Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028048/ww2083sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028048/ww2083Isup2.hkl |
CCDC reference: 654751
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.054
- wR factor = 0.170
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C20 - C21 .. 9.97 su PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.47 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C28 .. 5.34 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.82 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O1 .. 5.96 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C7 -C12 1.37 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C29 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C30
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
A mixture of Na2L (0.388 g, 1 mmol) and Ph3SnCl (0.770 g, 2 mmol) in 25 ml e thanol was refluxed for 12 h and then filtered. The resulting precipitates were washed with ethanol. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethyl formamide solution.
All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms. The minimum electron-density peak is located 0.96Å from atom Sn1.
To further widen the scope of application of organotin compounds, there is a need to prepare new series of organotin compounds. In this paper, the structure of (I) is described.
The title compound (I) contains one neutral [Sn2(C6H5)6(C9H5NCOO)2] molecule and two N,N-dimethyl formamide solvent molecules. As shown in Fig.1, two triphenyltin groups are bridged by the 2,2'-biquinoline-4,4'-dicarboxylate dianion, L, through its two carboxylate groups. The central Sn atom adopts distorted SnC3O2 trigonal bipyramid geometry composed of three phenyl groups, one carboxylate O atom from L and one O atom of N,N-dimethyl formamide. The N,N-dimethyl formamide, included as solvent molecule, forms no hydrogen-bonding interactions with any other atoms in the structure. In addition, the bond between Sn1 and O3 (2.605 (3) Å) is much more weaker than that of Sn1 and O1 (2.187 (4) Å) (Basu Baul et al., 2004). The L ligand of each molecule provides two quinoline rings to form slipped π-π interaction with the face-to-face distance (d) being about 3.406Å (Fig. 2).
For related literature, see: Basu Baul et al. (2004).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
Fig. 1. View of the compound (I). Displacement ellipsoids are drawn at the 30% probability level. (symmetry code: (i) 1 - x, 1 - y, 1 - z) | |
Fig. 2. A packing diagram of (I). |
[Sn2(C6H5)6(C10H5NO2)2(C3H7NO)2] | F(000) = 2408 |
Mr = 1188.47 | Dx = 1.472 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6203 reflections |
a = 30.4592 (17) Å | θ = 1.6–28.3° |
b = 9.5344 (5) Å | µ = 0.99 mm−1 |
c = 22.0343 (14) Å | T = 293 K |
β = 123.051 (2)° | Block, colourless |
V = 5363.5 (5) Å3 | 0.54 × 0.48 × 0.39 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 6203 independent reflections |
Radiation source: fine-focus sealed tube | 4618 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −40→26 |
Tmin = 0.590, Tmax = 0.678 | k = −12→10 |
15947 measured reflections | l = −26→29 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1137P)2] where P = (Fo2 + 2Fc2)/3 |
6203 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 2.82 e Å−3 |
0 restraints | Δρmin = −1.14 e Å−3 |
[Sn2(C6H5)6(C10H5NO2)2(C3H7NO)2] | V = 5363.5 (5) Å3 |
Mr = 1188.47 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 30.4592 (17) Å | µ = 0.99 mm−1 |
b = 9.5344 (5) Å | T = 293 K |
c = 22.0343 (14) Å | 0.54 × 0.48 × 0.39 mm |
β = 123.051 (2)° |
Bruker APEX CCD area-detector diffractometer | 6203 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4618 reflections with I > 2σ(I) |
Tmin = 0.590, Tmax = 0.678 | Rint = 0.033 |
15947 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.08 | Δρmax = 2.82 e Å−3 |
6203 reflections | Δρmin = −1.14 e Å−3 |
334 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.347644 (10) | 0.11246 (3) | 0.186776 (13) | 0.04892 (14) | |
C1 | 0.37845 (18) | −0.0948 (5) | 0.2087 (2) | 0.0555 (11) | |
C2 | 0.36527 (18) | −0.1935 (5) | 0.2426 (2) | 0.0593 (11) | |
H2 | 0.3448 | −0.1670 | 0.2602 | 0.071* | |
C3 | 0.3825 (2) | −0.3329 (6) | 0.2507 (3) | 0.0728 (13) | |
H3 | 0.3731 | −0.3993 | 0.2724 | 0.087* | |
C4 | 0.4137 (3) | −0.3694 (5) | 0.2257 (3) | 0.0765 (16) | |
H4 | 0.4251 | −0.4616 | 0.2304 | 0.092* | |
C5 | 0.4280 (2) | −0.2738 (7) | 0.1948 (3) | 0.0810 (15) | |
H5 | 0.4495 | −0.2999 | 0.1788 | 0.097* | |
C6 | 0.4110 (2) | −0.1384 (6) | 0.1867 (3) | 0.0693 (13) | |
H6 | 0.4216 | −0.0735 | 0.1657 | 0.083* | |
C7 | 0.27208 (17) | 0.1477 (6) | 0.1675 (2) | 0.0567 (11) | |
C8 | 0.2439 (2) | 0.0377 (8) | 0.1703 (3) | 0.0898 (17) | |
H8 | 0.2588 | −0.0513 | 0.1823 | 0.108* | |
C9 | 0.1931 (2) | 0.0564 (9) | 0.1553 (4) | 0.0997 (19) | |
H9 | 0.1751 | −0.0185 | 0.1588 | 0.120* | |
C10 | 0.1708 (2) | 0.1853 (9) | 0.1356 (3) | 0.094 (2) | |
H10 | 0.1365 | 0.1988 | 0.1225 | 0.113* | |
C11 | 0.1984 (3) | 0.2913 (9) | 0.1352 (5) | 0.121 (3) | |
H11 | 0.1839 | 0.3807 | 0.1245 | 0.145* | |
C12 | 0.2486 (3) | 0.2729 (8) | 0.1503 (4) | 0.102 (2) | |
H12 | 0.2664 | 0.3502 | 0.1485 | 0.122* | |
C13 | 0.37577 (16) | 0.2455 (4) | 0.1378 (2) | 0.0487 (9) | |
C14 | 0.3425 (2) | 0.3145 (5) | 0.0722 (3) | 0.0650 (12) | |
H14 | 0.3066 | 0.2999 | 0.0481 | 0.078* | |
C15 | 0.3608 (3) | 0.4014 (6) | 0.0428 (4) | 0.0840 (18) | |
H15 | 0.3374 | 0.4478 | −0.0002 | 0.101* | |
C16 | 0.4128 (4) | 0.4219 (6) | 0.0753 (5) | 0.096 (2) | |
H16 | 0.4253 | 0.4799 | 0.0540 | 0.116* | |
C17 | 0.4480 (3) | 0.3552 (6) | 0.1413 (4) | 0.0890 (19) | |
H17 | 0.4839 | 0.3697 | 0.1645 | 0.107* | |
C18 | 0.42890 (18) | 0.2687 (5) | 0.1710 (3) | 0.0672 (12) | |
H18 | 0.4522 | 0.2243 | 0.2147 | 0.081* | |
C19 | 0.44734 (17) | 0.1592 (6) | 0.4717 (3) | 0.0637 (12) | |
C20 | 0.4307 (2) | 0.0166 (7) | 0.4709 (4) | 0.088 (2) | |
H20 | 0.4080 | −0.0268 | 0.4267 | 0.105* | |
C21 | 0.4477 (3) | −0.0562 (8) | 0.5337 (5) | 0.0917 (18) | |
H21 | 0.4369 | −0.1483 | 0.5315 | 0.110* | |
C22 | 0.4809 (2) | 0.0069 (7) | 0.6004 (4) | 0.0861 (16) | |
H22 | 0.4915 | −0.0423 | 0.6427 | 0.103* | |
C23 | 0.4981 (2) | 0.1400 (6) | 0.6043 (3) | 0.0698 (13) | |
H23 | 0.5211 | 0.1796 | 0.6495 | 0.084* | |
C24 | 0.48187 (17) | 0.2212 (5) | 0.5406 (3) | 0.0612 (11) | |
C25 | 0.48861 (15) | 0.4313 (5) | 0.4933 (2) | 0.0549 (10) | |
C26 | 0.45349 (18) | 0.3773 (5) | 0.4212 (2) | 0.0632 (13) | |
H26 | 0.4448 | 0.4320 | 0.3812 | 0.076* | |
C27 | 0.43283 (16) | 0.2450 (6) | 0.4116 (3) | 0.0658 (14) | |
C28 | 0.3947 (2) | 0.1862 (8) | 0.3373 (3) | 0.087 (2) | |
C29 | 0.2256 (3) | −0.1292 (7) | −0.0722 (4) | 0.109 (3) | |
H29A | 0.2124 | −0.1853 | −0.1149 | 0.163* | |
H29C | 0.2084 | −0.0397 | −0.0852 | 0.163* | |
H29B | 0.2190 | −0.1759 | −0.0393 | 0.163* | |
C30 | 0.3076 (4) | −0.1706 (11) | −0.0725 (6) | 0.151 (4) | |
H30B | 0.2818 | −0.2201 | −0.1154 | 0.226* | |
H30C | 0.3346 | −0.2345 | −0.0397 | 0.226* | |
H30A | 0.3226 | −0.0972 | −0.0853 | 0.226* | |
C31 | 0.3084 (2) | −0.0349 (5) | 0.0229 (3) | 0.0668 (12) | |
H31 | 0.3437 | −0.0186 | 0.0418 | 0.080* | |
N1 | 0.50173 (14) | 0.3517 (4) | 0.55044 (19) | 0.0541 (8) | |
N2 | 0.2823 (2) | −0.1090 (4) | −0.0371 (3) | 0.0769 (13) | |
O1 | 0.40005 (16) | 0.2196 (6) | 0.2896 (2) | 0.1038 (15) | |
O2 | 0.3613 (2) | 0.0932 (5) | 0.3264 (2) | 0.0980 (14) | |
O3 | 0.29056 (13) | 0.0138 (3) | 0.05551 (17) | 0.0662 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03819 (19) | 0.0677 (2) | 0.03760 (19) | 0.00386 (11) | 0.01859 (14) | 0.00340 (11) |
C1 | 0.044 (2) | 0.078 (3) | 0.042 (2) | 0.0083 (19) | 0.0216 (19) | 0.0107 (19) |
C2 | 0.056 (3) | 0.066 (3) | 0.053 (2) | 0.006 (2) | 0.029 (2) | 0.001 (2) |
C3 | 0.062 (3) | 0.082 (3) | 0.058 (3) | −0.006 (3) | 0.023 (2) | −0.002 (3) |
C4 | 0.075 (4) | 0.064 (3) | 0.075 (4) | 0.010 (2) | 0.030 (3) | −0.005 (2) |
C5 | 0.071 (3) | 0.099 (4) | 0.084 (4) | 0.021 (3) | 0.049 (3) | 0.001 (3) |
C6 | 0.062 (3) | 0.089 (4) | 0.063 (3) | 0.016 (2) | 0.038 (3) | 0.010 (2) |
C7 | 0.042 (2) | 0.087 (3) | 0.043 (2) | 0.004 (2) | 0.0235 (18) | −0.002 (2) |
C8 | 0.059 (3) | 0.105 (4) | 0.110 (5) | 0.011 (3) | 0.049 (3) | 0.014 (4) |
C9 | 0.064 (4) | 0.131 (5) | 0.112 (5) | −0.008 (4) | 0.054 (4) | 0.004 (5) |
C10 | 0.053 (3) | 0.157 (6) | 0.078 (4) | 0.025 (4) | 0.039 (3) | 0.001 (4) |
C11 | 0.081 (4) | 0.120 (6) | 0.174 (8) | 0.037 (4) | 0.077 (5) | 0.020 (5) |
C12 | 0.070 (4) | 0.103 (5) | 0.141 (6) | 0.023 (3) | 0.063 (4) | 0.024 (4) |
C13 | 0.049 (2) | 0.052 (2) | 0.048 (2) | −0.0061 (17) | 0.0279 (18) | −0.0119 (17) |
C14 | 0.065 (3) | 0.079 (3) | 0.054 (3) | −0.006 (2) | 0.035 (2) | −0.006 (2) |
C15 | 0.122 (6) | 0.070 (3) | 0.083 (4) | 0.006 (3) | 0.070 (4) | 0.012 (3) |
C16 | 0.136 (7) | 0.064 (3) | 0.144 (7) | −0.009 (4) | 0.112 (6) | 0.003 (4) |
C17 | 0.079 (4) | 0.080 (4) | 0.133 (6) | −0.027 (3) | 0.074 (4) | −0.027 (4) |
C18 | 0.051 (3) | 0.075 (3) | 0.076 (3) | −0.006 (2) | 0.034 (2) | −0.017 (2) |
C19 | 0.037 (2) | 0.092 (3) | 0.060 (3) | 0.001 (2) | 0.025 (2) | −0.022 (3) |
C20 | 0.048 (3) | 0.097 (4) | 0.116 (5) | −0.016 (3) | 0.043 (3) | −0.049 (4) |
C21 | 0.077 (4) | 0.089 (4) | 0.126 (6) | 0.007 (3) | 0.066 (4) | 0.018 (4) |
C22 | 0.071 (4) | 0.105 (4) | 0.091 (4) | 0.007 (3) | 0.050 (3) | 0.008 (4) |
C23 | 0.065 (3) | 0.078 (3) | 0.074 (3) | 0.004 (2) | 0.042 (3) | 0.000 (3) |
C24 | 0.042 (2) | 0.084 (3) | 0.058 (3) | −0.002 (2) | 0.028 (2) | −0.015 (2) |
C25 | 0.039 (2) | 0.089 (3) | 0.0334 (18) | 0.0039 (19) | 0.0180 (17) | −0.013 (2) |
C26 | 0.042 (2) | 0.106 (4) | 0.035 (2) | 0.005 (2) | 0.0172 (19) | −0.016 (2) |
C27 | 0.034 (2) | 0.099 (4) | 0.059 (3) | −0.009 (2) | 0.022 (2) | −0.039 (3) |
C28 | 0.052 (3) | 0.156 (6) | 0.054 (3) | −0.018 (3) | 0.029 (2) | −0.045 (4) |
C29 | 0.091 (5) | 0.098 (5) | 0.091 (5) | −0.041 (4) | 0.020 (4) | −0.013 (3) |
C30 | 0.180 (9) | 0.156 (7) | 0.193 (10) | −0.066 (7) | 0.151 (9) | −0.092 (7) |
C31 | 0.059 (3) | 0.073 (3) | 0.066 (3) | −0.020 (2) | 0.032 (2) | −0.014 (2) |
N1 | 0.0448 (19) | 0.074 (2) | 0.0385 (17) | 0.0026 (17) | 0.0192 (15) | −0.0070 (16) |
N2 | 0.086 (3) | 0.078 (3) | 0.072 (3) | −0.031 (2) | 0.047 (3) | −0.023 (2) |
O1 | 0.062 (2) | 0.178 (5) | 0.048 (2) | −0.017 (3) | 0.0146 (18) | −0.008 (2) |
O2 | 0.087 (3) | 0.118 (3) | 0.071 (3) | −0.031 (2) | 0.032 (2) | −0.003 (2) |
O3 | 0.066 (2) | 0.072 (2) | 0.0561 (18) | −0.0086 (16) | 0.0304 (16) | −0.0120 (15) |
Sn1—C13 | 2.125 (4) | C17—C18 | 1.364 (8) |
Sn1—C7 | 2.127 (4) | C17—H17 | 0.9300 |
Sn1—C1 | 2.127 (4) | C18—H18 | 0.9300 |
Sn1—O1 | 2.187 (4) | C19—C27 | 1.407 (8) |
C1—C6 | 1.384 (7) | C19—C24 | 1.422 (7) |
C1—C2 | 1.390 (6) | C19—C20 | 1.447 (8) |
C2—C3 | 1.404 (7) | C20—C21 | 1.371 (9) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.377 (8) | C21—C22 | 1.387 (10) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.344 (8) | C22—C23 | 1.358 (8) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.366 (7) | C23—C24 | 1.433 (8) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—H6 | 0.9300 | C24—N1 | 1.349 (6) |
C7—C12 | 1.337 (8) | C25—N1 | 1.331 (6) |
C7—C8 | 1.378 (8) | C25—C25i | 1.436 (10) |
C8—C9 | 1.406 (8) | C25—C26 | 1.443 (6) |
C8—H8 | 0.9300 | C26—C27 | 1.373 (7) |
C9—C10 | 1.356 (11) | C26—H26 | 0.9300 |
C9—H9 | 0.9300 | C27—C28 | 1.507 (6) |
C10—C11 | 1.318 (10) | C28—O1 | 1.190 (7) |
C10—H10 | 0.9300 | C28—O2 | 1.270 (8) |
C11—C12 | 1.385 (9) | C29—N2 | 1.471 (9) |
C11—H11 | 0.9300 | C29—H29A | 0.9600 |
C12—H12 | 0.9300 | C29—H29C | 0.9600 |
C13—C18 | 1.383 (6) | C29—H29B | 0.9600 |
C13—C14 | 1.397 (7) | C30—N2 | 1.482 (9) |
C14—C15 | 1.345 (8) | C30—H30B | 0.9600 |
C14—H14 | 0.9300 | C30—H30C | 0.9600 |
C15—C16 | 1.351 (11) | C30—H30A | 0.9600 |
C15—H15 | 0.9300 | C31—O3 | 1.206 (6) |
C16—C17 | 1.403 (11) | C31—N2 | 1.316 (6) |
C16—H16 | 0.9300 | C31—H31 | 0.9300 |
C13—Sn1—C7 | 119.75 (18) | C18—C17—H17 | 120.4 |
C13—Sn1—C1 | 114.85 (16) | C16—C17—H17 | 120.4 |
C7—Sn1—C1 | 119.16 (19) | C17—C18—C13 | 121.7 (6) |
C13—Sn1—O1 | 88.78 (16) | C17—C18—H18 | 119.2 |
C7—Sn1—O1 | 103.41 (17) | C13—C18—H18 | 119.2 |
C1—Sn1—O1 | 102.48 (19) | C27—C19—C24 | 115.7 (5) |
C6—C1—C2 | 117.2 (4) | C27—C19—C20 | 127.4 (5) |
C6—C1—Sn1 | 120.7 (4) | C24—C19—C20 | 117.0 (5) |
C2—C1—Sn1 | 122.0 (3) | C21—C20—C19 | 121.8 (6) |
C1—C2—C3 | 120.7 (5) | C21—C20—H20 | 119.1 |
C1—C2—H2 | 119.7 | C19—C20—H20 | 119.1 |
C3—C2—H2 | 119.7 | C20—C21—C22 | 120.3 (6) |
C4—C3—C2 | 118.8 (5) | C20—C21—H21 | 119.9 |
C4—C3—H3 | 120.6 | C22—C21—H21 | 119.9 |
C2—C3—H3 | 120.6 | C23—C22—C21 | 120.4 (6) |
C5—C4—C3 | 121.0 (5) | C23—C22—H22 | 119.8 |
C5—C4—H4 | 119.5 | C21—C22—H22 | 119.8 |
C3—C4—H4 | 119.5 | C22—C23—C24 | 121.8 (6) |
C4—C5—C6 | 120.2 (5) | C22—C23—H23 | 119.1 |
C4—C5—H5 | 119.9 | C24—C23—H23 | 119.1 |
C6—C5—H5 | 119.9 | N1—C24—C19 | 124.1 (5) |
C5—C6—C1 | 122.1 (5) | N1—C24—C23 | 117.2 (4) |
C5—C6—H6 | 119.0 | C19—C24—C23 | 118.7 (5) |
C1—C6—H6 | 119.0 | N1—C25—C25i | 117.6 (4) |
C12—C7—C8 | 116.2 (5) | N1—C25—C26 | 119.9 (5) |
C12—C7—Sn1 | 123.5 (4) | C25i—C25—C26 | 122.5 (5) |
C8—C7—Sn1 | 120.2 (4) | C27—C26—C25 | 120.0 (5) |
C7—C8—C9 | 121.7 (6) | C27—C26—H26 | 120.0 |
C7—C8—H8 | 119.1 | C25—C26—H26 | 120.0 |
C9—C8—H8 | 119.1 | C26—C27—C19 | 120.5 (4) |
C10—C9—C8 | 119.0 (7) | C26—C27—C28 | 121.7 (6) |
C10—C9—H9 | 120.5 | C19—C27—C28 | 117.8 (5) |
C8—C9—H9 | 120.5 | O1—C28—O2 | 120.1 (5) |
C11—C10—C9 | 119.2 (6) | O1—C28—C27 | 117.7 (6) |
C11—C10—H10 | 120.4 | O2—C28—C27 | 121.8 (6) |
C9—C10—H10 | 120.4 | N2—C29—H29A | 109.5 |
C10—C11—C12 | 121.7 (7) | N2—C29—H29C | 109.5 |
C10—C11—H11 | 119.2 | H29A—C29—H29C | 109.5 |
C12—C11—H11 | 119.2 | N2—C29—H29B | 109.5 |
C7—C12—C11 | 122.1 (7) | H29A—C29—H29B | 109.5 |
C7—C12—H12 | 118.9 | H29C—C29—H29B | 109.5 |
C11—C12—H12 | 118.9 | N2—C30—H30B | 109.5 |
C18—C13—C14 | 116.8 (4) | N2—C30—H30C | 109.5 |
C18—C13—Sn1 | 120.4 (4) | H30B—C30—H30C | 109.5 |
C14—C13—Sn1 | 122.7 (3) | N2—C30—H30A | 109.5 |
C15—C14—C13 | 122.1 (5) | H30B—C30—H30A | 109.5 |
C15—C14—H14 | 119.0 | H30C—C30—H30A | 109.5 |
C13—C14—H14 | 119.0 | O3—C31—N2 | 125.7 (5) |
C14—C15—C16 | 120.5 (6) | O3—C31—H31 | 117.2 |
C14—C15—H15 | 119.7 | N2—C31—H31 | 117.2 |
C16—C15—H15 | 119.7 | C25—N1—C24 | 119.8 (4) |
C15—C16—C17 | 119.7 (5) | C31—N2—C29 | 119.4 (5) |
C15—C16—H16 | 120.2 | C31—N2—C30 | 122.6 (6) |
C17—C16—H16 | 120.2 | C29—N2—C30 | 118.0 (6) |
C18—C17—C16 | 119.1 (6) | C28—O1—Sn1 | 114.5 (4) |
C13—Sn1—C1—C6 | −4.8 (5) | C15—C16—C17—C18 | 1.0 (10) |
C7—Sn1—C1—C6 | 147.4 (4) | C16—C17—C18—C13 | −0.2 (8) |
O1—Sn1—C1—C6 | −99.3 (4) | C14—C13—C18—C17 | 0.2 (7) |
C13—Sn1—C1—C2 | 178.0 (3) | Sn1—C13—C18—C17 | −179.1 (4) |
C7—Sn1—C1—C2 | −29.8 (4) | C27—C19—C20—C21 | −179.9 (5) |
O1—Sn1—C1—C2 | 83.5 (4) | C24—C19—C20—C21 | −0.5 (7) |
C6—C1—C2—C3 | −2.9 (7) | C19—C20—C21—C22 | 1.2 (8) |
Sn1—C1—C2—C3 | 174.3 (4) | C20—C21—C22—C23 | −1.8 (9) |
C1—C2—C3—C4 | 1.4 (7) | C21—C22—C23—C24 | 1.6 (8) |
C2—C3—C4—C5 | 0.6 (8) | C27—C19—C24—N1 | −2.1 (6) |
C3—C4—C5—C6 | −0.9 (9) | C20—C19—C24—N1 | 178.5 (4) |
C4—C5—C6—C1 | −0.8 (9) | C27—C19—C24—C23 | 179.8 (4) |
C2—C1—C6—C5 | 2.7 (8) | C20—C19—C24—C23 | 0.3 (6) |
Sn1—C1—C6—C5 | −174.6 (4) | C22—C23—C24—N1 | −179.2 (5) |
C13—Sn1—C7—C12 | −26.3 (6) | C22—C23—C24—C19 | −0.9 (7) |
C1—Sn1—C7—C12 | −177.2 (5) | N1—C25—C26—C27 | 1.3 (6) |
O1—Sn1—C7—C12 | 70.0 (5) | C25i—C25—C26—C27 | −180.0 (5) |
C13—Sn1—C7—C8 | 151.7 (4) | C25—C26—C27—C19 | −2.6 (6) |
C1—Sn1—C7—C8 | 0.9 (5) | C25—C26—C27—C28 | 178.1 (4) |
O1—Sn1—C7—C8 | −111.9 (4) | C24—C19—C27—C26 | 2.9 (6) |
C12—C7—C8—C9 | 0.5 (9) | C20—C19—C27—C26 | −177.7 (4) |
Sn1—C7—C8—C9 | −177.7 (5) | C24—C19—C27—C28 | −177.8 (4) |
C7—C8—C9—C10 | 2.0 (10) | C20—C19—C27—C28 | 1.6 (7) |
C8—C9—C10—C11 | −4.1 (11) | C26—C27—C28—O1 | 33.8 (9) |
C9—C10—C11—C12 | 3.8 (13) | C19—C27—C28—O1 | −145.5 (6) |
C8—C7—C12—C11 | −0.8 (11) | C26—C27—C28—O2 | −153.2 (6) |
Sn1—C7—C12—C11 | 177.3 (7) | C19—C27—C28—O2 | 27.5 (8) |
C10—C11—C12—C7 | −1.3 (14) | C25i—C25—N1—C24 | −179.2 (4) |
C7—Sn1—C13—C18 | 151.2 (3) | C26—C25—N1—C24 | −0.4 (6) |
C1—Sn1—C13—C18 | −56.8 (4) | C19—C24—N1—C25 | 0.9 (6) |
O1—Sn1—C13—C18 | 46.4 (4) | C23—C24—N1—C25 | 179.0 (4) |
C7—Sn1—C13—C14 | −28.0 (4) | O3—C31—N2—C29 | 4.4 (8) |
C1—Sn1—C13—C14 | 124.0 (4) | O3—C31—N2—C30 | −177.3 (7) |
O1—Sn1—C13—C14 | −132.8 (4) | O2—C28—O1—Sn1 | 1.2 (9) |
C18—C13—C14—C15 | −1.0 (7) | C27—C28—O1—Sn1 | 174.3 (4) |
Sn1—C13—C14—C15 | 178.2 (4) | C13—Sn1—O1—C28 | 173.5 (5) |
C13—C14—C15—C16 | 1.9 (9) | C7—Sn1—O1—C28 | 53.1 (6) |
C14—C15—C16—C17 | −1.9 (10) | C1—Sn1—O1—C28 | −71.3 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn2(C6H5)6(C10H5NO2)2(C3H7NO)2] |
Mr | 1188.47 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 30.4592 (17), 9.5344 (5), 22.0343 (14) |
β (°) | 123.051 (2) |
V (Å3) | 5363.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.54 × 0.48 × 0.39 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.590, 0.678 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15947, 6203, 4618 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.170, 1.08 |
No. of reflections | 6203 |
No. of parameters | 334 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.82, −1.14 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.
Sn1—C13 | 2.125 (4) | Sn1—C1 | 2.127 (4) |
Sn1—C7 | 2.127 (4) | Sn1—O1 | 2.187 (4) |
C13—Sn1—C7 | 119.75 (18) | C13—Sn1—O1 | 88.78 (16) |
C13—Sn1—C1 | 114.85 (16) | C7—Sn1—O1 | 103.41 (17) |
C7—Sn1—C1 | 119.16 (19) | C1—Sn1—O1 | 102.48 (19) |
To further widen the scope of application of organotin compounds, there is a need to prepare new series of organotin compounds. In this paper, the structure of (I) is described.
The title compound (I) contains one neutral [Sn2(C6H5)6(C9H5NCOO)2] molecule and two N,N-dimethyl formamide solvent molecules. As shown in Fig.1, two triphenyltin groups are bridged by the 2,2'-biquinoline-4,4'-dicarboxylate dianion, L, through its two carboxylate groups. The central Sn atom adopts distorted SnC3O2 trigonal bipyramid geometry composed of three phenyl groups, one carboxylate O atom from L and one O atom of N,N-dimethyl formamide. The N,N-dimethyl formamide, included as solvent molecule, forms no hydrogen-bonding interactions with any other atoms in the structure. In addition, the bond between Sn1 and O3 (2.605 (3) Å) is much more weaker than that of Sn1 and O1 (2.187 (4) Å) (Basu Baul et al., 2004). The L ligand of each molecule provides two quinoline rings to form slipped π-π interaction with the face-to-face distance (d) being about 3.406Å (Fig. 2).