Acta Cryst.(2002). E58, m661±m662 DOI: 10.1107/S1600536802019001 Chee, Lo and Ng [Sn(C2F3O2)(C6H5)3(H2O)]C18H12N6
m661
metal-organic papers
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
Aquatriphenyl(trifluoroacetato)tin±
2,4,6-tris(2-pyridyl)-1,3,5-triazine (1/1)
Chin Fei Chee, Kong Mun Lo and Seik Weng Ng*
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my
Key indicators Single-crystal X-ray study
T= 168 K
Mean(C±C) = 0.006 AÊ
Rfactor = 0.040
wRfactor = 0.095
Data-to-parameter ratio = 14.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
The water-coordinated Sn atom in the title compound, [Sn(C2F3O2)(C6H5)3(H2O)]C18H12N6, forms hydrogen bonds
to two of the pyridyl N atoms of theN-heterocycle [Owater N
= 2.841 (4) and 2.826 (4) AÊ]. The Sn atom showstrans-C3SnO2
trigonal bipyramidal coordination.
Comment
TheN-heterocycle 2,4,6-tris(2-pyridyl)-1,3,5-triazine interacts with the Lewis acceptor bis(triphenyltin) succinate through the coordinated water molecules in the centrosymmetric adduct [Sn Owater= 2.487 (3) AÊ in the monoclinic
modi®-cation and 2.441 (3) AÊ in the triclinic modi®modi®-cation]. The water molecule forms hydrogen bonds to the N atoms of the pyridyl rings [Owater N = 2.921 (5) and 2.999 (5) AÊ in the monoclinic
modi®cation, and 2.860 (5) and 2.907 (5) AÊ in the triclinic modi®cation] (Ng, 1998). In the the 1/1 adduct, (I), of the same triazine with with triphenyltin tri¯uoroacetate monohydrate (Fig. 1), a similar hydrogen-bonding scheme is also noted [Owater N = 2.841 (4) and 2.826 (4) AÊ].
The water donor occupies an apical position of thetrans -C3SnO2 trigonal bipyramidal polyhedron of the Sn atom;
owing to the electron-withdrawing capacity of the tri¯uro-methyl group, the Lewis acidity of the triphenyltin acceptor is enhanced, and this leads to a shortening of the SnÐOwater
bond [Sn O = 2.311 (3) AÊ]. The bond distance is similar to that [2.335 (4) AÊ] found in bis[aquatri¯uoroacetatotriphenyl-tin±1,10-phenanthroline] (Ng et al., 1996); however, this compound features a different hydrogen-bonding scheme.
Experimental
The compound was prepared by heating triphenyltin hydroxide, tri-¯uoroacetic acid and 2,4,6-tris(2-pyridyl)-1,3,5-triazine in a 1:1:1 molar ratio in toluene for 1 h. The product separated as light-yellow cubic blocks when the solvent was removed (m.p. 445±447 K).
Crystal data
[Sn(C2F3O2)(C6H5)3
-(H2O)]C18H12N6
Mr= 793.36
Triclinic,P1
a= 10.567 (1) AÊ
b= 11.053 (1) AÊ
c= 15.438 (1) AÊ
= 105.559 (2) = 97.496 (2) = 101.637 (2) V= 1668.5 (2) AÊ3
Z= 2
Dx= 1.58 Mg mÿ3
MoKradiation Cell parameters from 7791
re¯ections
= 2.0±26.4 = 0.83 mmÿ1
T= 168 (2) K Block, light yellow 0.300.190.10 mm
Data collection
Bruker CCD area-detector diffractometer
!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin= 0.789,Tmax= 0.922
21865 measured re¯ections
6720 independent re¯ections 5013 re¯ections withI> 2(I)
Rint= 0.063
max= 26.4
h=ÿ13!13
k=ÿ13!7
l=ÿ19!19
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.040
wR(F2) = 0.095
S= 0.93 6720 re¯ections 468 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.0525P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 1.43 e AÊÿ3
min=ÿ1.49 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
Sn1ÐC1 2.132 (4)
Sn1ÐC7 2.135 (3)
Sn1ÐC13 2.118 (4)
Sn1ÐO1 2.217 (3)
Sn1ÐO1w 2.311 (3)
C1ÐSn1ÐC13 118.1 (1)
C1ÐSn1ÐC7 122.7 (1)
C1ÐSn1ÐO1 97.5 (1)
C1ÐSn1ÐO1w 88.3 (1)
C7ÐSn1ÐC13 118.8 (1)
C7ÐSn1ÐO1 86.8 (1)
C7ÐSn1ÐO1w 88.4 (1)
C13ÐSn1ÐO1 92.6 (1)
C13ÐSn1ÐO1w 86.3 (1)
O1ÐSn1ÐO1w 173.9 (1)
The C-bound H atoms were positioned geometrically (CÐH = 0.95 AÊ) and were allowed to ride on their parent C atoms, with
Uiso(H) = 1.2Ueq(C). The water H atoms were located and re®ned,
subject to OÐH = 0.850.01 AÊ. A peak/hole larger than 1 e AÊÿwas
found near Sn1.
Data collection:SMART(Bruker, 1997); cell re®nement:SAINT
(Bruker, 1997); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEPII (Johnson, 1976); software used to prepare material for publication:SHELXL97.
The authors thank Dr Jan Wikaira of the University of Canterbury for the diffraction measurements, and the University of Malaya (F0142/2002B, F0717/2002A) for supporting this work.
References
Bruker (1997).SAINTandSMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Ng, S. W. (1998).Acta Cryst.C54, 1386±1389.
Ng, S. W., Kumar Das, V. G. & Kennard, C. H. L. (1996).Main Group Met. Chem.19, 113±120.
Sheldrick, G. M. (1996).SADABS. University of GoÈttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
GoÈttingen, Germany.
Figure 1
supporting information
sup-1 Acta Cryst. (2002). E58, m661–m662
supporting information
Acta Cryst. (2002). E58, m661–m662 [https://doi.org/10.1107/S1600536802019001]
Aquatriphenyl(trifluoroacetato)tin–2,4,6-tris(2-pyridyl)-1,3,5-triazine (1/1)
Chin Fei Chee, Kong Mun Lo and Seik Weng Ng
Aquatriphenyl(trifluoroacetato)tin–2,4,6-tris(2-pyridyl)-1,3,5-triazine (1/1)
Crystal data
[Sn(C2F3O2)(C6H5)3(H2O)]·C18H12N6
Mr = 793.36 Triclinic, P1 Hall symbol: -P 1
a = 10.567 (1) Å
b = 11.053 (1) Å
c = 15.438 (1) Å
α = 105.559 (2)°
β = 97.496 (2)°
γ = 101.637 (2)°
V = 1668.5 (2) Å3
Z = 2
F(000) = 800
Dx = 1.58 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 7791 reflections
θ = 2.0–26.4°
µ = 0.83 mm−1
T = 168 K
Block, light yellow 0.30 × 0.19 × 0.10 mm
Data collection
Bruker CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin = 0.789, Tmax = 0.922
21865 measured reflections 6720 independent reflections 5013 reflections with I > 2σ(I)
Rint = 0.063
θmax = 26.4°, θmin = 2.0°
h = −13→13
k = −13→7
l = −19→19
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.040
wR(F2) = 0.095
S = 0.93 6720 reflections 468 parameters 2 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0525P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 1.43 e Å−3
Δρmin = −1.49 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
supporting information
sup-3 Acta Cryst. (2002). E58, m661–m662
C37 0.0522 (4) −0.2075 (4) 0.2453 (3) 0.033 (1) C38 0.1839 (4) −0.1488 (4) 0.2529 (3) 0.031 (1) H1w1 0.526 (4) 0.144 (4) 0.366 (1) 0.06 (2)* H1w2 0.421 (3) 0.045 (3) 0.317 (3) 0.04 (1)*
H2 0.4520 0.3989 0.4404 0.035*
H3 0.3520 0.4357 0.5684 0.041*
H4 0.1320 0.3333 0.5546 0.043*
H5 0.0100 0.1942 0.4129 0.043*
H6 0.1095 0.1607 0.2856 0.036*
H8 0.6790 0.1952 0.2583 0.035*
H9 0.8873 0.3050 0.2498 0.041*
H10 0.9184 0.5018 0.2206 0.047*
H11 0.7412 0.5940 0.2027 0.053*
H12 0.5327 0.4886 0.2136 0.044*
H14 0.1106 0.0657 0.1244 0.033*
H15 0.0139 −0.1330 0.0123 0.039*
H16 0.1452 −0.2660 −0.0500 0.045*
H17 0.3724 −0.2003 −0.0016 0.055*
H18 0.4704 −0.0044 0.1124 0.043*
H25 0.6603 0.3703 0.7004 0.035*
H26 0.8644 0.4955 0.6935 0.038*
H27 0.9364 0.4531 0.5540 0.038*
H28 0.8003 0.3003 0.4256 0.038*
H30 0.4521 0.2722 0.8137 0.041*
H31 0.3959 0.2710 0.9563 0.049*
H32 0.2277 0.1001 0.9609 0.049*
H33 0.1164 −0.0561 0.8262 0.048*
H35 0.0455 −0.0976 0.4610 0.034*
H36 −0.0909 −0.2228 0.3203 0.041*
H37 −0.0002 −0.2611 0.1879 0.040*
H38 0.2206 −0.1646 0.1991 0.037*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.029 (2) 0.023 (2) 0.022 (2) 0.008 (2) 0.005 (2) 0.009 (2) C2 0.032 (2) 0.028 (2) 0.029 (2) 0.008 (2) 0.007 (2) 0.011 (2) C3 0.052 (3) 0.030 (2) 0.022 (2) 0.017 (2) 0.009 (2) 0.006 (2) C4 0.054 (3) 0.039 (3) 0.031 (2) 0.024 (2) 0.026 (2) 0.020 (2) C5 0.032 (2) 0.043 (3) 0.041 (3) 0.014 (2) 0.019 (2) 0.021 (2) C6 0.030 (2) 0.034 (2) 0.025 (2) 0.008 (2) 0.005 (2) 0.009 (2) C7 0.026 (2) 0.024 (2) 0.018 (2) 0.003 (2) 0.004 (2) 0.005 (2) C8 0.033 (2) 0.029 (2) 0.031 (2) 0.007 (2) 0.010 (2) 0.016 (2) C9 0.022 (2) 0.046 (3) 0.039 (2) 0.010 (2) 0.008 (2) 0.016 (2) C10 0.027 (2) 0.040 (3) 0.047 (3) −0.003 (2) 0.007 (2) 0.017 (2) C11 0.033 (2) 0.032 (3) 0.069 (3) −0.001 (2) 0.004 (2) 0.027 (2) C12 0.029 (2) 0.029 (2) 0.050 (3) 0.006 (2) 0.004 (2) 0.014 (2) C13 0.027 (2) 0.032 (2) 0.017 (2) 0.004 (2) 0.006 (2) 0.010 (2) C14 0.030 (2) 0.033 (2) 0.021 (2) 0.007 (2) 0.007 (2) 0.011 (2) C15 0.032 (2) 0.036 (3) 0.024 (2) 0.001 (2) 0.000 (2) 0.010 (2) C16 0.051 (3) 0.032 (3) 0.023 (2) 0.006 (2) 0.001 (2) 0.001 (2) C17 0.050 (3) 0.047 (3) 0.037 (3 0.020 (2) 0.010 (2) −0.002 (2) C18 0.033 (2) 0.046 (3) 0.026 (2) 0.010 (2) 0.008 (2) 0.004 (2) C19 0.028 (2) 0.032 (2) 0.017 (2) −0.001 (2) −0.001 (2) 0.002 (2) C20 0.036 (2) 0.048 (3) 0.040 (3) 0.014 (2) 0.002 (2) 0.019 (2) C21 0.028 (2) 0.023 (2) 0.022 (2) 0.009 (2) 0.005 (2) 0.009 (2) C22 0.034 (2) 0.027 (2) 0.025 (2) 0.015 (2) 0.010 (2) 0.013 (2) C23 0.028 (2) 0.022 (2) 0.025 (2) 0.008 (2) 0.008 (2) 0.010 (2) C24 0.024 (2) 0.026 (2) 0.028 (2) 0.011 (2) 0.004 (2) 0.015 (2) C25 0.034 (2) 0.033 (2) 0.022 (2) 0.008 (2) 0.007 (2) 0.010 (2) C26 0.028 (2) 0.030 (2) 0.033 (2) 0.003 (2) −0.002 (2) 0.009 (2) C27 0.022 (2) 0.036 (3) 0.040 (2) 0.002 (2) 0.003 (2) 0.020 (2) C28 0.026 (2) 0.045 (3) 0.027 (2) 0.009 (2) 0.007 (2) 0.018 (2) C29 0.032 (2) 0.035 (2) 0.026 (2) 0.015 (2) 0.011 (2) 0.015 (2) C30 0.040 (2) 0.040 (3) 0.026 (2) 0.013 (2) 0.011 (2) 0.014 (2) C31 0.053 (3) 0.049 (3) 0.023 (2) 0.018 (2) 0.010 (2) 0.010 (2) C32 0.048 (3) 0.063 (3) 0.026 (2) 0.023 (2) 0.018 (2) 0.025 (2) C33 0.039 (2) 0.056 (3) 0.037 (3) 0.016 (2) 0.018 (2) 0.028 (2) C34 0.029 (2) 0.022 (2) 0.025 (2) 0.006 (2) 0.005 (2) 0.011 (2) C35 0.031 (2) 0.028 (2) 0.030 (2) 0.007 (2) 0.009 (2) 0.014 (2) C36 0.028 (2) 0.033 (2) 0.041 (2) 0.000 (2) 0.002 (2) 0.017 (2) C37 0.038 (2) 0.028 (2) 0.028 (2) 0.001 (2) −0.004 (2) 0.012 (2) C38 0.043 (2) 0.030 (2) 0.022 (2) 0.008 (2) 0.006 (2) 0.013 (2)
Geometric parameters (Å, º)
Sn1—C1 2.132 (4) C23—C34 1.482 (5)
Sn1—C7 2.135 (3) C24—C25 1.382 (5)
Sn1—C13 2.118 (4) C25—C26 1.380 (5)
Sn1—O1 2.217 (3) C26—C27 1.370 (5)
Sn1—O1w 2.311 (3) C27—C28 1.380 (5)
F1—C20 1.297 (5) C29—C30 1.384 (5)
supporting information
sup-5 Acta Cryst. (2002). E58, m661–m662
F3—C20 1.312 (5) C31—C32 1.373 (6)
O1—C19 1.237 (5) C32—C33 1.375 (6)
O2—C19 1.215 (4) C34—C35 1.390 (5)
N1—C21 1.328 (4) C35—C36 1.377 (5)
N1—C23 1.334 (4) C36—C37 1.376 (5)
N2—C22 1.338 (5) C37—C38 1.387 (5)
N2—C21 1.338 (4) O1w—H1w1 0.85 (1)
N3—C22 1.329 (5) O1w—H1w2 0.85 (1)
N3—C23 1.341 (4) C2—H2 0.9500
N4—C28 1.335 (5) C3—H3 0.9500
N4—C24 1.349 (4) C4—H4 0.9500
N5—C33 1.340 (5) C5—H5 0.9500
N5—C29 1.344 (5) C6—H6 0.9500
N6—C38 1.331 (5) C8—H8 0.9500
N6—C34 1.351 (4) C9—H9 0.9500
C1—C2 1.384 (5) C10—H10 0.9500
C1—C6 1.397 (5) C11—H11 0.9500
C2—C3 1.395 (5) C12—H12 0.9500
C3—C4 1.377 (6) C14—H14 0.9500
C4—C5 1.386 (6) C15—H15 0.9500
C5—C6 1.383 (5) C16—H16 0.9500
C7—C12 1.381 (5) C17—H17 0.9500
C7—C8 1.404 (5) C18—H18 0.9500
C8—C9 1.387 (5) C25—H25 0.9500
C9—C10 1.360 (6) C26—H26 0.9500
C10—C11 1.375 (6) C27—H27 0.9500
C11—C12 1.386 (5) C28—H28 0.9500
C13—C14 1.395 (5) C30—H30 0.9500
C13—C18 1.395 (5) C31—H31 0.9500
C14—C15 1.392 (5) C32—H32 0.9500
C15—C16 1.378 (6) C33—H33 0.9500
C16—C17 1.375 (6) C35—H35 0.9500
C17—C18 1.389 (6) C36—H36 0.9500
C19—C20 1.552 (6) C37—H37 0.9500
C21—C24 1.495 (5) C38—H38 0.9500
C22—C29 1.497 (5)
C21—N1—C23 114.9 (3) Sn1—O1w—H1w1 113 (3) C22—N2—C21 114.8 (3) Sn1—O1w—H1w2 105 (3) C22—N3—C23 114.4 (3) H1w1—O1w—H1w2 106 (4)
C28—N4—C24 116.5 (3) C1—C2—H2 119.5
C33—N5—C29 116.1 (4) C3—C2—H2 119.5
C38—N6—C34 117.5 (3) C4—C3—H3 120.1
C2—C1—C6 117.9 (3) C2—C3—H3 120.1
C2—C1—Sn1 120.4 (3) C3—C4—H4 119.8
C6—C1—Sn1 121.2 (3) C5—C4—H4 119.8
C1—C2—C3 121.1 (4) C6—C5—H5 120.4
C4—C3—C2 119.8 (4) C4—C5—H5 120.4
C3—C4—C5 120.4 (4) C5—C6—H6 119.1
C6—C5—C4 119.2 (4) C1—C6—H6 119.1
C5—C6—C1 121.7 (4) C9—C8—H8 119.8
C12—C7—C8 117.6 (3) C7—C8—H8 119.8
C12—C7—Sn1 121.5 (3) C10—C9—H9 119.6
C8—C7—Sn1 120.7 (3) C8—C9—H9 119.6
C9—C8—C7 120.5 (4) C9—C10—H10 120.2
C10—C9—C8 120.8 (4) C11—C10—H10 120.2 C9—C10—C11 119.6 (4) C10—C11—H11 119.8 C10—C11—C12 120.4 (4) C12—C11—H11 119.8 C7—C12—C11 121.1 (4) C7—C12—H12 119.4 C14—C13—C18 118.2 (3) C11—C12—H12 119.4 C14—C13—Sn1 121.3 (3) C15—C14—H14 119.6 C18—C13—Sn1 120.5 (3) C13—C14—H14 119.6 C15—C14—C13 120.9 (4) C16—C15—H15 120.0 C16—C15—C14 120.0 (4) C14—C15—H15 120.0 C17—C16—C15 119.9 (4) C17—C16—H16 120.0 C16—C17—C18 120.6 (4) C15—C16—H16 120.0 C17—C18—C13 120.5 (4) C16—C17—H17 119.7 O2—C19—O1 131.3 (4) C18—C17—H17 119.7 O2—C19—C20 115.8 (4) C17—C18—H18 119.7 O1—C19—C20 112.9 (3) C13—C18—H18 119.7 F2—C20—F1 106.1 (4) C26—C25—H25 120.4 F2—C20—F3 106.4 (4) C24—C25—H25 120.4 F1—C20—F3 104.1 (5) C27—C26—H26 120.9 F2—C20—C19 112.4 (4) C25—C26—H26 120.9 F1—C20—C19 113.5 (4) C26—C27—H27 120.4 F3—C20—C19 113.6 (3) C28—C27—H27 120.4
N1—C21—N2 125.1 (3) N4—C28—H28 118.1
supporting information
sup-7 Acta Cryst. (2002). E58, m661–m662
N4—C24—C25 122.9 (3) C32—C33—H33 117.9 N4—C24—C21 115.9 (3) C36—C35—H35 120.5 C25—C24—C21 121.1 (3) C34—C35—H35 120.5 C26—C25—C24 119.3 (3) C37—C36—H36 120.3 C27—C26—C25 118.3 (4) C35—C36—H36 120.3 C26—C27—C28 119.2 (4) C36—C37—H37 120.9 N4—C28—C27 123.7 (4) C38—C37—H37 120.9 N5—C29—C30 123.6 (3) N6—C38—H38 118.1 N5—C29—C22 116.7 (3) C37—C38—H38 118.1 C30—C29—C22 119.6 (4)
O1—Sn1—C13—C14 −60.9 (3) C29—C30—C31—C32 2.2 (6) O1w—Sn1—C13—C14 125.1 (3) C30—C31—C32—C33 −1.4 (7) C1—Sn1—C13—C18 −138.4 (3) C29—N5—C33—C32 1.1 (6) C7—Sn1—C13—C18 33.8 (4) C31—C32—C33—N5 −0.3 (7) O1—Sn1—C13—C18 121.7 (3) C38—N6—C34—C35 −1.2 (5) O1w—Sn1—C13—C18 −52.3 (3) C38—N6—C34—C23 179.0 (3) C18—C13—C14—C15 0.7 (5) N1—C23—C34—N6 11.5 (5) Sn1—C13—C14—C15 −176.8 (3) N3—C23—C34—N6 −168.6 (3) C13—C14—C15—C16 −0.6 (6) N1—C23—C34—C35 −168.3 (3) C14—C15—C16—C17 −0.3 (6) N3—C23—C34—C35 11.6 (5) C15—C16—C17—C18 1.0 (7) N6—C34—C35—C36 −1.3 (6) C16—C17—C18—C13 −0.9 (7) C23—C34—C35—C36 178.5 (4) C14—C13—C18—C17 0.0 (6) C34—C35—C36—C37 2.7 (6) Sn1—C13—C18—C17 177.5 (3) C35—C36—C37—C38 −1.7 (6) Sn1—O1—C19—O2 −2.9 (7) C34—N6—C38—C37 2.3 (6) Sn1—O1—C19—C20 178.4 (2) C36—C37—C38—N6 −0.9 (6) O2—C19—C20—F2 −85.9 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A