Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102007539/fg1647sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102007539/fg1647Isup2.hkl |
CCDC reference: 188596
N-(1-Naphthyl)maleamic acid was prepared by adding 1-naphthylamine (8.59 g, 0.06 mole) to a solution containing an equimolar quantity of maleic anhydride (5.88 g, 0.06 mol) in glacial acetic acid (100 ml). The reaction mixture was stirred for 1 h, which afforded a yellow solid. The yellow product was washed with water, dried and recrystallized from ethanol–water (m.p. 421–422 K). The silver salt of N-(1-naphthyl)maleamic acid was prepared by dissolving the acid (4.82 g, 0.02 mol) in ethanol (200 ml) and adding to it a solution of an equimolar quantity of sodium bicarbonate (1.68 g, 0.02 mol). A solution of silver nitrate (3.397 g, 0.02 mol) was added dropwise to the above mixture. The precipitates thus formed were filtered off under suction, washed with water and dried over anhydrous calcium chloride in the dark. The silver salt (1.735 g, 0.005 mol) was suspended in dry chloroform (50 ml) in a 250 ml two-neck round-bottomed flask equipped with a magnetic stirrer bar and a condenser. Tributyltin chloride (1.22 ml, 0.005 mol) was added slowly with constant stirring. The reaction mixture was refluxed for 8 h under an inert atmosphere. Silver chloride which formed during the reaction was removed by filtration and the solvent was evaporated under reduced pressure. Purified (I) was obtained by crystallization of the product from chloroform–n-hexane (1:1) at room temperature by slow evaporation.
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with displacement ellipsoids plotted at the 50% probability level. [Symmetry codes: (i) x + 1, y, z; (ii) x - 1, y, z.] |
C26H37NO3Sn | Z = 2 |
Mr = 530.26 | F(000) = 548 |
Triclinic, P1 | Dx = 1.377 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5705 (7) Å | Cell parameters from 8025 reflections |
b = 11.7377 (9) Å | θ = 1.0–25.0° |
c = 12.4726 (11) Å | µ = 1.02 mm−1 |
α = 97.011 (3)° | T = 170 K |
β = 107.571 (4)° | Block, yellow |
γ = 102.297 (6)° | 0.15 × 0.10 × 0.08 mm |
V = 1278.71 (18) Å3 |
Nonius KappaCCD diffractometer | 4329 independent reflections |
Radiation source: fine-focus sealed tube | 3640 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω and ϕ scans | θmax = 25.0°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV: Blessing, 1997) | h = −11→11 |
Tmin = 0.861, Tmax = 0.922 | k = −13→13 |
8025 measured reflections | l = −14→14 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0842P)2 + 3.9999P] where P = (Fo2 + 2Fc2)/3 |
4329 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 1.80 e Å−3 |
0 restraints | Δρmin = −1.43 e Å−3 |
C26H37NO3Sn | γ = 102.297 (6)° |
Mr = 530.26 | V = 1278.71 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.5705 (7) Å | Mo Kα radiation |
b = 11.7377 (9) Å | µ = 1.02 mm−1 |
c = 12.4726 (11) Å | T = 170 K |
α = 97.011 (3)° | 0.15 × 0.10 × 0.08 mm |
β = 107.571 (4)° |
Nonius KappaCCD diffractometer | 4329 independent reflections |
Absorption correction: multi-scan (SORTAV: Blessing, 1997) | 3640 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 0.922 | Rint = 0.035 |
8025 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.13 | Δρmax = 1.80 e Å−3 |
4329 reflections | Δρmin = −1.43 e Å−3 |
280 parameters |
Refinement. The H atoms were located from difference Fourier syntheses and were included in the refinements at idealized positions with isotropic displacement parameters 1.5 (methyl) and 1.2 (non-methyl) times the equivalent displacement parameters of the atoms to which they were bonded. The final difference map was free of any chemically significant features with some electron density in the vicinity of the Sn atom. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.22096 (5) | 0.23271 (4) | 0.55844 (4) | 0.0376 (2) | |
O1 | −0.0238 (5) | 0.1951 (4) | 0.4825 (5) | 0.0463 (12) | |
O2 | −0.0329 (5) | 0.3347 (5) | 0.6164 (5) | 0.0498 (13) | |
O3 | −0.5023 (5) | 0.2679 (4) | 0.6421 (4) | 0.0420 (11) | |
N1 | −0.2518 (6) | 0.3604 (5) | 0.7011 (5) | 0.0387 (13) | |
H1 | −0.1686 | 0.3661 | 0.6833 | 0.046* | |
C1 | 0.2107 (8) | 0.0846 (6) | 0.4366 (6) | 0.0429 (17) | |
H1A | 0.3064 | 0.0604 | 0.4634 | 0.051* | |
H1B | 0.1264 | 0.0171 | 0.4332 | 0.051* | |
C2 | 0.1872 (8) | 0.1093 (7) | 0.3157 (7) | 0.0486 (18) | |
H2A | 0.0917 | 0.1337 | 0.2891 | 0.058* | |
H2B | 0.2716 | 0.1769 | 0.3193 | 0.058* | |
C3 | 0.1797 (9) | 0.0041 (8) | 0.2278 (8) | 0.062 (2) | |
H3A | 0.1044 | −0.0665 | 0.2311 | 0.075* | |
H3B | 0.1433 | 0.0220 | 0.1501 | 0.075* | |
C4 | 0.3301 (9) | −0.0257 (8) | 0.2456 (8) | 0.056 (2) | |
H4A | 0.3169 | −0.0944 | 0.1868 | 0.084* | |
H4B | 0.3664 | −0.0447 | 0.3218 | 0.084* | |
H4C | 0.4045 | 0.0428 | 0.2396 | 0.084* | |
C5 | 0.2702 (8) | 0.4026 (6) | 0.5116 (7) | 0.0443 (17) | |
H5A | 0.3051 | 0.3926 | 0.4449 | 0.053* | |
H5B | 0.1739 | 0.4261 | 0.4857 | 0.053* | |
C6 | 0.3875 (9) | 0.5052 (7) | 0.6027 (7) | 0.0498 (19) | |
H6A | 0.4801 | 0.4789 | 0.6362 | 0.060* | |
H6B | 0.4156 | 0.5717 | 0.5649 | 0.060* | |
C7 | 0.3374 (11) | 0.5513 (8) | 0.6985 (8) | 0.063 (2) | |
H7A | 0.3140 | 0.4864 | 0.7393 | 0.076* | |
H7B | 0.2428 | 0.5754 | 0.6656 | 0.076* | |
C8 | 0.4563 (12) | 0.6566 (8) | 0.7840 (8) | 0.074 (3) | |
H8A | 0.4167 | 0.6846 | 0.8432 | 0.111* | |
H8B | 0.4806 | 0.7210 | 0.7440 | 0.111* | |
H8C | 0.5484 | 0.6322 | 0.8199 | 0.111* | |
C9 | 0.2300 (8) | 0.1950 (7) | 0.7226 (7) | 0.0462 (18) | |
H9A | 0.3045 | 0.2616 | 0.7829 | 0.055* | |
H9B | 0.1292 | 0.1885 | 0.7311 | 0.055* | |
C10 | 0.2756 (9) | 0.0788 (7) | 0.7390 (7) | 0.0523 (19) | |
H10A | 0.2034 | 0.0142 | 0.6755 | 0.063* | |
H10B | 0.3774 | 0.0875 | 0.7319 | 0.063* | |
C11 | 0.2802 (12) | 0.0409 (9) | 0.8495 (9) | 0.075 (3) | |
H11A | 0.1773 | 0.0285 | 0.8553 | 0.091* | |
H11B | 0.3054 | −0.0367 | 0.8476 | 0.091* | |
C12 | 0.3876 (17) | 0.1233 (11) | 0.9519 (10) | 0.102 (4) | |
H12A | 0.3820 | 0.0913 | 1.0199 | 0.153* | |
H12B | 0.3626 | 0.2002 | 0.9560 | 0.153* | |
H12C | 0.4906 | 0.1342 | 0.9489 | 0.153* | |
C13 | −0.0952 (7) | 0.2523 (6) | 0.5332 (7) | 0.0416 (16) | |
C14 | −0.2644 (7) | 0.2095 (6) | 0.4770 (6) | 0.0417 (16) | |
H14 | −0.2976 | 0.1644 | 0.4011 | 0.050* | |
C15 | −0.3749 (7) | 0.2241 (6) | 0.5157 (6) | 0.0403 (16) | |
H15 | −0.4731 | 0.1864 | 0.4614 | 0.048* | |
C16 | −0.3797 (7) | 0.2864 (6) | 0.6255 (6) | 0.0362 (15) | |
C17 | −0.2369 (8) | 0.4304 (6) | 0.8064 (6) | 0.0397 (16) | |
C18 | −0.3221 (9) | 0.3905 (7) | 0.8721 (7) | 0.0490 (18) | |
H18 | −0.3943 | 0.3149 | 0.8459 | 0.059* | |
C19 | −0.3030 (10) | 0.4605 (8) | 0.9775 (7) | 0.058 (2) | |
H19 | −0.3652 | 0.4329 | 1.0207 | 0.069* | |
C20 | −0.1983 (11) | 0.5661 (8) | 1.0186 (7) | 0.059 (2) | |
H20 | −0.1847 | 0.6104 | 1.0917 | 0.070* | |
C21 | −0.1082 (9) | 0.6121 (7) | 0.9542 (7) | 0.0482 (18) | |
C22 | −0.0005 (10) | 0.7234 (8) | 0.9929 (8) | 0.061 (2) | |
H22 | 0.0131 | 0.7698 | 1.0650 | 0.073* | |
C23 | 0.0842 (11) | 0.7662 (8) | 0.9303 (8) | 0.063 (2) | |
H23 | 0.1562 | 0.8418 | 0.9586 | 0.076* | |
C24 | 0.0662 (10) | 0.6995 (7) | 0.8240 (7) | 0.053 (2) | |
H24 | 0.1254 | 0.7300 | 0.7799 | 0.064* | |
C25 | −0.0363 (8) | 0.5905 (7) | 0.7835 (7) | 0.0453 (17) | |
H25 | −0.0471 | 0.5459 | 0.7112 | 0.054* | |
C26 | −0.1263 (8) | 0.5430 (6) | 0.8461 (6) | 0.0407 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0266 (3) | 0.0457 (3) | 0.0427 (3) | 0.01165 (19) | 0.0152 (2) | 0.0041 (2) |
O1 | 0.030 (2) | 0.055 (3) | 0.053 (3) | 0.013 (2) | 0.016 (2) | −0.001 (2) |
O2 | 0.026 (2) | 0.058 (3) | 0.059 (3) | 0.009 (2) | 0.014 (2) | −0.010 (3) |
O3 | 0.023 (2) | 0.057 (3) | 0.047 (3) | 0.013 (2) | 0.014 (2) | 0.006 (2) |
N1 | 0.029 (3) | 0.047 (3) | 0.044 (3) | 0.013 (2) | 0.018 (3) | 0.007 (3) |
C1 | 0.032 (4) | 0.046 (4) | 0.047 (4) | 0.009 (3) | 0.015 (3) | −0.002 (3) |
C2 | 0.036 (4) | 0.066 (5) | 0.046 (4) | 0.027 (3) | 0.012 (3) | 0.001 (4) |
C3 | 0.043 (4) | 0.077 (6) | 0.055 (5) | 0.021 (4) | 0.007 (4) | −0.012 (4) |
C4 | 0.047 (4) | 0.065 (5) | 0.058 (5) | 0.022 (4) | 0.023 (4) | −0.005 (4) |
C5 | 0.038 (4) | 0.049 (4) | 0.051 (5) | 0.016 (3) | 0.018 (3) | 0.015 (3) |
C6 | 0.048 (4) | 0.042 (4) | 0.062 (5) | 0.012 (3) | 0.020 (4) | 0.016 (4) |
C7 | 0.070 (6) | 0.053 (5) | 0.062 (6) | 0.003 (4) | 0.029 (5) | 0.007 (4) |
C8 | 0.093 (7) | 0.055 (5) | 0.062 (6) | 0.003 (5) | 0.023 (5) | 0.005 (4) |
C9 | 0.032 (4) | 0.064 (5) | 0.050 (5) | 0.015 (3) | 0.022 (3) | 0.010 (4) |
C10 | 0.046 (4) | 0.057 (5) | 0.060 (5) | 0.021 (4) | 0.020 (4) | 0.017 (4) |
C11 | 0.073 (6) | 0.076 (6) | 0.076 (7) | 0.024 (5) | 0.018 (5) | 0.023 (5) |
C12 | 0.131 (11) | 0.094 (9) | 0.074 (8) | 0.025 (8) | 0.023 (8) | 0.030 (7) |
C13 | 0.025 (3) | 0.050 (4) | 0.048 (4) | 0.011 (3) | 0.013 (3) | 0.003 (3) |
C14 | 0.028 (3) | 0.052 (4) | 0.040 (4) | 0.009 (3) | 0.009 (3) | −0.001 (3) |
C15 | 0.021 (3) | 0.050 (4) | 0.046 (4) | 0.011 (3) | 0.007 (3) | 0.002 (3) |
C16 | 0.025 (3) | 0.043 (4) | 0.042 (4) | 0.014 (3) | 0.010 (3) | 0.009 (3) |
C17 | 0.035 (4) | 0.051 (4) | 0.040 (4) | 0.021 (3) | 0.014 (3) | 0.011 (3) |
C18 | 0.045 (4) | 0.060 (5) | 0.047 (5) | 0.015 (4) | 0.022 (4) | 0.012 (4) |
C19 | 0.056 (5) | 0.078 (6) | 0.050 (5) | 0.024 (4) | 0.027 (4) | 0.017 (4) |
C20 | 0.071 (6) | 0.075 (6) | 0.040 (5) | 0.034 (5) | 0.025 (4) | 0.009 (4) |
C21 | 0.051 (4) | 0.051 (4) | 0.040 (4) | 0.020 (4) | 0.009 (4) | 0.002 (3) |
C22 | 0.068 (6) | 0.057 (5) | 0.045 (5) | 0.018 (4) | 0.003 (4) | 0.001 (4) |
C23 | 0.065 (6) | 0.053 (5) | 0.055 (5) | 0.005 (4) | 0.008 (4) | 0.004 (4) |
C24 | 0.056 (5) | 0.053 (5) | 0.044 (5) | 0.011 (4) | 0.008 (4) | 0.011 (4) |
C25 | 0.043 (4) | 0.048 (4) | 0.039 (4) | 0.011 (3) | 0.007 (3) | 0.005 (3) |
C26 | 0.035 (4) | 0.047 (4) | 0.041 (4) | 0.019 (3) | 0.008 (3) | 0.009 (3) |
Sn1—C1 | 2.129 (7) | C9—C10 | 1.537 (11) |
Sn1—C9 | 2.127 (8) | C9—H9A | 0.9900 |
Sn1—C5 | 2.142 (7) | C9—H9B | 0.9900 |
Sn1—O1 | 2.167 (5) | C10—C11 | 1.490 (13) |
Sn1—O3i | 2.457 (4) | C10—H10A | 0.9900 |
O1—C13 | 1.293 (8) | C10—H10B | 0.9900 |
O2—C13 | 1.226 (9) | C11—C12 | 1.451 (15) |
O3—C16 | 1.231 (8) | C11—H11A | 0.9900 |
O3—Sn1ii | 2.457 (4) | C11—H11B | 0.9900 |
N1—C16 | 1.339 (9) | C12—H12A | 0.9800 |
N1—C17 | 1.412 (9) | C12—H12B | 0.9800 |
N1—H1 | 0.8800 | C12—H12C | 0.9800 |
C1—C2 | 1.529 (11) | C13—C14 | 1.499 (9) |
C1—H1A | 0.9900 | C14—C15 | 1.321 (10) |
C1—H1B | 0.9900 | C14—H14 | 0.9500 |
C2—C3 | 1.521 (11) | C15—C16 | 1.491 (10) |
C2—H2A | 0.9900 | C15—H15 | 0.9500 |
C2—H2B | 0.9900 | C17—C18 | 1.375 (10) |
C3—C4 | 1.511 (11) | C17—C26 | 1.429 (10) |
C3—H3A | 0.9900 | C18—C19 | 1.402 (12) |
C3—H3B | 0.9900 | C18—H18 | 0.9500 |
C4—H4A | 0.9800 | C19—C20 | 1.345 (13) |
C4—H4B | 0.9800 | C19—H19 | 0.9500 |
C4—H4C | 0.9800 | C20—C21 | 1.416 (12) |
C5—C6 | 1.524 (11) | C20—H20 | 0.9500 |
C5—H5A | 0.9900 | C21—C22 | 1.405 (12) |
C5—H5B | 0.9900 | C21—C26 | 1.428 (10) |
C6—C7 | 1.499 (12) | C22—C23 | 1.350 (13) |
C6—H6A | 0.9900 | C22—H22 | 0.9500 |
C6—H6B | 0.9900 | C23—C24 | 1.397 (12) |
C7—C8 | 1.519 (12) | C23—H23 | 0.9500 |
C7—H7A | 0.9900 | C24—C25 | 1.364 (11) |
C7—H7B | 0.9900 | C24—H24 | 0.9500 |
C8—H8A | 0.9800 | C25—C26 | 1.403 (10) |
C8—H8B | 0.9800 | C25—H25 | 0.9500 |
C8—H8C | 0.9800 | ||
C1—Sn1—C9 | 114.5 (3) | Sn1—C9—H9A | 109.3 |
C1—Sn1—C5 | 115.5 (3) | C10—C9—H9B | 109.3 |
C9—Sn1—C5 | 128.5 (3) | Sn1—C9—H9B | 109.3 |
C1—Sn1—O1 | 87.8 (2) | H9A—C9—H9B | 108.0 |
C9—Sn1—O1 | 97.8 (2) | C11—C10—C9 | 116.4 (8) |
C5—Sn1—O1 | 95.8 (2) | C11—C10—H10A | 108.2 |
C1—Sn1—O3i | 90.3 (2) | C9—C10—H10A | 108.2 |
C9—Sn1—O3i | 82.1 (2) | C11—C10—H10B | 108.2 |
C5—Sn1—O3i | 85.8 (2) | C9—C10—H10B | 108.2 |
O1—Sn1—O3i | 177.97 (17) | H10A—C10—H10B | 107.3 |
C13—O1—Sn1 | 118.6 (4) | C12—C11—C10 | 115.3 (9) |
C16—O3—Sn1ii | 147.0 (5) | C12—C11—H11A | 108.4 |
C16—N1—C17 | 126.6 (6) | C10—C11—H11A | 108.4 |
C16—N1—H1 | 116.7 | C12—C11—H11B | 108.4 |
C17—N1—H1 | 116.7 | C10—C11—H11B | 108.4 |
C2—C1—Sn1 | 113.9 (5) | H11A—C11—H11B | 107.5 |
C2—C1—H1A | 108.8 | C11—C12—H12A | 109.5 |
Sn1—C1—H1A | 108.8 | C11—C12—H12B | 109.5 |
C2—C1—H1B | 108.8 | H12A—C12—H12B | 109.5 |
Sn1—C1—H1B | 108.8 | C11—C12—H12C | 109.5 |
H1A—C1—H1B | 107.7 | H12A—C12—H12C | 109.5 |
C3—C2—C1 | 114.4 (7) | H12B—C12—H12C | 109.5 |
C3—C2—H2A | 108.7 | O2—C13—O1 | 124.3 (6) |
C1—C2—H2A | 108.7 | O2—C13—C14 | 123.0 (6) |
C3—C2—H2B | 108.7 | O1—C13—C14 | 112.7 (6) |
C1—C2—H2B | 108.7 | C15—C14—C13 | 130.7 (7) |
H2A—C2—H2B | 107.6 | C15—C14—H14 | 114.6 |
C4—C3—C2 | 113.7 (7) | C13—C14—H14 | 114.6 |
C4—C3—H3A | 108.8 | C14—C15—C16 | 134.2 (6) |
C2—C3—H3A | 108.8 | C14—C15—H15 | 112.9 |
C4—C3—H3B | 108.8 | C16—C15—H15 | 112.9 |
C2—C3—H3B | 108.8 | O3—C16—N1 | 123.0 (6) |
H3A—C3—H3B | 107.7 | O3—C16—C15 | 118.1 (6) |
C3—C4—H4A | 109.5 | N1—C16—C15 | 119.0 (6) |
C3—C4—H4B | 109.5 | C18—C17—N1 | 121.5 (7) |
H4A—C4—H4B | 109.5 | C18—C17—C26 | 120.1 (7) |
C3—C4—H4C | 109.5 | N1—C17—C26 | 118.4 (6) |
H4A—C4—H4C | 109.5 | C17—C18—C19 | 120.4 (8) |
H4B—C4—H4C | 109.5 | C17—C18—H18 | 119.8 |
C6—C5—Sn1 | 117.7 (5) | C19—C18—H18 | 119.8 |
C6—C5—H5A | 107.9 | C20—C19—C18 | 121.2 (8) |
Sn1—C5—H5A | 107.9 | C20—C19—H19 | 119.4 |
C6—C5—H5B | 107.9 | C18—C19—H19 | 119.4 |
Sn1—C5—H5B | 107.9 | C19—C20—C21 | 120.8 (8) |
H5A—C5—H5B | 107.2 | C19—C20—H20 | 119.6 |
C7—C6—C5 | 115.2 (7) | C21—C20—H20 | 119.6 |
C7—C6—H6A | 108.5 | C22—C21—C20 | 122.5 (8) |
C5—C6—H6A | 108.5 | C22—C21—C26 | 118.4 (8) |
C7—C6—H6B | 108.5 | C20—C21—C26 | 119.1 (7) |
C5—C6—H6B | 108.5 | C23—C22—C21 | 121.8 (8) |
H6A—C6—H6B | 107.5 | C23—C22—H22 | 119.1 |
C6—C7—C8 | 112.8 (8) | C21—C22—H22 | 119.1 |
C6—C7—H7A | 109.0 | C22—C23—C24 | 120.1 (8) |
C8—C7—H7A | 109.0 | C22—C23—H23 | 120.0 |
C6—C7—H7B | 109.0 | C24—C23—H23 | 120.0 |
C8—C7—H7B | 109.0 | C25—C24—C23 | 120.1 (8) |
H7A—C7—H7B | 107.8 | C25—C24—H24 | 119.9 |
C7—C8—H8A | 109.5 | C23—C24—H24 | 119.9 |
C7—C8—H8B | 109.5 | C24—C25—C26 | 121.4 (7) |
H8A—C8—H8B | 109.5 | C24—C25—H25 | 119.3 |
C7—C8—H8C | 109.5 | C26—C25—H25 | 119.3 |
H8A—C8—H8C | 109.5 | C25—C26—C21 | 118.2 (7) |
H8B—C8—H8C | 109.5 | C25—C26—C17 | 123.5 (7) |
C10—C9—Sn1 | 111.6 (5) | C21—C26—C17 | 118.3 (7) |
C10—C9—H9A | 109.3 | ||
C1—Sn1—O1—C13 | 171.1 (6) | C17—N1—C16—O3 | −2.4 (11) |
C9—Sn1—O1—C13 | 56.7 (6) | C17—N1—C16—C15 | 177.0 (6) |
C5—Sn1—O1—C13 | −73.5 (6) | C14—C15—C16—O3 | −168.7 (8) |
C9—Sn1—C1—C2 | 173.8 (5) | C14—C15—C16—N1 | 11.9 (12) |
C5—Sn1—C1—C2 | −19.2 (6) | C16—N1—C17—C18 | 34.8 (11) |
O1—Sn1—C1—C2 | 76.2 (5) | C16—N1—C17—C26 | −147.5 (7) |
O3i—Sn1—C1—C2 | −104.7 (5) | N1—C17—C18—C19 | 178.7 (7) |
Sn1—C1—C2—C3 | −180.0 (5) | C26—C17—C18—C19 | 1.0 (11) |
C1—C2—C3—C4 | −70.2 (10) | C17—C18—C19—C20 | −2.1 (13) |
C1—Sn1—C5—C6 | −134.8 (5) | C18—C19—C20—C21 | 2.6 (13) |
C9—Sn1—C5—C6 | 30.0 (7) | C19—C20—C21—C22 | 178.3 (8) |
O1—Sn1—C5—C6 | 134.8 (5) | C19—C20—C21—C26 | −2.0 (12) |
O3i—Sn1—C5—C6 | −46.5 (5) | C20—C21—C22—C23 | −179.8 (8) |
Sn1—C5—C6—C7 | −71.0 (8) | C26—C21—C22—C23 | 0.5 (13) |
C5—C6—C7—C8 | −177.7 (7) | C21—C22—C23—C24 | 0.0 (14) |
C1—Sn1—C9—C10 | 17.1 (6) | C22—C23—C24—C25 | −0.4 (14) |
C5—Sn1—C9—C10 | −147.8 (5) | C23—C24—C25—C26 | 0.4 (12) |
O1—Sn1—C9—C10 | 108.3 (5) | C24—C25—C26—C21 | 0.2 (11) |
O3i—Sn1—C9—C10 | −69.6 (5) | C24—C25—C26—C17 | 178.9 (7) |
Sn1—C9—C10—C11 | −177.8 (6) | C22—C21—C26—C25 | −0.6 (10) |
C9—C10—C11—C12 | −61.2 (13) | C20—C21—C26—C25 | 179.7 (7) |
Sn1—O1—C13—O2 | 6.8 (10) | C22—C21—C26—C17 | −179.4 (7) |
Sn1—O1—C13—C14 | −174.8 (5) | C20—C21—C26—C17 | 0.9 (10) |
O2—C13—C14—C15 | −19.2 (13) | C18—C17—C26—C25 | −179.2 (7) |
O1—C13—C14—C15 | 162.4 (8) | N1—C17—C26—C25 | 3.1 (10) |
C13—C14—C15—C16 | 0.4 (15) | C18—C17—C26—C21 | −0.4 (10) |
Sn1ii—O3—C16—N1 | 142.2 (7) | N1—C17—C26—C21 | −178.2 (6) |
Sn1ii—O3—C16—C15 | −37.2 (11) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C26H37NO3Sn |
Mr | 530.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 170 |
a, b, c (Å) | 9.5705 (7), 11.7377 (9), 12.4726 (11) |
α, β, γ (°) | 97.011 (3), 107.571 (4), 102.297 (6) |
V (Å3) | 1278.71 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.02 |
Crystal size (mm) | 0.15 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV: Blessing, 1997) |
Tmin, Tmax | 0.861, 0.922 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8025, 4329, 3640 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.169, 1.13 |
No. of reflections | 4329 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.80, −1.43 |
Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
Sn1—C1 | 2.129 (7) | O1—C13 | 1.293 (8) |
Sn1—C9 | 2.127 (8) | O2—C13 | 1.226 (9) |
Sn1—C5 | 2.142 (7) | O3—C16 | 1.231 (8) |
Sn1—O1 | 2.167 (5) | N1—C16 | 1.339 (9) |
Sn1—O3i | 2.457 (4) | N1—C17 | 1.412 (9) |
C1—Sn1—C9 | 114.5 (3) | C9—Sn1—O3i | 82.1 (2) |
C1—Sn1—C5 | 115.5 (3) | C5—Sn1—O3i | 85.8 (2) |
C9—Sn1—C5 | 128.5 (3) | O1—Sn1—O3i | 177.97 (17) |
C1—Sn1—O1 | 87.8 (2) | C13—O1—Sn1 | 118.6 (4) |
C9—Sn1—O1 | 97.8 (2) | C16—O3—Sn1ii | 147.0 (5) |
C5—Sn1—O1 | 95.8 (2) | C16—N1—C17 | 126.6 (6) |
C1—Sn1—O3i | 90.3 (2) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
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There have been several reports dealing with the impact of organotin chemistry in the biosphere (Gielen, 1994; Ng et al., 1991). The exploration of the structure–activity relationships of such systems has led to numerous reports in recent years (Gielen et al., 1994; Selvaratnam et al., 1994; McManus et al., 1994). Furthermore, the structural chemistry of organotin compounds with a coordination number higher than four is being extensively studied because of their biological activity, enhanced reactivity and stereochemical non-rigidity (Mehring et al., 1998). Our contributions in this field have been related to the synthesis and structural characterization of organotin derivatives of donor ligands containing chalcogens, with special reference to their biological applications (Badshah et al., 1994; Danish et al., 1995; Ali et al., 1993; Choudhary et al., 2001; Bhatti et al., 2000). In a continuation of our studies on the structural chemistry of organotin carboxylates (Parvez, Ali, Mazhar, Bhatti & Khokhar, 1999; Parvez, Ali, Mazhar, Bhatti & Choudhary. 1999; Parvez et al., 2000), we have prepared catena-poly[[tri-n-butyltin]-µ-N-(1-naphthyl)maleamato], (I), the crystal structure of which is reported in this paper.
The structure of (I) (Fig. 1) is composed of polymeric chains wherein O atoms of both ends of the N-(1-naphthyl)maleamate ligand coordinate the Sn atoms of the trigonal-planar tri-n-butyltin moiety. The Sn—C distances are identical within 3σ limits [mean Sn—C 2.133 (7) Å]. On the other hand, the Sn—O1 and Sn—O3 distances are significantly different from each other, with values of 2.167 (4) and 2.457 (4) Å, respectively, indicating that the former is a covalent bond and the latter is a coordinate bond. The Sn atom has a distorted trigonal-bipyramidal geometry, with the Sn atom 0.153 (2) Å out of the equatorial plane formed by the three C atoms bonded to it, towards the more strongly bonded O1 atom. The O1—Sn1—O3 angle is almost linear [177.97 (17)°], the C—Sn—C angles deviate somewhat from the ideal value of 120° [range 114.5 (3)–128.5 (3)°] and the O—Sn—C angles lie in the range 82.1 (2)–97.8 (2)°. These bond distances and angles are in agreement with the corresponding values found for similar Sn complexes contained in the Cambridge Structural Database (Allen & Kennard, 1993).
The molecular dimensions in the N-(1-naphthyl)maleamate ligand are normal. The ligand forms an essentially planar seven-membered ring involving an intramolecular N—H···O hydrogen bond [H1···O2 and N1···O1 1.82 and 2.669 (7) Å, respectively, and N—H···O 162°]. In terms of graph-set representation (Bernstein et al., 1994), this ring exhibits a S(7) hydrogen-bond pattern.