metal-organic papers
m666
Gaoet al. [Sn(C6H5)3(C6H4NO3)] doi:10.1107/S1600536806006726 Acta Cryst.(2006). E62, m666–m667
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
catena
-Poly[[triphenyltin(IV)]-
l
-6-oxo-1,6-dihydropyridine-3-carboxylato]
Zhong-Jun Gao, Han-Dong Yin,* Gang Li and Da-Qi Wang
College of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People’s Republic of China
Correspondence e-mail: handongyin@163.com
Key indicators
Single-crystal X-ray study T= 298 K
Mean(C–C) = 0.006 A˚ Rfactor = 0.027 wRfactor = 0.071
Data-to-parameter ratio = 14.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 20 February 2006 Accepted 23 February 2006
#2006 International Union of Crystallography All rights reserved
The title compound, [Sn(C6H5)3(C6H4NO3)], possesses an
infinite chain structure. The SnO2C3 centre has distorted
trigonal–bipyramidal geometry with the O atoms in the apical positions. A strong intermolecular N—H O hydrogen bond results in the formation of double chains.
Comment
The title compound, (I) (Fig. 1), possesses an infinite one-dimensional chain structure arising from Sn—O bridges to the 6-hydroxy-3-pyridinecarboxylate ligand, one of which is substantially longer than the other (Table 1).
The Sn atom has distorted trigonal–bipyramidal geometry, with atoms O1 and O3i[symmetry code: (i)x,y1,z] in axial positions [O1—Sn1—O3i= 175.31 (9)] and the C atoms of the three phenyl groups in equatorial positions. The sum of the equatorial C—Sn—C angles is 359.2, indicating approximate
coplanarity for these atoms. The SnO2C3 geometry in (I) is
similar to those seen previously in related compounds (Xieet al., 1991).
A strong intermolecular N—H O hydrogen bond (Table 2) between the NH group of the pyridine ring and the non-coordinated O2 atom of a nearby carboxylate group results in the formation of a double chain parallel tob(Fig. 2).
Experimental
Crystal data
[Sn(C6H5)3(C6H4NO3)]
Mr= 488.09
Monoclinic,P21=c
a= 9.5629 (17) A˚
b= 10.6579 (19) A˚
c= 21.353 (4) A˚
= 101.155 (3)
V= 2135.2 (7) A˚3
Z= 4
Dx= 1.518 Mg m
3
MoKradiation Cell parameters from 5143
reflections
= 2.2–27.8 = 1.22 mm1
T= 298 (2) K Block, colourless 0.490.460.41 mm
Data collection
Bruker SMART CCD diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 1998)
Tmin= 0.586,Tmax= 0.635
10839 measured reflections
3755 independent reflections 3053 reflections withI> 2(I)
Rint= 0.041
max= 25.0
h=9!11
k=12!12
l=24!25
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.027
wR(F2) = 0.071
S= 1.00 3755 reflections 262 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.034P)2
+ 0.6145P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.52 e A˚
3
min=0.47 e A˚
[image:2.610.48.296.70.242.2]3
Table 1
Selected geometric parameters (A˚ ,).
Sn1—C19 2.133 (3) Sn1—C13 2.134 (3) Sn1—C7 2.137 (3) Sn1—O1 2.150 (2)
Sn1—O3i
2.356 (2) C1—O1 1.292 (4) C1—O2 1.233 (4) C19—Sn1—C13 130.80 (12)
C19—Sn1—C7 115.76 (12) C13—Sn1—C7 112.63 (12) C19—Sn1—O1 92.09 (10) C13—Sn1—O1 96.30 (11)
C7—Sn1—O1 90.01 (10) C19—Sn1—O3i
83.52 (11) C13—Sn1—O3i 87.84 (11) C7—Sn1—O3i
90.42 (10) O1—Sn1—O3i
175.31 (9)
Symmetry code: (i)x;y1;z.
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N1—H1 O2ii
0.86 1.95 2.785 (4) 165
Symmetry code: (ii)xþ1;yþ1 2;zþ
1 2.
H atoms were positioned geometrically [N—H = 0.86 A˚ and C— H = 0.93 A˚ ] and refined as riding withUiso(H) = 1.2Ueq(C,N).
Data collection:SMART(Bruker, 1998); cell refinement:SAINT
(Bruker, 1998); 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, 1998); software used to prepare material for publication:SHELXTL.
We acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University, People’s Republic of China.
References
Bruker (1998).SMART,SAINT,SADABSandSHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Xie, Q. L., Xu, X. H., Wang, H. G., Yao, X. K., Wang, R. J., Zhang, Z. G. & Hu, J. M. (1991).Acta Chim. Sin.49, 1085–1093.
Figure 1
[image:2.610.311.566.186.281.2]The molecular structure of (I), with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). [Symmetry codes: (i)x,y1, z; (ii)x,y+ 1,z.]
Figure 2
[image:2.610.43.298.303.390.2]supporting information
sup-1
Acta Cryst. (2006). E62, m666–m667
supporting information
Acta Cryst. (2006). E62, m666–m667 [https://doi.org/10.1107/S1600536806006726]
catena
-Poly[[triphenyltin(IV)]-
µ
-6-oxo1,6-dihydropyridine-3-carboxylato]
Zhong-Jun Gao, Han-Dong Yin, Gang Li and Da-Qi Wang
catena-Poly[[triphenyltin(IV)]-µ-6-hydroxypyridine-3-carboxylato]
Crystal data
[Sn(C6H5)3(C6H4NO3)] Mr = 488.09
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 9.5629 (17) Å
b = 10.6579 (19) Å
c = 21.353 (4) Å
β = 101.155 (3)°
V = 2135.2 (7) Å3
Z = 4
F(000) = 976
Dx = 1.518 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 5143 reflections
θ = 2.2–27.8°
µ = 1.22 mm−1
T = 298 K
Block, colourless 0.49 × 0.46 × 0.41 mm
Data collection
Bruker SMART CCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 1998)
Tmin = 0.586, Tmax = 0.635
10839 measured reflections 3755 independent reflections 3053 reflections with I > 2σ(I)
Rint = 0.041
θmax = 25.0°, θmin = 1.9°
h = −9→11
k = −12→12
l = −24→25
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.027 wR(F2) = 0.071
S = 1.00
3755 reflections 262 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.034P)2 + 0.6145P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.52 e Å−3
Δρmin = −0.47 e Å−3
Special details
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)
x y z Uiso*/Ueq
Sn1 0.38463 (2) 0.22844 (2) 0.371584 (10) 0.03163 (9)
N1 0.4684 (3) 0.8383 (2) 0.31816 (13) 0.0412 (7)
H1 0.5020 0.8854 0.2919 0.049*
O1 0.3573 (2) 0.4286 (2) 0.37293 (10) 0.0406 (6)
O2 0.4407 (3) 0.4558 (2) 0.28338 (11) 0.0516 (7)
O3 0.4339 (3) 1.0117 (2) 0.37454 (12) 0.0543 (6)
C1 0.4027 (3) 0.4975 (3) 0.33130 (15) 0.0370 (7)
C2 0.4619 (4) 0.7144 (3) 0.30654 (15) 0.0385 (8)
H2 0.4940 0.6832 0.2712 0.046*
C3 0.4092 (3) 0.6339 (3) 0.34543 (14) 0.0311 (7)
C4 0.3660 (3) 0.6863 (3) 0.39925 (15) 0.0379 (8)
H4 0.3307 0.6338 0.4273 0.045*
C5 0.3746 (4) 0.8110 (3) 0.41112 (16) 0.0425 (8)
H5 0.3467 0.8419 0.4475 0.051*
C6 0.4251 (4) 0.8959 (3) 0.36931 (15) 0.0395 (8)
C7 0.2975 (3) 0.2123 (3) 0.45612 (15) 0.0366 (8)
C8 0.2362 (4) 0.1009 (4) 0.4700 (2) 0.0675 (13)
H8 0.2306 0.0339 0.4418 0.081*
C9 0.1831 (6) 0.0879 (5) 0.5256 (3) 0.0968 (19)
H9 0.1435 0.0119 0.5348 0.116*
C10 0.1886 (6) 0.1860 (6) 0.5668 (2) 0.0900 (17)
H10 0.1539 0.1766 0.6043 0.108*
C11 0.2440 (5) 0.2965 (5) 0.5536 (2) 0.0733 (14)
H11 0.2454 0.3640 0.5813 0.088*
C12 0.2991 (4) 0.3099 (4) 0.49839 (17) 0.0536 (10)
H12 0.3379 0.3865 0.4898 0.064*
C13 0.2302 (3) 0.1953 (3) 0.28674 (15) 0.0376 (8)
C14 0.2259 (4) 0.0894 (3) 0.24924 (17) 0.0528 (9)
H14 0.2989 0.0307 0.2586 0.063*
C15 0.1152 (5) 0.0684 (4) 0.19798 (19) 0.0695 (12)
H15 0.1147 −0.0035 0.1733 0.083*
C16 0.0067 (5) 0.1534 (6) 0.1837 (2) 0.0863 (16)
H16 −0.0682 0.1391 0.1496 0.104*
C17 0.0087 (5) 0.2593 (5) 0.2196 (2) 0.0890 (17)
H17 −0.0647 0.3175 0.2098 0.107*
C18 0.1192 (4) 0.2807 (4) 0.27052 (19) 0.0612 (11)
H18 0.1194 0.3537 0.2944 0.073*
C19 0.6108 (3) 0.2454 (3) 0.38611 (15) 0.0382 (8)
C20 0.6747 (4) 0.3350 (4) 0.42928 (17) 0.0531 (9)
supporting information
sup-3
Acta Cryst. (2006). E62, m666–m667
C21 0.8207 (5) 0.3483 (5) 0.4441 (2) 0.0785 (14)
H21 0.8627 0.4062 0.4746 0.094*
C22 0.9026 (5) 0.2745 (5) 0.4130 (3) 0.0827 (16)
H22 1.0011 0.2848 0.4217 0.099*
C23 0.8441 (5) 0.1876 (5) 0.3704 (2) 0.0763 (14)
H23 0.9021 0.1392 0.3496 0.092*
C24 0.6973 (4) 0.1696 (4) 0.35701 (18) 0.0539 (10)
H24 0.6574 0.1071 0.3287 0.065*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Sn1 0.03997 (14) 0.02032 (14) 0.03523 (13) −0.00202 (9) 0.00883 (10) −0.00077 (9)
N1 0.0582 (18) 0.0239 (16) 0.0461 (17) −0.0021 (13) 0.0214 (14) 0.0053 (13)
O1 0.0616 (15) 0.0190 (12) 0.0444 (13) −0.0018 (10) 0.0183 (12) 0.0007 (10)
O2 0.0845 (18) 0.0317 (14) 0.0465 (14) 0.0005 (12) 0.0325 (13) −0.0098 (11)
O3 0.0843 (18) 0.0149 (13) 0.0638 (16) 0.0025 (12) 0.0149 (13) −0.0018 (11)
C1 0.0432 (19) 0.0241 (18) 0.044 (2) −0.0001 (14) 0.0088 (15) −0.0005 (15)
C2 0.055 (2) 0.026 (2) 0.0373 (18) 0.0025 (15) 0.0169 (16) −0.0022 (14)
C3 0.0409 (17) 0.0211 (17) 0.0313 (16) 0.0016 (13) 0.0074 (14) −0.0001 (13)
C4 0.053 (2) 0.0275 (18) 0.0359 (17) −0.0011 (15) 0.0164 (15) 0.0021 (14)
C5 0.063 (2) 0.0272 (19) 0.0408 (19) 0.0038 (17) 0.0177 (17) −0.0025 (15)
C6 0.051 (2) 0.025 (2) 0.0397 (19) 0.0037 (15) 0.0016 (16) 0.0001 (14)
C7 0.0373 (18) 0.036 (2) 0.0374 (17) 0.0049 (14) 0.0093 (14) 0.0082 (14)
C8 0.088 (3) 0.037 (2) 0.091 (3) 0.012 (2) 0.050 (3) 0.019 (2)
C9 0.126 (4) 0.064 (3) 0.123 (5) 0.024 (3) 0.081 (4) 0.050 (3)
C10 0.101 (4) 0.118 (5) 0.064 (3) 0.035 (4) 0.049 (3) 0.039 (3)
C11 0.069 (3) 0.109 (4) 0.046 (2) 0.004 (3) 0.019 (2) −0.015 (3)
C12 0.055 (2) 0.061 (3) 0.046 (2) −0.007 (2) 0.0134 (18) −0.0083 (19)
C13 0.0410 (18) 0.036 (2) 0.0371 (18) −0.0057 (15) 0.0094 (14) −0.0007 (15)
C14 0.066 (2) 0.043 (2) 0.046 (2) −0.0071 (19) 0.0045 (19) −0.0033 (17)
C15 0.080 (3) 0.072 (3) 0.053 (3) −0.025 (3) 0.004 (2) −0.018 (2)
C16 0.059 (3) 0.138 (5) 0.056 (3) −0.015 (3) −0.005 (2) −0.013 (3)
C17 0.057 (3) 0.127 (5) 0.075 (3) 0.028 (3) −0.008 (2) −0.007 (3)
C18 0.056 (2) 0.069 (3) 0.055 (2) 0.015 (2) 0.0026 (19) −0.011 (2)
C19 0.0349 (18) 0.039 (2) 0.0415 (19) −0.0014 (15) 0.0082 (15) 0.0077 (15)
C20 0.048 (2) 0.057 (3) 0.052 (2) −0.0094 (19) 0.0042 (18) −0.0028 (19)
C21 0.066 (3) 0.086 (4) 0.073 (3) −0.021 (3) −0.012 (2) 0.010 (3)
C22 0.048 (3) 0.087 (4) 0.113 (4) −0.006 (3) 0.018 (3) 0.040 (3)
C23 0.057 (3) 0.082 (4) 0.096 (4) 0.019 (3) 0.029 (3) 0.032 (3)
C24 0.055 (2) 0.044 (2) 0.064 (2) 0.0082 (19) 0.0164 (19) 0.0053 (19)
Geometric parameters (Å, º)
Sn1—C19 2.133 (3) C10—H10 0.9300
Sn1—C13 2.134 (3) C11—C12 1.388 (5)
Sn1—C7 2.137 (3) C11—H11 0.9300
Sn1—O3i 2.356 (2) C13—C14 1.380 (5)
N1—C2 1.343 (4) C13—C18 1.391 (5)
N1—C6 1.385 (4) C14—C15 1.385 (5)
N1—H1 0.8600 C14—H14 0.9300
C1—O1 1.292 (4) C15—C16 1.367 (6)
C1—O2 1.233 (4) C15—H15 0.9300
O3—C6 1.240 (4) C16—C17 1.363 (7)
O3—Sn1ii 2.356 (2) C16—H16 0.9300
C1—C3 1.483 (4) C17—C18 1.380 (6)
C2—C3 1.357 (4) C17—H17 0.9300
C2—H2 0.9300 C18—H18 0.9300
C3—C4 1.410 (4) C19—C20 1.384 (5)
C4—C5 1.353 (5) C19—C24 1.386 (4)
C4—H4 0.9300 C20—C21 1.378 (5)
C5—C6 1.420 (5) C20—H20 0.9300
C5—H5 0.9300 C21—C22 1.369 (7)
C7—C12 1.375 (5) C21—H21 0.9300
C7—C8 1.382 (5) C22—C23 1.343 (7)
C8—C9 1.385 (6) C22—H22 0.9300
C8—H8 0.9300 C23—C24 1.391 (5)
C9—C10 1.361 (7) C23—H23 0.9300
C9—H9 0.9300 C24—H24 0.9300
C10—C11 1.344 (7)
C19—Sn1—C13 130.80 (12) C9—C10—H10 119.8
C19—Sn1—C7 115.76 (12) C10—C11—C12 119.9 (5)
C13—Sn1—C7 112.63 (12) C10—C11—H11 120.1
C19—Sn1—O1 92.09 (10) C12—C11—H11 120.1
C13—Sn1—O1 96.30 (11) C7—C12—C11 121.5 (4)
C7—Sn1—O1 90.01 (10) C7—C12—H12 119.3
C19—Sn1—O3i 83.52 (11) C11—C12—H12 119.3
C13—Sn1—O3i 87.84 (11) C14—C13—C18 117.1 (3)
C7—Sn1—O3i 90.42 (10) C14—C13—Sn1 124.5 (3)
O1—Sn1—O3i 175.31 (9) C18—C13—Sn1 118.2 (3)
C2—N1—C6 124.9 (3) C13—C14—C15 121.5 (4)
C2—N1—H1 117.6 C13—C14—H14 119.2
C6—N1—H1 117.6 C15—C14—H14 119.2
C1—O1—Sn1 119.82 (19) C16—C15—C14 120.0 (4)
C6—O3—Sn1ii 164.4 (3) C16—C15—H15 120.0
O2—C1—O1 123.9 (3) C14—C15—H15 120.0
O2—C1—C3 121.0 (3) C17—C16—C15 119.7 (4)
O1—C1—C3 115.1 (3) C17—C16—H16 120.1
N1—C2—C3 121.2 (3) C15—C16—H16 120.1
N1—C2—H2 119.4 C16—C17—C18 120.4 (5)
C3—C2—H2 119.4 C16—C17—H17 119.8
C2—C3—C4 116.7 (3) C18—C17—H17 119.8
C2—C3—C1 120.1 (3) C17—C18—C13 121.3 (4)
supporting information
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Acta Cryst. (2006). E62, m666–m667
C5—C4—C3 121.7 (3) C13—C18—H18 119.4
C5—C4—H4 119.1 C20—C19—C24 118.4 (3)
C3—C4—H4 119.1 C20—C19—Sn1 117.4 (2)
C4—C5—C6 121.6 (3) C24—C19—Sn1 124.2 (3)
C4—C5—H5 119.2 C21—C20—C19 121.4 (4)
C6—C5—H5 119.2 C21—C20—H20 119.3
O3—C6—N1 119.1 (3) C19—C20—H20 119.3
O3—C6—C5 127.1 (3) C22—C21—C20 118.6 (5)
N1—C6—C5 113.8 (3) C22—C21—H21 120.7
C12—C7—C8 117.4 (3) C20—C21—H21 120.7
C12—C7—Sn1 122.5 (3) C23—C22—C21 121.5 (5)
C8—C7—Sn1 120.1 (3) C23—C22—H22 119.2
C7—C8—C9 120.8 (4) C21—C22—H22 119.2
C7—C8—H8 119.6 C22—C23—C24 120.4 (5)
C9—C8—H8 119.6 C22—C23—H23 119.8
C10—C9—C8 120.1 (5) C24—C23—H23 119.8
C10—C9—H9 119.9 C19—C24—C23 119.6 (4)
C8—C9—H9 119.9 C19—C24—H24 120.2
C11—C10—C9 120.3 (4) C23—C24—H24 120.2
C11—C10—H10 119.8
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N1—H1···O2iii 0.86 1.95 2.785 (4) 165
