360, Tmax = 1.000 | k = −10→12 |
5290 measured reflections | l = −40→36 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0707P)2 + 62.3389P] where P = (Fo2 + 2Fc2)/3 |
1282 reflections | (Δ/σ)max < 0.001 |
56 parameters | Δρmax = 4.50 e Å−3 |
0 restraints | Δρmin = −1.38 e Å−3 |
[Sn3(CH3)9Cl(NO3)] | Z = 6 |
Mr = 588.84 | Mo Kα radiation |
Trigonal, R3 | µ = 4.16 mm−1 |
a = 9.843 (4) Å | T = 100 K |
c = 33.073 (5) Å | 0.35 × 0.30 × 0.10 mm |
V = 2775.0 (12) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 1282 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1240 reflections with I > 2σ(I) |
Tmin = 0.360, Tmax = 1.000 | Rint = 0.040 |
5290 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0707P)2 + 62.3389P] where P = (Fo2 + 2Fc2)/3 |
1282 reflections | Δρmax = 4.50 e Å−3 |
56 parameters | Δρmin = −1.38 e Å−3 |
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.10596 (7) | 0.32791 (9) | 0.08605 (2) | 0.0215 (2) | |
Cl1 | 0.0000 | 0.0000 | 0.06588 (14) | 0.0316 (10) | |
O1 | 0.1849 (8) | 0.5680 (8) | 0.1007 (2) | 0.0246 (14) | |
N1 | 0.3333 | 0.6667 | 0.1019 (4) | 0.025 (3) | |
C1 | −0.1303 (13) | 0.2811 (11) | 0.0814 (3) | 0.031 (2) | |
H1A | −0.1317 | 0.3658 | 0.0674 | 0.046* | |
H1B | −0.1734 | 0.2712 | 0.1080 | 0.046* | |
H1C | −0.1920 | 0.1852 | 0.0667 | 0.046* | |
C2 | 0.1779 (12) | 0.2725 (12) | 0.1413 (3) | 0.023 (2) | |
H2A | 0.2700 | 0.2646 | 0.1367 | 0.035* | |
H2B | 0.0951 | 0.1743 | 0.1514 | 0.035* | |
H2C | 0.2010 | 0.3537 | 0.1608 | 0.035* | |
C3 | 0.2335 (13) | 0.3779 (13) | 0.0307 (3) | 0.027 (2) | |
H3A | 0.3362 | 0.3931 | 0.0359 | 0.041* | |
H3B | 0.2430 | 0.4714 | 0.0189 | 0.041* | |
H3C | 0.1788 | 0.2916 | 0.0123 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0180 (4) | 0.0224 (4) | 0.0251 (3) | 0.0109 (3) | −0.0007 (2) | −0.0006 (2) |
Cl1 | 0.0258 (14) | 0.0258 (14) | 0.043 (2) | 0.0129 (7) | 0.000 | 0.000 |
O1 | 0.015 (3) | 0.015 (3) | 0.043 (4) | 0.007 (3) | 0.001 (3) | −0.002 (3) |
N1 | 0.029 (5) | 0.029 (5) | 0.015 (6) | 0.015 (3) | 0.000 | 0.000 |
C1 | 0.029 (6) | 0.018 (5) | 0.044 (6) | 0.011 (4) | −0.005 (5) | 0.000 (4) |
C2 | 0.020 (5) | 0.020 (5) | 0.031 (5) | 0.010 (4) | −0.003 (4) | −0.003 (4) |
C3 | 0.031 (6) | 0.028 (5) | 0.026 (5) | 0.017 (5) | −0.003 (4) | −0.004 (4) |
Sn1—C2 | 2.127 (9) | C1—H1B | 0.9600 |
Sn1—C3 | 2.134 (10) | C1—H1C | 0.9600 |
Sn1—C1 | 2.138 (11) | C2—H2A | 0.9600 |
Sn1—O1 | 2.142 (7) | C2—H2B | 0.9600 |
Sn1—Cl1 | 2.9298 (13) | C2—H2C | 0.9600 |
O1—N1 | 1.288 (7) | C3—H3A | 0.9600 |
N1—O1i | 1.288 (7) | C3—H3B | 0.9600 |
N1—O1ii | 1.288 (7) | C3—H3C | 0.9600 |
C1—H1A | 0.9600 | ||
C2—Sn1—C3 | 124.3 (4) | H1A—C1—H1B | 109.5 |
C2—Sn1—C1 | 118.2 (4) | Sn1—C1—H1C | 109.5 |
C3—Sn1—C1 | 116.0 (4) | H1A—C1—H1C | 109.5 |
C2—Sn1—O1 | 96.0 (3) | H1B—C1—H1C | 109.5 |
C3—Sn1—O1 | 95.3 (3) | Sn1—C2—H2A | 109.5 |
C1—Sn1—O1 | 90.6 (3) | Sn1—C2—H2B | 109.5 |
C2—Sn1—Cl1 | 83.9 (3) | H2A—C2—H2B | 109.5 |
C3—Sn1—Cl1 | 84.4 (3) | Sn1—C2—H2C | 109.5 |
C1—Sn1—Cl1 | 89.8 (3) | H2A—C2—H2C | 109.5 |
O1—Sn1—Cl1 | 179.64 (19) | H2B—C2—H2C | 109.5 |
N1—O1—Sn1 | 119.2 (4) | Sn1—C3—H3A | 109.5 |
O1i—N1—O1ii | 119.91 (8) | Sn1—C3—H3B | 109.5 |
O1i—N1—O1 | 119.91 (8) | H3A—C3—H3B | 109.5 |
O1ii—N1—O1 | 119.91 (8) | Sn1—C3—H3C | 109.5 |
Sn1—C1—H1A | 109.5 | H3A—C3—H3C | 109.5 |
Sn1—C1—H1B | 109.5 | H3B—C3—H3C | 109.5 |
C2—Sn1—O1—N1 | 71.1 (9) | Sn1—O1—N1—O1i | −11.0 (17) |
C3—Sn1—O1—N1 | −54.3 (9) | Sn1—O1—N1—O1ii | 163.0 (7) |
C1—Sn1—O1—N1 | −170.5 (9) |
Symmetry codes: (i) −y+1, x−y+1, z; (ii) −x+y, −x+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Sn3(CH3)9Cl(NO3)] |
Mr | 588.84 |
Crystal system, space group | Trigonal, R3 |
Temperature (K) | 100 |
a, c (Å) | 9.843 (4), 33.073 (5) |
V (Å3) | 2775.0 (12) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 4.16 |
Crystal size (mm) | 0.35 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.360, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5290, 1282, 1240 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.131, 1.17 |
No. of reflections | 1282 |
No. of parameters | 56 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0707P)2 + 62.3389P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 4.50, −1.38 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
Sn1—C2 | 2.127 (9) | Sn1—O1 | 2.142 (7) |
Sn1—C3 | 2.134 (10) | Sn1—Cl1 | 2.9298 (13) |
Sn1—C1 | 2.138 (11) |
The synthesis and structural chemistry of organotin compounds are fertile areas of research because of their extensive biological and pharmaceutical applications (Anderson et al., 1984). The biological applications of organotin compounds as antitumour and anticancer agents (Gielen, 1994; de Vos et al., 1998) have been well documented. We report here the crystal structure of the title compound (I), in a continuation of our efforts in the synthesis and structural characterization of organotin complexes (Shahzadi et al., 2006). The polymeric structure of (I) which contains trigonal bipyramidal Sn atoms is shown in Fig. 1. The Sn atom is bonded to three methyl groups in equatorial positions with Sn—C distances in the range of 2.127 (9)–2.138 (11) Å. In the axial direction, the Sn atom is bonded to a nitrate O atom and a Cl atom. The nitrate N and the Cl atoms each lie on 3-fold axes. The structure forms polymeric sheets parallel to the ab plane, Fig. 1 and 2.