Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027237/hk2268sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027237/hk2268Isup2.hkl |
CCDC reference: 654740
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.020 Å
- Disorder in main residue
- R factor = 0.058
- wR factor = 0.163
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -C 2yc PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 20 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 3260 Count of symmetry unique reflns 1826 Completeness (_total/calc) 178.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1434 Fraction of Friedel pairs measured 0.785 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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
For the preparation of the title compound, a mixture of tri-n-butyltin oxide (596.1 mg, 2 mmol) and pyridine-3-carboxylic acid (246.2 mg, 2 mmol), in methanol (80 ml) was heated under reflux for 12 h. The resulting clear solution was evaporated under vacuum. The product was crystallized from ethanol (yield; 446.3 mg, 82%, m.p. 398 K).
When the crystal structure was solved, the atoms C9, C10, C12, C13 and C14 were found to be disordered. During the refinement proccess, the occupancies of C9, C12 and C14 were kept fixed as C9 = 1/4, C9' = 3/4, C12 = 1/2, C12' = 1/2, C14 = 0.50 and C14' = 1/2, while the remainings were refined as C10 = 0.39 (3), C10' = 0.61 (3), C13 = 0.39 (3) and C13' = 0.61 (3). H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities as well as their industrial and agricultural applications (Gielen et al., 1988). pyridine-3-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures.
The asymmetric unit of the title compound, (I), (Fig. 1), consists of three butyl and one (pyridine-3-carboxylate) groups bonded to the tin atom, where the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
The tin atom has a distorted trigonal bipyramidal geometry with atoms O1 and N1i of the pyridine-3-carboxylic acid [symmetry code: (i) x, y, z - 1], in axial and C atoms of the three butyl groups in equatorial positions, as in the similar compound (Ma et al., 2004).
In the crystal structure, (Fig. 2), the molecules are linked to form an infinite one-dimensional polymeric chain structure.
For general backgroud, see: Allen et al. (1987); Gielen et al. (1988). For related literature, see: Ma et al. (2004).
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: SHELXL97.
[Sn(C4H9)3(C6H4NO2)] | F(000) = 848 |
Mr = 412.13 | Dx = 1.333 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3313 reflections |
a = 9.594 (4) Å | θ = 2.3–28.1° |
b = 24.286 (11) Å | µ = 1.25 mm−1 |
c = 9.715 (4) Å | T = 298 K |
β = 114.864 (5)° | Block, colorless |
V = 2053.7 (15) Å3 | 0.53 × 0.46 × 0.41 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3260 independent reflections |
Radiation source: fine-focus sealed tube | 2741 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→9 |
Tmin = 0.529, Tmax = 0.597 | k = −28→22 |
5123 measured reflections | l = −11→11 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.1189P)2 + 1.6655P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.163 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 1.41 e Å−3 |
3260 reflections | Δρmin = −0.73 e Å−3 |
219 parameters | Absolute structure: Flack (1983), 1798 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (10) |
Secondary atom site location: difference Fourier map |
[Sn(C4H9)3(C6H4NO2)] | V = 2053.7 (15) Å3 |
Mr = 412.13 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 9.594 (4) Å | µ = 1.25 mm−1 |
b = 24.286 (11) Å | T = 298 K |
c = 9.715 (4) Å | 0.53 × 0.46 × 0.41 mm |
β = 114.864 (5)° |
Bruker SMART CCD area-detector diffractometer | 3260 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2741 reflections with I > 2σ(I) |
Tmin = 0.529, Tmax = 0.597 | Rint = 0.037 |
5123 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.163 | Δρmax = 1.41 e Å−3 |
S = 1.00 | Δρmin = −0.73 e Å−3 |
3260 reflections | Absolute structure: Flack (1983), 1798 Friedel pairs |
219 parameters | Absolute structure parameter: 0.06 (10) |
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 | Occ. (<1) | |
Sn1 | 0.5451 (3) | 0.87521 (2) | 0.0427 (3) | 0.0500 (2) | |
O1 | 0.5354 (16) | 0.8687 (4) | 0.2610 (13) | 0.062 (3) | |
O2 | 0.6522 (12) | 0.9490 (3) | 0.3408 (10) | 0.076 (2) | |
N1 | 0.552 (2) | 0.8833 (5) | 0.779 (2) | 0.064 (4) | |
C1 | 0.6275 (15) | 0.9254 (5) | 0.7557 (12) | 0.065 (2) | |
H1 | 0.6718 | 0.9504 | 0.8346 | 0.078* | |
C2 | 0.6459 (14) | 0.9350 (5) | 0.6238 (12) | 0.062 (2) | |
H2 | 0.7027 | 0.9648 | 0.6157 | 0.074* | |
C3 | 0.5757 (14) | 0.8981 (5) | 0.5027 (12) | 0.0552 (18) | |
C4 | 0.4984 (13) | 0.8535 (5) | 0.5264 (13) | 0.061 (2) | |
H4 | 0.4544 | 0.8273 | 0.4504 | 0.073* | |
C5 | 0.4862 (16) | 0.8476 (5) | 0.6631 (13) | 0.0630 (19) | |
H5 | 0.4310 | 0.8180 | 0.6754 | 0.076* | |
C6 | 0.5913 (15) | 0.9068 (5) | 0.3591 (14) | 0.0663 (19) | |
C7 | 0.4511 (18) | 0.7949 (5) | −0.0192 (16) | 0.083 (2) | |
H7A | 0.3408 | 0.7973 | −0.0520 | 0.100* | |
H7B | 0.4688 | 0.7830 | −0.1058 | 0.100* | |
C8 | 0.5117 (19) | 0.7515 (5) | 0.1005 (18) | 0.095 (3) | |
H8A | 0.5009 | 0.7646 | 0.1899 | 0.114* | |
H8B | 0.6206 | 0.7471 | 0.1279 | 0.114* | |
C9 | 0.4371 (19) | 0.6958 (5) | 0.0598 (17) | 0.098 (3) | 0.25 |
H9A | 0.4865 | 0.6747 | 0.0081 | 0.118* | 0.25 |
H9B | 0.3298 | 0.7003 | −0.0094 | 0.118* | 0.25 |
C10 | 0.448 (6) | 0.6638 (16) | 0.200 (4) | 0.109 (7) | 0.39 (3) |
H10A | 0.3992 | 0.6286 | 0.1697 | 0.163* | 0.39 (3) |
H10B | 0.3973 | 0.6842 | 0.2508 | 0.163* | 0.39 (3) |
H10C | 0.5539 | 0.6587 | 0.2683 | 0.163* | 0.39 (3) |
C9' | 0.4371 (19) | 0.6958 (5) | 0.0598 (17) | 0.098 (3) | 0.75 |
H9'1 | 0.4335 | 0.6853 | −0.0380 | 0.118* | 0.75 |
H9'2 | 0.3318 | 0.6993 | 0.0476 | 0.118* | 0.75 |
C10' | 0.512 (4) | 0.6492 (11) | 0.170 (3) | 0.097 (6) | 0.61 (3) |
H10D | 0.4552 | 0.6158 | 0.1314 | 0.145* | 0.61 (3) |
H10E | 0.5113 | 0.6578 | 0.2665 | 0.145* | 0.61 (3) |
H10F | 0.6156 | 0.6445 | 0.1825 | 0.145* | 0.61 (3) |
C11 | 0.3914 (15) | 0.9411 (6) | −0.0442 (16) | 0.081 (2) | |
H11A | 0.4521 | 0.9740 | −0.0354 | 0.097* | |
H11B | 0.3323 | 0.9344 | −0.1517 | 0.097* | |
C12 | 0.2810 (15) | 0.9542 (7) | 0.0208 (16) | 0.089 (2) | 0.50 |
H12A | 0.3310 | 0.9779 | 0.1084 | 0.107* | 0.50 |
H12B | 0.2525 | 0.9204 | 0.0554 | 0.107* | 0.50 |
C13 | 0.133 (3) | 0.983 (2) | −0.093 (3) | 0.091 (4) | 0.39 (3) |
H13A | 0.1627 | 1.0105 | −0.1486 | 0.109* | 0.39 (3) |
H13B | 0.0701 | 0.9560 | −0.1654 | 0.109* | 0.39 (3) |
C14 | 0.0394 (19) | 1.0105 (8) | −0.025 (2) | 0.132 (4) | 0.50 |
H14A | −0.0556 | 1.0228 | −0.1043 | 0.198* | 0.50 |
H14B | 0.0944 | 1.0415 | 0.0340 | 0.198* | 0.50 |
H14C | 0.0182 | 0.9849 | 0.0391 | 0.198* | 0.50 |
C12' | 0.2810 (15) | 0.9542 (7) | 0.0208 (16) | 0.089 (2) | 0.50 |
H12C | 0.3371 | 0.9558 | 0.1303 | 0.107* | 0.50 |
H12D | 0.2086 | 0.9240 | −0.0024 | 0.107* | 0.50 |
C13' | 0.188 (3) | 1.0082 (10) | −0.032 (4) | 0.092 (3) | 0.61 (3) |
H13C | 0.2511 | 1.0382 | 0.0284 | 0.110* | 0.61 (3) |
H13D | 0.1719 | 1.0150 | −0.1366 | 0.110* | 0.61 (3) |
C14' | 0.0394 (19) | 1.0105 (8) | −0.025 (2) | 0.132 (4) | 0.50 |
H14D | −0.0082 | 1.0454 | −0.0624 | 0.198* | 0.50 |
H14E | 0.0537 | 1.0059 | 0.0782 | 0.198* | 0.50 |
H14F | −0.0253 | 0.9815 | −0.0862 | 0.198* | 0.50 |
C15 | 0.7867 (15) | 0.8816 (5) | 0.1302 (18) | 0.079 (2) | |
H15A | 0.8117 | 0.9151 | 0.0910 | 0.095* | |
H15B | 0.8272 | 0.8854 | 0.2395 | 0.095* | |
C16 | 0.8680 (14) | 0.8340 (6) | 0.0944 (18) | 0.094 (3) | |
H16A | 0.8338 | 0.8310 | −0.0145 | 0.112* | |
H16B | 0.8429 | 0.7999 | 0.1309 | 0.112* | |
C17 | 1.0445 (14) | 0.8435 (7) | 0.1717 (19) | 0.100 (3) | |
H17A | 1.0681 | 0.8768 | 0.1306 | 0.121* | |
H17B | 1.0756 | 0.8493 | 0.2794 | 0.121* | |
C18 | 1.1349 (18) | 0.7980 (8) | 0.152 (3) | 0.128 (6) | |
H18A | 1.2424 | 0.8056 | 0.2075 | 0.192* | |
H18B | 1.1118 | 0.7941 | 0.0459 | 0.192* | |
H18C | 1.1095 | 0.7645 | 0.1884 | 0.192* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0625 (4) | 0.0587 (3) | 0.0297 (3) | 0.0009 (5) | 0.0204 (2) | 0.0023 (4) |
O1 | 0.068 (6) | 0.075 (6) | 0.046 (7) | −0.003 (4) | 0.027 (5) | −0.001 (4) |
O2 | 0.117 (7) | 0.073 (5) | 0.060 (5) | −0.028 (5) | 0.058 (5) | −0.003 (4) |
N1 | 0.086 (9) | 0.067 (7) | 0.052 (9) | −0.011 (6) | 0.041 (8) | −0.019 (6) |
C1 | 0.088 (4) | 0.071 (4) | 0.043 (4) | −0.006 (4) | 0.035 (3) | −0.004 (3) |
C2 | 0.084 (4) | 0.066 (4) | 0.042 (4) | −0.007 (4) | 0.032 (3) | −0.002 (3) |
C3 | 0.077 (4) | 0.058 (4) | 0.039 (4) | 0.000 (3) | 0.034 (3) | −0.005 (3) |
C4 | 0.083 (4) | 0.073 (4) | 0.040 (4) | −0.012 (3) | 0.039 (4) | −0.007 (4) |
C5 | 0.086 (4) | 0.075 (4) | 0.042 (4) | −0.013 (4) | 0.040 (3) | −0.002 (3) |
C6 | 0.082 (4) | 0.077 (4) | 0.050 (3) | 0.002 (3) | 0.038 (3) | 0.007 (3) |
C7 | 0.096 (5) | 0.087 (5) | 0.070 (4) | −0.007 (4) | 0.038 (4) | 0.009 (4) |
C8 | 0.103 (6) | 0.085 (5) | 0.086 (6) | −0.006 (5) | 0.029 (5) | 0.016 (5) |
C9 | 0.110 (5) | 0.090 (5) | 0.085 (5) | −0.005 (4) | 0.032 (4) | 0.012 (4) |
C10 | 0.115 (11) | 0.099 (10) | 0.099 (11) | −0.004 (10) | 0.032 (10) | 0.018 (10) |
C9' | 0.110 (5) | 0.090 (5) | 0.085 (5) | −0.005 (4) | 0.032 (4) | 0.012 (4) |
C10' | 0.110 (10) | 0.101 (10) | 0.086 (9) | −0.004 (9) | 0.048 (8) | 0.013 (9) |
C11 | 0.090 (4) | 0.092 (4) | 0.068 (4) | 0.016 (4) | 0.041 (4) | 0.014 (4) |
C12 | 0.097 (4) | 0.100 (4) | 0.076 (4) | 0.019 (4) | 0.042 (4) | 0.009 (4) |
C13 | 0.099 (6) | 0.104 (6) | 0.077 (6) | 0.018 (6) | 0.043 (5) | 0.010 (5) |
C14 | 0.131 (7) | 0.132 (7) | 0.107 (7) | 0.018 (6) | 0.025 (6) | 0.012 (6) |
C12' | 0.097 (4) | 0.100 (4) | 0.076 (4) | 0.019 (4) | 0.042 (4) | 0.009 (4) |
C13' | 0.098 (6) | 0.104 (6) | 0.080 (6) | 0.018 (5) | 0.043 (5) | 0.011 (5) |
C14' | 0.131 (7) | 0.132 (7) | 0.107 (7) | 0.018 (6) | 0.025 (6) | 0.012 (6) |
C15 | 0.078 (4) | 0.097 (5) | 0.069 (5) | 0.001 (4) | 0.037 (4) | 0.007 (4) |
C16 | 0.087 (5) | 0.109 (6) | 0.086 (6) | 0.002 (5) | 0.038 (5) | 0.005 (5) |
C17 | 0.089 (6) | 0.121 (7) | 0.092 (7) | −0.002 (6) | 0.039 (6) | 0.001 (6) |
C18 | 0.097 (9) | 0.156 (12) | 0.119 (11) | −0.003 (9) | 0.033 (9) | −0.021 (10) |
Sn1—C11 | 2.099 (12) | C10—H10C | 0.9600 |
Sn1—C15 | 2.112 (13) | C10'—H10D | 0.9600 |
Sn1—C7 | 2.127 (13) | C10'—H10E | 0.9600 |
Sn1—O1 | 2.167 (12) | C10'—H10F | 0.9600 |
Sn1—N1i | 2.603 (16) | C11—C12 | 1.477 (13) |
Sn1—O2 | 3.186 (9) | C11—H11A | 0.9700 |
O1—C6 | 1.274 (13) | C11—H11B | 0.9700 |
O2—C6 | 1.230 (12) | C12—C13 | 1.550 (17) |
N1—C1 | 1.322 (19) | C12—H12A | 0.9700 |
N1—C5 | 1.347 (18) | C12—H12B | 0.9700 |
C1—C2 | 1.385 (15) | C13—C14 | 1.480 (18) |
C1—H1 | 0.9300 | C13—H13A | 0.9700 |
C2—C3 | 1.405 (15) | C13—H13B | 0.9700 |
C2—H2 | 0.9300 | C13'—H13C | 0.9700 |
C3—C4 | 1.386 (16) | C13'—H13D | 0.9700 |
C3—C6 | 1.479 (15) | C14—H14A | 0.9600 |
C4—C5 | 1.388 (15) | C14—H14B | 0.9600 |
C4—H4 | 0.9300 | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | C15—C16 | 1.514 (14) |
C7—C8 | 1.494 (14) | C15—H15A | 0.9700 |
C7—H7A | 0.9700 | C15—H15B | 0.9700 |
C7—H7B | 0.9700 | C16—C17 | 1.554 (14) |
C8—C9 | 1.504 (14) | C16—H16A | 0.9700 |
C8—H8A | 0.9700 | C16—H16B | 0.9700 |
C8—H8B | 0.9700 | C17—C18 | 1.468 (15) |
C9—C10 | 1.535 (18) | C17—H17A | 0.9700 |
C9—H9A | 0.9700 | C17—H17B | 0.9700 |
C9—H9B | 0.9700 | C18—H18A | 0.9600 |
C10—H10A | 0.9600 | C18—H18B | 0.9600 |
C10—H10B | 0.9600 | C18—H18C | 0.9600 |
C11—Sn1—C15 | 124.9 (5) | H10A—C10—H10B | 109.5 |
C11—Sn1—C7 | 116.3 (6) | C9—C10—H10C | 109.5 |
C15—Sn1—C7 | 116.4 (6) | H10A—C10—H10C | 109.5 |
C11—Sn1—O1 | 97.9 (5) | H10B—C10—H10C | 109.5 |
C15—Sn1—O1 | 95.9 (6) | H10D—C10'—H10E | 109.5 |
C7—Sn1—O1 | 91.2 (5) | H10D—C10'—H10F | 109.5 |
C11—Sn1—N1i | 81.4 (5) | H10E—C10'—H10F | 109.5 |
C15—Sn1—N1i | 85.0 (6) | C12—C11—Sn1 | 120.1 (9) |
C7—Sn1—N1i | 88.5 (5) | C12—C11—H11A | 107.3 |
O1—Sn1—N1i | 179.1 (8) | Sn1—C11—H11A | 107.3 |
C11—Sn1—O2 | 80.8 (4) | C12—C11—H11B | 107.3 |
C15—Sn1—O2 | 73.3 (4) | Sn1—C11—H11B | 107.3 |
C7—Sn1—O2 | 135.2 (4) | H11A—C11—H11B | 106.9 |
O1—Sn1—O2 | 44.1 (3) | C11—C12—C13 | 113.4 (12) |
N1i—Sn1—O2 | 136.2 (3) | C11—C12—H12A | 108.9 |
C6—O1—Sn1 | 120.1 (9) | C13—C12—H12A | 108.9 |
C6—O2—Sn1 | 70.8 (7) | C11—C12—H12B | 108.9 |
C1—N1—C5 | 117.1 (14) | C13—C12—H12B | 108.9 |
N1—C1—C2 | 125.2 (12) | H12A—C12—H12B | 107.7 |
N1—C1—H1 | 117.4 | C14—C13—C12 | 115.6 (17) |
C2—C1—H1 | 117.4 | C14—C13—H13A | 108.4 |
C1—C2—C3 | 117.7 (11) | C12—C13—H13A | 108.4 |
C1—C2—H2 | 121.2 | C14—C13—H13B | 108.4 |
C3—C2—H2 | 121.2 | C12—C13—H13B | 108.4 |
C4—C3—C2 | 117.4 (10) | H13A—C13—H13B | 107.4 |
C4—C3—C6 | 122.8 (10) | H13C—C13'—H13D | 107.3 |
C2—C3—C6 | 119.7 (10) | C13—C14—H14A | 109.5 |
C3—C4—C5 | 120.4 (11) | C13—C14—H14B | 109.5 |
C3—C4—H4 | 119.8 | H14A—C14—H14B | 109.5 |
C5—C4—H4 | 119.8 | C13—C14—H14C | 109.5 |
N1—C5—C4 | 122.1 (12) | H14A—C14—H14C | 109.5 |
N1—C5—H5 | 119.0 | H14B—C14—H14C | 109.5 |
C4—C5—H5 | 119.0 | C16—C15—Sn1 | 115.8 (9) |
O2—C6—O1 | 125.0 (12) | C16—C15—H15A | 108.3 |
O2—C6—C3 | 119.9 (11) | Sn1—C15—H15A | 108.3 |
O1—C6—C3 | 115.1 (10) | C16—C15—H15B | 108.3 |
C8—C7—Sn1 | 116.5 (10) | Sn1—C15—H15B | 108.3 |
C8—C7—H7A | 108.2 | H15A—C15—H15B | 107.4 |
Sn1—C7—H7A | 108.2 | C15—C16—C17 | 109.7 (11) |
C8—C7—H7B | 108.2 | C15—C16—H16A | 109.7 |
Sn1—C7—H7B | 108.2 | C17—C16—H16A | 109.7 |
H7A—C7—H7B | 107.3 | C15—C16—H16B | 109.7 |
C7—C8—C9 | 116.3 (12) | C17—C16—H16B | 109.7 |
C7—C8—H8A | 108.2 | H16A—C16—H16B | 108.2 |
C9—C8—H8A | 108.2 | C18—C17—C16 | 114.1 (13) |
C7—C8—H8B | 108.2 | C18—C17—H17A | 108.7 |
C9—C8—H8B | 108.2 | C16—C17—H17A | 108.7 |
H8A—C8—H8B | 107.4 | C18—C17—H17B | 108.7 |
C8—C9—C10 | 112.0 (16) | C16—C17—H17B | 108.7 |
C8—C9—H9A | 109.2 | H17A—C17—H17B | 107.6 |
C10—C9—H9A | 109.2 | C17—C18—H18A | 109.5 |
C8—C9—H9B | 109.2 | C17—C18—H18B | 109.5 |
C10—C9—H9B | 109.2 | H18A—C18—H18B | 109.5 |
H9A—C9—H9B | 107.9 | C17—C18—H18C | 109.5 |
C9—C10—H10A | 109.5 | H18A—C18—H18C | 109.5 |
C9—C10—H10B | 109.5 | H18B—C18—H18C | 109.5 |
Symmetry code: (i) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Sn(C4H9)3(C6H4NO2)] |
Mr | 412.13 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 298 |
a, b, c (Å) | 9.594 (4), 24.286 (11), 9.715 (4) |
β (°) | 114.864 (5) |
V (Å3) | 2053.7 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.25 |
Crystal size (mm) | 0.53 × 0.46 × 0.41 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.529, 0.597 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5123, 3260, 2741 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.163, 1.00 |
No. of reflections | 3260 |
No. of parameters | 219 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.41, −0.73 |
Absolute structure | Flack (1983), 1798 Friedel pairs |
Absolute structure parameter | 0.06 (10) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXL97.
Sn1—C11 | 2.099 (12) | Sn1—N1i | 2.603 (16) |
Sn1—C15 | 2.112 (13) | Sn1—O2 | 3.186 (9) |
Sn1—C7 | 2.127 (13) | ||
C11—Sn1—C15 | 124.9 (5) | O1—Sn1—N1i | 179.1 (8) |
C11—Sn1—C7 | 116.3 (6) | C11—Sn1—O2 | 80.8 (4) |
C15—Sn1—C7 | 116.4 (6) | C15—Sn1—O2 | 73.3 (4) |
C11—Sn1—O1 | 97.9 (5) | C7—Sn1—O2 | 135.2 (4) |
C15—Sn1—O1 | 95.9 (6) | O1—Sn1—O2 | 44.1 (3) |
C7—Sn1—O1 | 91.2 (5) | N1i—Sn1—O2 | 136.2 (3) |
C11—Sn1—N1i | 81.4 (5) | C6—O1—Sn1 | 120.1 (9) |
C15—Sn1—N1i | 85.0 (6) | C6—O2—Sn1 | 70.8 (7) |
C7—Sn1—N1i | 88.5 (5) |
Symmetry code: (i) x, y, z−1. |
Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities as well as their industrial and agricultural applications (Gielen et al., 1988). pyridine-3-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures.
The asymmetric unit of the title compound, (I), (Fig. 1), consists of three butyl and one (pyridine-3-carboxylate) groups bonded to the tin atom, where the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
The tin atom has a distorted trigonal bipyramidal geometry with atoms O1 and N1i of the pyridine-3-carboxylic acid [symmetry code: (i) x, y, z - 1], in axial and C atoms of the three butyl groups in equatorial positions, as in the similar compound (Ma et al., 2004).
In the crystal structure, (Fig. 2), the molecules are linked to form an infinite one-dimensional polymeric chain structure.