catena-Poly[dicyclohexylammonium [tributyltin-
-(4-oxo-4
H-pyran-2,6-dicarboxylato-
O2:
O6)]], (C
12H
24N)[Sn(C
7H
2O
6)(C
4H
9)
3], consists of 4-oxo-4
H-pyran-2,6-dicarboxylato groups that axially link adjacent tributyltin units into a linear polyanionic chain. The ammonium counter-ions surround the chain, and each cation forms a pair of hydrogen bonds to the double-bond carbonyl O atoms of the same dianionic group. The chain propagates in a zigzag manner along the
c axis of the monoclinic cell. In
catena-poly[methyl(phenyl)ammonium [tributyltin-
-(pyridine-2,6-dicarboxylato-
O2:
O6)]], (C
7H
10N)[Sn(C
7H
3NO
4)(C
4H
9)
3], the pyridine-2,6-dicarboxylato groups also link the tributyltin groups into a chain, but the hydrogen-bonded chain propagates linearly on the
ac face of the monoclinic cell.
Supporting information
CCDC references: 150325; 150326
Dicyclohexylamine (1.81 g, 10 mmol) and 4-oxo-4H-pyran-2,6-dicarboxylic (chelidonic) acid (1.84 g, 10 mol) were heated in a small volume of ethanol until the acid dissolved completely. The addition of bis(tributyltin) oxide (2.98 g, 5 mmol) gave an immediate precipitate. More ethanol was added to dissolve the solid, and slow evaporation of the filtered solution led to yellow blocks of (I). The solid-state 119Sn NMR spectrum consists of three signals (4:3:1 intensity ratio) at −55, −60 and −64 p.p.m. relative to tetramethyltin. A similar reaction with N-methylaniline, 2,6-pyridinedicarboxylic acid and bis(tributyltin) oxide gave (II) as long plates.
For (I), the 1,2- and 1,3-related carbon-carbon distances in the butyl chains and cyclohexyl rings were restrained by DFIX 1.54±0.01 and DFIX 2.52±0.02 Å; temperature factor restraints (SIMU 0.02) were imposed on the six butyl groups. Additionally, the temperature factors were restrained so that the ellipsoids would not be too elongated by an ISOR 0.02 command in SHELXL97 (Sheldrick, 1997). The crystal was measured to 2θ = 56.5°; however, as the refinement converged to R >> 7%, an OMIT −3 50 instruction was used to eliminate the high angle reflections. For (II), one of the butyl chains is disordered over two positions, and this was refined as two half-site occupancy chains sharing a common C/a atom; the distances were similarly DFIXed.
For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII (Johnson, 1976) for (I); ORTEP-II (Johnson, 1976) for (II). For both compounds, software used to prepare material for publication: SHELXL97.
(I) Dicyclohexylammonium 4-oxo-4
H-pyran-2,6-dicarboxylatotributylstannate
top
Crystal data top
(C12H24N)[Sn(C7H2O6)(C4H9)3] | F(000) = 2752 |
Mr = 654.43 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.1212 (3) Å | Cell parameters from 7059 reflections |
b = 18.0363 (2) Å | θ = 1.1–28.3° |
c = 21.8937 (1) Å | µ = 0.76 mm−1 |
β = 98.454 (1)° | T = 298 K |
V = 7078.0 (1) Å3 | Parallelepiped, colorless |
Z = 8 | 0.38 × 0.24 × 0.20 mm |
Data collection top
Siemens CCD area-detector diffractometer | 12367 independent reflections |
Radiation source: fine-focus sealed tube | 6929 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scan | θmax = 25.0°, θmin = 1.1° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −21→15 |
Tmin = 0.761, Tmax = 0.863 | k = −19→21 |
36773 measured reflections | l = −26→26 |
Refinement top
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0667P)2 + 9.8444P] where P = (Fo2 + 2Fc2)/3 |
12367 reflections | (Δ/σ)max < 0.001 |
703 parameters | Δρmax = 0.74 e Å−3 |
330 restraints | Δρmin = −0.43 e Å−3 |
Crystal data top
(C12H24N)[Sn(C7H2O6)(C4H9)3] | V = 7078.0 (1) Å3 |
Mr = 654.43 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.1212 (3) Å | µ = 0.76 mm−1 |
b = 18.0363 (2) Å | T = 298 K |
c = 21.8937 (1) Å | 0.38 × 0.24 × 0.20 mm |
β = 98.454 (1)° | |
Data collection top
Siemens CCD area-detector diffractometer | 12367 independent reflections |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | 6929 reflections with I > 2σ(I) |
Tmin = 0.761, Tmax = 0.863 | Rint = 0.055 |
36773 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 330 restraints |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.74 e Å−3 |
12367 reflections | Δρmin = −0.43 e Å−3 |
703 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1a | 0.38443 (3) | 0.24258 (3) | −0.01880 (2) | 0.0833 (2) | |
O1a | 0.3738 (3) | 0.1835 (3) | 0.0718 (2) | 0.091 (2) | |
O2a | 0.4280 (3) | 0.2729 (3) | 0.1329 (2) | 0.084 (1) | |
O3a | 0.3824 (4) | 0.1968 (3) | 0.3890 (2) | 0.111 (2) | |
O4a | 0.4461 (4) | 0.2755 (3) | 0.3372 (2) | 0.104 (2) | |
O5a | 0.3999 (2) | 0.2044 (2) | 0.2324 (2) | 0.061 (1) | |
O6a | 0.3131 (3) | −0.0031 (3) | 0.2297 (2) | 0.105 (2) | |
N1a | 0.4960 (3) | 0.3469 (3) | 0.2380 (2) | 0.068 (1) | |
C1a | 0.3274 (6) | 0.1500 (6) | −0.0637 (4) | 0.139 (4) | |
C2a | 0.2441 (7) | 0.1542 (8) | −0.0599 (7) | 0.212 (5) | |
C3a | 0.2025 (7) | 0.0856 (8) | −0.0853 (8) | 0.233 (6) | |
C4a | 0.1195 (7) | 0.1001 (9) | −0.0904 (8) | 0.254 (8) | |
C5a | 0.5030 (6) | 0.2388 (6) | 0.0000 (5) | 0.141 (4) | |
C6a | 0.5256 (8) | 0.1562 (7) | 0.0011 (8) | 0.233 (6) | |
C7a | 0.6077 (8) | 0.1408 (9) | 0.010 (1) | 0.301 (8) | |
C8a | 0.614 (1) | 0.059 (1) | −0.007 (1) | 0.33 (1) | |
C9a | 0.3191 (7) | 0.3291 (6) | 0.0063 (5) | 0.161 (4) | |
C10a | 0.324 (1) | 0.4106 (8) | −0.007 (1) | 0.312 (8) | |
C11a | 0.403 (1) | 0.436 (1) | 0.021 (1) | 0.34 (1) | |
C12a | 0.408 (2) | 0.512 (1) | −0.014 (2) | 0.53 (2) | |
C13a | 0.3950 (4) | 0.2137 (4) | 0.1231 (3) | 0.071 (2) | |
C14a | 0.3790 (3) | 0.1678 (4) | 0.1780 (2) | 0.055 (2) | |
C15a | 0.3483 (4) | 0.1013 (4) | 0.1748 (3) | 0.065 (2) | |
C16a | 0.3360 (4) | 0.0605 (4) | 0.2304 (3) | 0.074 (2) | |
C17a | 0.3549 (4) | 0.1038 (4) | 0.2862 (3) | 0.072 (2) | |
C18a | 0.3852 (4) | 0.1700 (4) | 0.2853 (2) | 0.064 (2) | |
C19a | 0.4082 (5) | 0.2209 (5) | 0.3417 (3) | 0.081 (2) | |
C20a | 0.4675 (4) | 0.4239 (4) | 0.2426 (3) | 0.081 (2) | |
C21a | 0.4933 (4) | 0.4564 (4) | 0.3065 (4) | 0.109 (3) | |
C22a | 0.4613 (5) | 0.5341 (5) | 0.3125 (5) | 0.147 (4) | |
C23a | 0.3763 (5) | 0.5325 (6) | 0.2983 (6) | 0.163 (5) | |
C24a | 0.3508 (5) | 0.5009 (5) | 0.2338 (5) | 0.158 (5) | |
C25a | 0.3823 (4) | 0.4225 (4) | 0.2285 (4) | 0.102 (3) | |
C26a | 0.5778 (4) | 0.3393 (4) | 0.2344 (3) | 0.081 (2) | |
C27a | 0.6010 (4) | 0.2601 (4) | 0.2505 (5) | 0.125 (3) | |
C28a | 0.6843 (5) | 0.2496 (7) | 0.2483 (6) | 0.165 (5) | |
C29a | 0.7005 (5) | 0.2689 (6) | 0.1840 (6) | 0.148 (5) | |
C30a | 0.6769 (4) | 0.3481 (6) | 0.1661 (5) | 0.133 (4) | |
C31a | 0.5945 (4) | 0.3611 (5) | 0.1709 (3) | 0.105 (3) | |
Sn1b | 0.88239 (4) | 0.27728 (3) | 0.45858 (2) | 0.1011 (3) | |
O1b | 0.8709 (4) | 0.2207 (3) | 0.3642 (2) | 0.113 (2) | |
O2b | 0.9337 (4) | 0.2965 (3) | 0.3101 (2) | 0.109 (2) | |
O3b | 0.8857 (3) | 0.1692 (3) | 0.0539 (2) | 0.106 (2) | |
O4b | 0.9351 (4) | 0.2662 (3) | 0.1076 (2) | 0.101 (2) | |
O5b | 0.9012 (2) | 0.2109 (2) | 0.2110 (2) | 0.068 (1) | |
O6b | 0.8210 (3) | 0.0027 (3) | 0.2234 (3) | 0.111 (2) | |
N1b | 0.9903 (3) | 0.3531 (3) | 0.2080 (2) | 0.071 (1) | |
C1b | 0.8083 (7) | 0.1914 (8) | 0.4868 (5) | 0.189 (5) | |
C2b | 0.7364 (9) | 0.201 (1) | 0.4416 (9) | 0.301 (8) | |
C3b | 0.687 (1) | 0.134 (1) | 0.447 (1) | 0.39 (1) | |
C4b | 0.617 (1) | 0.137 (2) | 0.398 (1) | 0.47 (2) | |
C5b | 0.9993 (6) | 0.2498 (6) | 0.4712 (5) | 0.133 (3) | |
C6b | 1.0086 (7) | 0.1642 (6) | 0.4733 (7) | 0.192 (5) | |
C7b | 1.0904 (8) | 0.1419 (9) | 0.4738 (9) | 0.256 (7) | |
C8b | 1.098 (1) | 0.0579 (9) | 0.493 (1) | 0.33 (1) | |
C9b | 0.8353 (6) | 0.3795 (6) | 0.4219 (4) | 0.151 (4) | |
C10b | 0.8924 (7) | 0.4417 (6) | 0.4278 (6) | 0.174 (4) | |
C11b | 0.8562 (7) | 0.5163 (6) | 0.4056 (7) | 0.202 (5) | |
C12b | 0.9200 (9) | 0.5724 (8) | 0.4079 (8) | 0.249 (8) | |
C13b | 0.8978 (5) | 0.2405 (5) | 0.3170 (3) | 0.087 (2) | |
C14b | 0.8822 (4) | 0.1849 (4) | 0.2653 (2) | 0.065 (2) | |
C15b | 0.8543 (4) | 0.1175 (4) | 0.2705 (3) | 0.073 (2) | |
C16b | 0.8415 (4) | 0.0668 (4) | 0.2189 (3) | 0.076 (2) | |
C17b | 0.8580 (4) | 0.0989 (4) | 0.1624 (3) | 0.073 (2) | |
C18b | 0.8863 (4) | 0.1665 (4) | 0.1600 (2) | 0.064 (2) | |
C19b | 0.9056 (5) | 0.2054 (4) | 0.1029 (3) | 0.082 (2) | |
C20b | 0.9556 (3) | 0.4269 (4) | 0.1938 (3) | 0.079 (2) | |
C21b | 0.9762 (5) | 0.4823 (4) | 0.2459 (4) | 0.127 (4) | |
C22b | 0.9406 (5) | 0.5584 (4) | 0.2278 (6) | 0.161 (5) | |
C23b | 0.8562 (5) | 0.5512 (5) | 0.2137 (5) | 0.141 (4) | |
C24b | 0.8342 (5) | 0.4945 (5) | 0.1631 (5) | 0.124 (3) | |
C25b | 0.8704 (4) | 0.4192 (4) | 0.1804 (4) | 0.100 (3) | |
C26b | 1.0735 (4) | 0.3487 (4) | 0.2144 (3) | 0.086 (2) | |
C27b | 1.1023 (4) | 0.3733 (5) | 0.1561 (4) | 0.117 (3) | |
C28b | 1.1876 (4) | 0.3627 (6) | 0.1608 (5) | 0.148 (4) | |
C29b | 1.2098 (6) | 0.2840 (7) | 0.1812 (7) | 0.198 (8) | |
C30b | 1.1831 (6) | 0.2621 (7) | 0.2417 (7) | 0.197 (8) | |
C31b | 1.0969 (5) | 0.2701 (4) | 0.2343 (6) | 0.149 (5) | |
H1a1 | 0.4704 | 0.3255 | 0.2042 | 0.102* | |
H1a2 | 0.4860 | 0.3211 | 0.2710 | 0.102* | |
H1a3 | 0.3349 | 0.1491 | −0.1066 | 0.209* | |
H1a4 | 0.3477 | 0.1046 | −0.0443 | 0.209* | |
H2a1 | 0.2372 | 0.1608 | −0.0171 | 0.318* | |
H2a2 | 0.2232 | 0.1972 | −0.0829 | 0.318* | |
H3a1 | 0.2162 | 0.0438 | −0.0581 | 0.350* | |
H3a2 | 0.2154 | 0.0738 | −0.1257 | 0.350* | |
H4a1 | 0.0926 | 0.0571 | −0.1073 | 0.382* | |
H4a2 | 0.1065 | 0.1418 | −0.1170 | 0.382* | |
H4a3 | 0.1069 | 0.1104 | −0.0502 | 0.382* | |
H5a1 | 0.5246 | 0.2650 | −0.0318 | 0.211* | |
H5a2 | 0.5205 | 0.2618 | 0.0395 | 0.211* | |
H6a1 | 0.5043 | 0.1319 | 0.0340 | 0.349* | |
H6a2 | 0.5035 | 0.1338 | −0.0375 | 0.349* | |
H7a1 | 0.6295 | 0.1492 | 0.0528 | 0.451* | |
H7a2 | 0.6327 | 0.1722 | −0.0163 | 0.451* | |
H8a1 | 0.6654 | 0.0464 | −0.0061 | 0.493* | |
H8a2 | 0.5877 | 0.0513 | −0.0481 | 0.493* | |
H8a3 | 0.5922 | 0.0289 | 0.0215 | 0.493* | |
H9a1 | 0.2682 | 0.3155 | −0.0100 | 0.242* | |
H9a2 | 0.3228 | 0.3257 | 0.0508 | 0.242* | |
H10a | 0.2871 | 0.4378 | 0.0114 | 0.468* | |
H10b | 0.3159 | 0.4193 | −0.0513 | 0.468* | |
H11a | 0.4410 | 0.4016 | 0.0117 | 0.512* | |
H11b | 0.4075 | 0.4436 | 0.0649 | 0.512* | |
H12a | 0.4547 | 0.5352 | 0.0004 | 0.793* | |
H12b | 0.3677 | 0.5431 | −0.0067 | 0.793* | |
H12c | 0.4046 | 0.5022 | −0.0577 | 0.793* | |
H15a | 0.3340 | 0.0798 | 0.1363 | 0.098* | |
H17a | 0.3453 | 0.0844 | 0.3236 | 0.108* | |
H20a | 0.4868 | 0.4548 | 0.2118 | 0.122* | |
H21a | 0.5474 | 0.4588 | 0.3137 | 0.163* | |
H21b | 0.4774 | 0.4242 | 0.3377 | 0.163* | |
H22a | 0.4764 | 0.5524 | 0.3541 | 0.220* | |
H22b | 0.4809 | 0.5674 | 0.2841 | 0.220* | |
H23a | 0.3569 | 0.5824 | 0.3007 | 0.244* | |
H23b | 0.3565 | 0.5023 | 0.3288 | 0.244* | |
H24a | 0.3678 | 0.5329 | 0.2031 | 0.237* | |
H24b | 0.2967 | 0.4992 | 0.2259 | 0.237* | |
H25a | 0.3626 | 0.3897 | 0.2573 | 0.153* | |
H25b | 0.3670 | 0.4036 | 0.1871 | 0.153* | |
H26a | 0.6055 | 0.3725 | 0.2651 | 0.121* | |
H27a | 0.5725 | 0.2265 | 0.2215 | 0.187* | |
H27b | 0.5903 | 0.2484 | 0.2916 | 0.187* | |
H28a | 0.7132 | 0.2815 | 0.2786 | 0.247* | |
H28b | 0.6985 | 0.1986 | 0.2581 | 0.247* | |
H29a | 0.6740 | 0.2347 | 0.1543 | 0.223* | |
H29b | 0.7535 | 0.2633 | 0.1826 | 0.223* | |
H30a | 0.6854 | 0.3577 | 0.1241 | 0.200* | |
H30b | 0.7072 | 0.3825 | 0.1931 | 0.200* | |
H31a | 0.5824 | 0.4130 | 0.1634 | 0.157* | |
H31b | 0.5637 | 0.3320 | 0.1397 | 0.157* | |
H1b1 | 0.9712 | 0.3215 | 0.1780 | 0.107* | |
H1b2 | 0.9764 | 0.3368 | 0.2435 | 0.107* | |
H1b3 | 0.8292 | 0.1424 | 0.4833 | 0.284* | |
H1b4 | 0.7997 | 0.1991 | 0.5290 | 0.284* | |
H2b1 | 0.7106 | 0.2457 | 0.4515 | 0.451* | |
H2b2 | 0.7476 | 0.2055 | 0.3998 | 0.451* | |
H3b1 | 0.6733 | 0.1316 | 0.4878 | 0.582* | |
H3b2 | 0.7153 | 0.0889 | 0.4407 | 0.582* | |
H4b1 | 0.5907 | 0.0905 | 0.3974 | 0.705* | |
H4b2 | 0.6305 | 0.1465 | 0.3582 | 0.705* | |
H4b3 | 0.5848 | 0.1761 | 0.4086 | 0.705* | |
H5b1 | 1.0222 | 0.2700 | 0.4374 | 0.200* | |
H5b2 | 1.0240 | 0.2713 | 0.5094 | 0.200* | |
H6b1 | 0.9912 | 0.1450 | 0.5100 | 0.288* | |
H6b2 | 0.9782 | 0.1425 | 0.4375 | 0.288* | |
H7b1 | 1.1227 | 0.1720 | 0.5031 | 0.384* | |
H7b2 | 1.1046 | 0.1490 | 0.4331 | 0.384* | |
H8b1 | 1.1488 | 0.0425 | 0.4945 | 0.497* | |
H8b2 | 1.0666 | 0.0284 | 0.4628 | 0.497* | |
H8b3 | 1.0825 | 0.0513 | 0.5326 | 0.497* | |
H9b1 | 0.8153 | 0.3727 | 0.3787 | 0.227* | |
H9b2 | 0.7944 | 0.3933 | 0.4436 | 0.227* | |
H10c | 0.9314 | 0.4297 | 0.4035 | 0.261* | |
H10d | 0.9151 | 0.4462 | 0.4706 | 0.261* | |
H11c | 0.8301 | 0.5118 | 0.3638 | 0.303* | |
H11d | 0.8210 | 0.5320 | 0.4323 | 0.303* | |
H12d | 0.9003 | 0.6198 | 0.3939 | 0.373* | |
H12e | 0.9549 | 0.5558 | 0.3818 | 0.373* | |
H12f | 0.9450 | 0.5767 | 0.4496 | 0.373* | |
H15b | 0.8426 | 0.1025 | 0.3086 | 0.109* | |
H17b | 0.8486 | 0.0713 | 0.1262 | 0.110* | |
H20b | 0.9731 | 0.4463 | 0.1567 | 0.118* | |
H21c | 1.0300 | 0.4875 | 0.2545 | 0.191* | |
H21d | 0.9587 | 0.4645 | 0.2831 | 0.191* | |
H22c | 0.9536 | 0.5932 | 0.2614 | 0.241* | |
H22d | 0.9598 | 0.5773 | 0.1918 | 0.241* | |
H23c | 0.8367 | 0.5362 | 0.2507 | 0.212* | |
H23d | 0.8347 | 0.5989 | 0.2008 | 0.212* | |
H24c | 0.8496 | 0.5119 | 0.1250 | 0.187* | |
H24d | 0.7804 | 0.4891 | 0.1562 | 0.187* | |
H25c | 0.8571 | 0.3845 | 0.1467 | 0.150* | |
H25d | 0.8519 | 0.3998 | 0.2165 | 0.150* | |
H26b | 1.0941 | 0.3824 | 0.2477 | 0.129* | |
H27c | 1.0902 | 0.4252 | 0.1485 | 0.176* | |
H27d | 1.0776 | 0.3449 | 0.1213 | 0.176* | |
H28c | 1.2030 | 0.3725 | 0.1210 | 0.221* | |
H28d | 1.2129 | 0.3978 | 0.1904 | 0.221* | |
H29c | 1.2637 | 0.2797 | 0.1862 | 0.296* | |
H29d | 1.1891 | 0.2497 | 0.1491 | 0.296* | |
H30c | 1.2062 | 0.2939 | 0.2749 | 0.296* | |
H30d | 1.1972 | 0.2113 | 0.2520 | 0.296* | |
H31c | 1.0739 | 0.2351 | 0.2037 | 0.223* | |
H31d | 1.0799 | 0.2589 | 0.2733 | 0.223* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1a | 0.1075 (4) | 0.1069 (4) | 0.0382 (2) | −0.0017 (3) | 0.0198 (2) | −0.0033 (2) |
O1a | 0.129 (4) | 0.110 (4) | 0.034 (2) | −0.027 (3) | 0.017 (2) | −0.008 (2) |
O2a | 0.112 (4) | 0.091 (3) | 0.049 (2) | −0.028 (3) | 0.012 (2) | 0.004 (2) |
O3a | 0.175 (5) | 0.123 (4) | 0.041 (3) | −0.031 (4) | 0.040 (3) | −0.008 (2) |
O4a | 0.147 (5) | 0.117 (4) | 0.050 (3) | −0.038 (4) | 0.020 (3) | −0.011 (3) |
O5a | 0.076 (3) | 0.075 (3) | 0.034 (2) | 0.000 (2) | 0.015 (2) | 0.001 (2) |
O6a | 0.154 (5) | 0.070 (3) | 0.098 (4) | −0.015 (3) | 0.039 (3) | 0.005 (3) |
N1a | 0.066 (4) | 0.076 (4) | 0.063 (3) | −0.010 (3) | 0.014 (3) | −0.008 (2) |
C1a | 0.160 (8) | 0.178 (8) | 0.082 (5) | −0.043 (8) | 0.023 (6) | −0.029 (6) |
C2a | 0.23 (1) | 0.22 (1) | 0.182 (9) | −0.04 (1) | 0.021 (9) | −0.085 (8) |
C3a | 0.23 (1) | 0.24 (1) | 0.22 (1) | −0.03 (1) | 0.02 (1) | −0.09 (1) |
C4a | 0.22 (1) | 0.27 (1) | 0.27 (1) | 0.03 (1) | 0.02 (1) | −0.10 (1) |
C5a | 0.145 (8) | 0.177 (9) | 0.105 (7) | −0.009 (7) | 0.037 (6) | 0.007 (6) |
C6a | 0.19 (1) | 0.26 (1) | 0.25 (1) | 0.02 (1) | 0.05 (1) | 0.07 (1) |
C7a | 0.30 (1) | 0.30 (1) | 0.31 (1) | −0.00 (1) | 0.07 (1) | 0.04 (1) |
C8a | 0.34 (2) | 0.30 (2) | 0.35 (2) | 0.01 (2) | 0.05 (2) | 0.00 (2) |
C9a | 0.22 (1) | 0.172 (9) | 0.100 (6) | 0.050 (9) | 0.053 (7) | 0.021 (6) |
C10a | 0.33 (1) | 0.31 (1) | 0.30 (1) | 0.02 (1) | 0.08 (1) | −0.01 (1) |
C11a | 0.33 (2) | 0.33 (2) | 0.36 (2) | 0.00 (1) | 0.06 (1) | 0.01 (1) |
C12a | 0.52 (2) | 0.52 (2) | 0.55 (2) | 0.03 (2) | 0.09 (2) | 0.00 (2) |
C13a | 0.082 (5) | 0.090 (5) | 0.044 (4) | 0.000 (4) | 0.020 (3) | 0.000 (3) |
C14a | 0.059 (4) | 0.071 (4) | 0.036 (3) | 0.007 (3) | 0.008 (3) | 0.001 (2) |
C15a | 0.074 (4) | 0.072 (4) | 0.051 (3) | 0.002 (4) | 0.016 (3) | −0.003 (3) |
C16a | 0.095 (5) | 0.066 (5) | 0.066 (4) | 0.004 (4) | 0.025 (4) | 0.004 (3) |
C17a | 0.095 (5) | 0.072 (5) | 0.053 (4) | −0.002 (4) | 0.023 (3) | 0.009 (3) |
C18a | 0.069 (4) | 0.087 (5) | 0.039 (3) | 0.011 (4) | 0.017 (3) | 0.005 (3) |
C19a | 0.105 (6) | 0.100 (6) | 0.040 (4) | 0.003 (5) | 0.020 (4) | −0.004 (3) |
C20a | 0.083 (6) | 0.072 (5) | 0.092 (5) | −0.005 (4) | 0.030 (4) | −0.006 (4) |
C21a | 0.095 (6) | 0.109 (7) | 0.128 (7) | −0.020 (5) | 0.033 (5) | −0.047 (5) |
C22a | 0.114 (8) | 0.112 (8) | 0.22 (1) | −0.010 (6) | 0.046 (8) | −0.070 (8) |
C23a | 0.13 (1) | 0.105 (8) | 0.27 (2) | −0.002 (7) | 0.08 (1) | −0.064 (9) |
C24a | 0.113 (8) | 0.13 (1) | 0.24 (2) | 0.034 (7) | 0.069 (9) | −0.005 (9) |
C25a | 0.081 (6) | 0.104 (6) | 0.123 (7) | 0.006 (5) | 0.024 (5) | −0.006 (5) |
C26a | 0.069 (5) | 0.086 (5) | 0.086 (5) | −0.001 (4) | 0.008 (4) | −0.015 (4) |
C27a | 0.087 (7) | 0.113 (7) | 0.17 (1) | 0.021 (6) | 0.019 (6) | 0.024 (6) |
C28a | 0.115 (9) | 0.18 (1) | 0.20 (1) | 0.060 (8) | 0.024 (9) | 0.00 (1) |
C29a | 0.085 (7) | 0.14 (1) | 0.22 (1) | 0.012 (7) | 0.040 (8) | −0.067 (9) |
C30a | 0.090 (7) | 0.150 (9) | 0.17 (1) | −0.008 (7) | 0.065 (6) | −0.028 (8) |
C31a | 0.078 (6) | 0.138 (7) | 0.107 (6) | −0.001 (5) | 0.044 (5) | −0.004 (5) |
Sn1b | 0.1472 (6) | 0.1153 (5) | 0.0449 (3) | −0.0084 (4) | 0.0284 (3) | 0.0004 (2) |
O1b | 0.157 (5) | 0.143 (5) | 0.044 (3) | −0.033 (4) | 0.032 (3) | −0.011 (3) |
O2b | 0.165 (6) | 0.112 (4) | 0.054 (3) | −0.031 (4) | 0.028 (3) | −0.010 (3) |
O3b | 0.178 (6) | 0.098 (4) | 0.046 (3) | −0.020 (4) | 0.026 (3) | −0.007 (2) |
O4b | 0.170 (6) | 0.086 (4) | 0.051 (3) | −0.027 (4) | 0.033 (3) | 0.000 (2) |
O5b | 0.089 (3) | 0.077 (3) | 0.040 (2) | −0.006 (2) | 0.016 (2) | 0.000 (2) |
O6b | 0.143 (5) | 0.082 (4) | 0.120 (4) | −0.016 (4) | 0.059 (4) | 0.007 (3) |
N1b | 0.077 (4) | 0.071 (4) | 0.068 (3) | −0.006 (3) | 0.022 (3) | −0.003 (3) |
C1b | 0.20 (1) | 0.27 (1) | 0.099 (7) | −0.09 (1) | 0.024 (7) | −0.003 (8) |
C2b | 0.32 (1) | 0.33 (1) | 0.27 (1) | −0.09 (1) | 0.10 (1) | 0.04 (1) |
C3b | 0.40 (2) | 0.39 (2) | 0.37 (2) | −0.05 (1) | 0.04 (1) | 0.02 (1) |
C4b | 0.48 (2) | 0.47 (2) | 0.46 (2) | 0.03 (2) | 0.05 (2) | 0.01 (2) |
C5b | 0.141 (7) | 0.169 (8) | 0.098 (6) | −0.036 (7) | 0.044 (6) | −0.009 (6) |
C6b | 0.178 (9) | 0.22 (1) | 0.186 (9) | 0.037 (9) | 0.037 (8) | −0.024 (9) |
C7b | 0.25 (1) | 0.26 (1) | 0.25 (1) | 0.04 (1) | 0.03 (1) | −0.04 (1) |
C8b | 0.34 (2) | 0.33 (2) | 0.32 (2) | 0.06 (2) | 0.06 (1) | −0.03 (2) |
C9b | 0.19 (1) | 0.176 (9) | 0.082 (6) | 0.006 (8) | 0.010 (6) | 0.005 (6) |
C10b | 0.22 (1) | 0.164 (9) | 0.129 (7) | 0.004 (8) | 0.000 (7) | 0.033 (7) |
C11b | 0.24 (1) | 0.20 (1) | 0.149 (9) | 0.01 (1) | −0.004 (9) | 0.018 (9) |
C12b | 0.30 (2) | 0.21 (1) | 0.22 (1) | −0.04 (1) | 0.01 (1) | −0.01 (1) |
C13b | 0.114 (6) | 0.101 (6) | 0.047 (4) | 0.000 (5) | 0.016 (4) | −0.002 (4) |
C14b | 0.072 (4) | 0.086 (5) | 0.038 (3) | 0.003 (4) | 0.013 (3) | 0.011 (3) |
C15b | 0.073 (5) | 0.094 (5) | 0.055 (4) | 0.008 (4) | 0.022 (3) | 0.015 (3) |
C16b | 0.079 (5) | 0.077 (5) | 0.079 (5) | −0.001 (4) | 0.030 (4) | 0.009 (4) |
C17b | 0.091 (5) | 0.073 (5) | 0.060 (4) | −0.004 (4) | 0.025 (3) | −0.005 (3) |
C18b | 0.074 (4) | 0.077 (5) | 0.041 (3) | 0.002 (4) | 0.008 (3) | −0.001 (3) |
C19b | 0.122 (6) | 0.083 (5) | 0.043 (4) | 0.005 (5) | 0.025 (4) | 0.002 (3) |
C20b | 0.073 (5) | 0.077 (5) | 0.089 (5) | −0.008 (4) | 0.022 (4) | 0.006 (4) |
C21b | 0.099 (7) | 0.099 (7) | 0.18 (1) | −0.004 (6) | 0.000 (6) | −0.046 (6) |
C22b | 0.095 (8) | 0.089 (7) | 0.30 (2) | 0.010 (6) | 0.019 (8) | −0.046 (8) |
C23b | 0.107 (8) | 0.105 (7) | 0.22 (1) | 0.006 (6) | 0.033 (8) | −0.017 (8) |
C24b | 0.084 (6) | 0.132 (8) | 0.156 (9) | 0.011 (6) | 0.014 (6) | 0.025 (7) |
C25b | 0.078 (6) | 0.094 (6) | 0.129 (7) | −0.004 (5) | 0.020 (5) | 0.000 (5) |
C26b | 0.079 (5) | 0.082 (5) | 0.095 (5) | 0.005 (4) | 0.009 (4) | −0.008 (4) |
C27b | 0.089 (6) | 0.152 (8) | 0.119 (7) | 0.003 (6) | 0.041 (5) | −0.011 (6) |
C28b | 0.084 (7) | 0.19 (1) | 0.18 (1) | −0.004 (7) | 0.046 (7) | −0.032 (9) |
C29b | 0.109 (9) | 0.13 (1) | 0.35 (2) | 0.039 (9) | 0.02 (1) | −0.07 (1) |
C30b | 0.12 (1) | 0.14 (1) | 0.33 (2) | 0.038 (9) | 0.01 (1) | 0.06 (1) |
C31b | 0.115 (9) | 0.087 (7) | 0.24 (1) | 0.016 (6) | 0.007 (8) | 0.023 (7) |
Geometric parameters (Å, º) top
Sn1a—C1a | 2.127 (9) | C6a—H6a1 | 0.9700 |
Sn1a—C5a | 2.13 (1) | C6a—H6a2 | 0.9700 |
Sn1a—C9a | 2.08 (1) | C7a—H7a1 | 0.9700 |
Sn1a—O1a | 2.285 (4) | C7a—H7a2 | 0.9700 |
Sn1a—O3ai | 2.292 (4) | C8a—H8a1 | 0.9600 |
O1a—C13a | 1.256 (8) | C8a—H8a2 | 0.9600 |
O2a—C13a | 1.226 (8) | C8a—H8a3 | 0.9600 |
O3a—C19a | 1.274 (8) | C9a—H9a1 | 0.9700 |
O4a—C19a | 1.213 (8) | C9a—H9a2 | 0.9700 |
O5a—C14a | 1.365 (6) | C10a—H10a | 0.9700 |
O5a—C18a | 1.376 (7) | C10a—H10b | 0.9700 |
O6a—C16a | 1.220 (8) | C11a—H11a | 0.9700 |
N1a—C20a | 1.490 (8) | C11a—H11b | 0.9700 |
N1a—C26a | 1.501 (8) | C12a—H12a | 0.9600 |
C1a—C2a | 1.525 (9) | C12a—H12b | 0.9600 |
C2a—C3a | 1.513 (9) | C12a—H12c | 0.9600 |
C3a—C4a | 1.514 (9) | C15a—H15a | 0.9300 |
C5a—C6a | 1.544 (9) | C17a—H17a | 0.9300 |
C6a—C7a | 1.497 (9) | C20a—H20a | 0.9800 |
C7a—C8a | 1.53 (1) | C21a—H21a | 0.9700 |
C9a—C10a | 1.50 (1) | C21a—H21b | 0.9700 |
C10a—C11a | 1.54 (1) | C22a—H22a | 0.9700 |
C11a—C12a | 1.56 (1) | C22a—H22b | 0.9700 |
C13a—C14a | 1.523 (8) | C23a—H23a | 0.9700 |
C14a—C15a | 1.319 (8) | C23a—H23b | 0.9700 |
C15a—C16a | 1.467 (9) | C24a—H24a | 0.9700 |
C16a—C17a | 1.449 (9) | C24a—H24b | 0.9700 |
C17a—C18a | 1.315 (9) | C25a—H25a | 0.9700 |
C18a—C19a | 1.544 (9) | C25a—H25b | 0.9700 |
C20a—C21a | 1.525 (7) | C26a—H26a | 0.9800 |
C20a—C25a | 1.530 (7) | C27a—H27a | 0.9700 |
C21a—C22a | 1.529 (8) | C27a—H27b | 0.9700 |
C22a—C23a | 1.527 (8) | C28a—H28a | 0.9700 |
C23a—C24a | 1.530 (9) | C28a—H28b | 0.9700 |
C24a—C25a | 1.536 (8) | C29a—H29a | 0.9700 |
C26a—C27a | 1.516 (7) | C29a—H29b | 0.9700 |
C26a—C31a | 1.519 (7) | C30a—H30a | 0.9700 |
C27a—C28a | 1.530 (8) | C30a—H30b | 0.9700 |
C28a—C29a | 1.521 (9) | C31a—H31a | 0.9700 |
C29a—C30a | 1.527 (8) | C31a—H31b | 0.9700 |
C30a—C31a | 1.530 (7) | N1b—H1b1 | 0.9000 |
Sn1b—C1b | 2.20 (1) | N1b—H1b2 | 0.9000 |
Sn1b—C5b | 2.15 (1) | C1b—H1b3 | 0.9700 |
Sn1b—C9b | 2.14 (1) | C1b—H1b4 | 0.9700 |
Sn1b—O1b | 2.286 (5) | C2b—H2b1 | 0.9700 |
Sn1b—O3bii | 2.292 (5) | C2b—H2b2 | 0.9700 |
O1b—C13b | 1.258 (9) | C3b—H3b1 | 0.9700 |
O2b—C13b | 1.223 (9) | C3b—H3b2 | 0.9700 |
O3b—C19b | 1.262 (8) | C4b—H4b1 | 0.9600 |
O4b—C19b | 1.218 (8) | C4b—H4b2 | 0.9600 |
O5b—C18b | 1.367 (7) | C4b—H4b3 | 0.9600 |
O5b—C14b | 1.369 (7) | C5b—H5b1 | 0.9700 |
O6b—C16b | 1.222 (8) | C5b—H5b2 | 0.9700 |
N1b—C20b | 1.486 (8) | C6b—H6b1 | 0.9700 |
N1b—C26b | 1.495 (8) | C6b—H6b2 | 0.9700 |
C1b—C2b | 1.53 (1) | C7b—H7b1 | 0.9700 |
C2b—C3b | 1.52 (1) | C7b—H7b2 | 0.9700 |
C3b—C4b | 1.54 (1) | C8b—H8b1 | 0.9600 |
C5b—C6b | 1.552 (9) | C8b—H8b2 | 0.9600 |
C6b—C7b | 1.534 (9) | C8b—H8b3 | 0.9600 |
C7b—C8b | 1.57 (1) | C9b—H9b1 | 0.9700 |
C9b—C10b | 1.519 (9) | C9b—H9b2 | 0.9700 |
C10b—C11b | 1.544 (9) | C10b—H10c | 0.9700 |
C11b—C12b | 1.531 (9) | C10b—H10d | 0.9700 |
C13b—C14b | 1.51 (1) | C11b—H11c | 0.9700 |
C14b—C15b | 1.327 (9) | C11b—H11d | 0.9700 |
C15b—C16b | 1.445 (9) | C12b—H12d | 0.9600 |
C18b—C19b | 1.520 (9) | C12b—H12e | 0.9600 |
C20b—C21b | 1.521 (7) | C12b—H12f | 0.9600 |
C20b—C25b | 1.534 (7) | C15b—H15b | 0.9300 |
C21b—C22b | 1.542 (8) | C17b—H17b | 0.9300 |
C22b—C23b | 1.519 (8) | C20b—H20b | 0.9800 |
C23b—C24b | 1.516 (8) | C21b—H21c | 0.9700 |
C24b—C25b | 1.532 (8) | C21b—H21d | 0.9700 |
C26b—C27b | 1.516 (7) | C22b—H22c | 0.9700 |
C26b—C31b | 1.524 (7) | C22b—H22d | 0.9700 |
C27b—C28b | 1.545 (8) | C23b—H23c | 0.9700 |
C28b—C29b | 1.524 (9) | C23b—H23d | 0.9700 |
C29b—C30b | 1.527 (9) | C24b—H24c | 0.9700 |
C30b—C31b | 1.552 (9) | C24b—H24d | 0.9700 |
N1a—H1a1 | 0.9000 | C25b—H25c | 0.9700 |
N1a—H1a2 | 0.9000 | C25b—H25d | 0.9700 |
C1a—H1a3 | 0.9700 | C26b—H26b | 0.9800 |
C1a—H1a4 | 0.9700 | C27b—H27c | 0.9700 |
C2a—H2a1 | 0.9700 | C27b—H27d | 0.9700 |
C2a—H2a2 | 0.9700 | C28b—H28c | 0.9700 |
C3a—H3a1 | 0.9700 | C28b—H28d | 0.9700 |
C3a—H3a2 | 0.9700 | C29b—H29c | 0.9700 |
C4a—H4a1 | 0.9600 | C29b—H29d | 0.9700 |
C4a—H4a2 | 0.9600 | C30b—H30c | 0.9700 |
C4a—H4a3 | 0.9600 | C30b—H30d | 0.9700 |
C5a—H5a1 | 0.9700 | C31b—H31c | 0.9700 |
C5a—H5a2 | 0.9700 | C31b—H31d | 0.9700 |
| | | |
C1a—Sn1a—C5a | 118.2 (4) | N1a—C20a—H20a | 108.7 |
C1a—Sn1a—C9a | 117.0 (5) | C21a—C20a—H20a | 108.7 |
C1a—Sn1a—O1a | 86.5 (3) | C25a—C20a—H20a | 108.7 |
C1a—Sn1a—O3ai | 91.4 (3) | C20a—C21a—H21a | 109.4 |
C5a—Sn1a—C9a | 124.8 (5) | C22a—C21a—H21a | 109.4 |
C5a—Sn1a—O1a | 91.6 (3) | C20a—C21a—H21b | 109.4 |
C5a—Sn1a—O3ai | 94.0 (3) | C22a—C21a—H21b | 109.4 |
C9a—Sn1a—O1a | 89.8 (3) | H21a—C21a—H21b | 108.0 |
C9a—Sn1a—O3ai | 86.5 (3) | C23a—C22a—H22a | 109.6 |
O1a—Sn1a—O3ai | 174.3 (2) | C21a—C22a—H22a | 109.6 |
C13a—O1a—Sn1a | 121.3 (5) | C23a—C22a—H22b | 109.6 |
C19a—O3a—Sn1aii | 126.4 (5) | C21a—C22a—H22b | 109.6 |
C14a—O5a—C18a | 117.0 (5) | H22a—C22a—H22b | 108.1 |
C20a—N1a—C26a | 116.3 (5) | C22a—C23a—H23a | 109.5 |
C2a—C1a—Sn1a | 110.7 (7) | C24a—C23a—H23a | 109.5 |
C3a—C2a—C1a | 113 (1) | C22a—C23a—H23b | 109.5 |
C2a—C3a—C4a | 109 (1) | C24a—C23a—H23b | 109.5 |
C6a—C5a—Sn1a | 107.0 (8) | H23a—C23a—H23b | 108.1 |
C7a—C6a—C5a | 116 (1) | C23a—C24a—H24a | 109.6 |
C6a—C7a—C8a | 105 (1) | C25a—C24a—H24a | 109.6 |
C10a—C9a—Sn1a | 129 (1) | C23a—C24a—H24b | 109.6 |
C9a—C10a—C11a | 107 (1) | C25a—C24a—H24b | 109.6 |
C10a—C11a—C12a | 101 (1) | H24a—C24a—H24b | 108.1 |
O2a—C13a—O1a | 127.7 (6) | C20a—C25a—H25a | 109.6 |
O2a—C13a—C14a | 118.7 (6) | C24a—C25a—H25a | 109.6 |
O1a—C13a—C14a | 113.6 (6) | C20a—C25a—H25b | 109.6 |
C15a—C14a—O5a | 123.2 (5) | C24a—C25a—H25b | 109.6 |
C15a—C14a—C13a | 125.5 (5) | H25a—C25a—H25b | 108.1 |
O5a—C14a—C13a | 111.3 (5) | N1a—C26a—H26a | 108.6 |
C14a—C15a—C16a | 121.7 (6) | C27a—C26a—H26a | 108.6 |
O6a—C16a—C17a | 123.7 (6) | C31a—C26a—H26a | 108.6 |
O6a—C16a—C15a | 123.6 (6) | C26a—C27a—H27a | 109.5 |
C17a—C16a—C15a | 112.6 (6) | C28a—C27a—H27a | 109.5 |
C18a—C17a—C16a | 121.6 (6) | C26a—C27a—H27b | 109.5 |
C17a—C18a—O5a | 123.7 (5) | C28a—C27a—H27b | 109.5 |
C17a—C18a—C19a | 126.3 (6) | H27a—C27a—H27b | 108.1 |
O5a—C18a—C19a | 110.0 (6) | C29a—C28a—H28a | 109.9 |
O4a—C19a—O3a | 128.5 (7) | C27a—C28a—H28a | 109.9 |
O4a—C19a—C18a | 120.5 (6) | C29a—C28a—H28b | 109.9 |
O3a—C19a—C18a | 111.0 (7) | C27a—C28a—H28b | 109.9 |
N1a—C20a—C21a | 111.0 (6) | H28a—C28a—H28b | 108.3 |
N1a—C20a—C25a | 108.7 (5) | C28a—C29a—H29a | 109.3 |
C21a—C20a—C25a | 110.8 (6) | C30a—C29a—H29a | 109.3 |
C20a—C21a—C22a | 111.2 (7) | C28a—C29a—H29b | 109.3 |
C23a—C22a—C21a | 110.5 (7) | C30a—C29a—H29b | 109.3 |
C22a—C23a—C24a | 110.7 (8) | H29a—C29a—H29b | 108.0 |
C23a—C24a—C25a | 110.4 (7) | C29a—C30a—H30a | 109.3 |
C20a—C25a—C24a | 110.2 (6) | C31a—C30a—H30a | 109.3 |
N1a—C26a—C27a | 108.4 (6) | C29a—C30a—H30b | 109.3 |
N1a—C26a—C31a | 110.8 (5) | C31a—C30a—H30b | 109.3 |
C27a—C26a—C31a | 111.7 (6) | H30a—C30a—H30b | 108.0 |
C26a—C27a—C28a | 110.5 (7) | C26a—C31a—H31a | 109.5 |
C29a—C28a—C27a | 109.1 (8) | C30a—C31a—H31a | 109.5 |
C28a—C29a—C30a | 111.4 (8) | C26a—C31a—H31b | 109.5 |
C29a—C30a—C31a | 111.4 (7) | C30a—C31a—H31b | 109.5 |
C26a—C31a—C30a | 110.5 (6) | H31a—C31a—H31b | 108.1 |
C1b—Sn1b—C5b | 115.6 (5) | C20b—N1b—H1b1 | 108.0 |
C1b—Sn1b—C9b | 119.1 (5) | C26b—N1b—H1b1 | 108.0 |
C1b—Sn1b—O1b | 87.8 (4) | C20b—N1b—H1b2 | 108.0 |
C1b—Sn1b—O3bii | 88.6 (4) | C26b—N1b—H1b2 | 108.0 |
C5b—Sn1b—C9b | 125.3 (4) | H1b1—N1b—H1b2 | 107.2 |
C5b—Sn1b—O1b | 88.3 (3) | C2b—C1b—H1b3 | 111.0 |
C5b—Sn1b—O3bii | 94.9 (3) | Sn1b—C1b—H1b3 | 111.0 |
C9b—Sn1b—O1b | 93.8 (3) | C2b—C1b—H1b4 | 111.0 |
C9b—Sn1b—O3bii | 86.2 (3) | Sn1b—C1b—H1b4 | 111.0 |
O1b—Sn1b—O3bii | 176.0 (2) | H1b3—C1b—H1b4 | 109.0 |
C13b—O1b—Sn1b | 128.4 (5) | C3b—C2b—H2b1 | 110.1 |
C19b—O3b—Sn1bi | 121.4 (5) | C1b—C2b—H2b1 | 110.1 |
C18b—O5b—C14b | 117.6 (5) | C3b—C2b—H2b2 | 110.1 |
C20b—N1b—C26b | 117.3 (5) | C1b—C2b—H2b2 | 110.1 |
C2b—C1b—Sn1b | 103.7 (9) | H2b1—C2b—H2b2 | 108.4 |
C3b—C2b—C1b | 108 (1) | C2b—C3b—H3b1 | 109.5 |
C2b—C3b—C4b | 111 (1) | C4b—C3b—H3b1 | 109.5 |
C6b—C5b—Sn1b | 109.4 (7) | C2b—C3b—H3b2 | 109.5 |
C7b—C6b—C5b | 111 (1) | C4b—C3b—H3b2 | 109.5 |
C6b—C7b—C8b | 108 (1) | H3b1—C3b—H3b2 | 108.1 |
C10b—C9b—Sn1b | 112.1 (7) | C3b—C4b—H4b1 | 109.5 |
C9b—C10b—C11b | 111.4 (9) | C3b—C4b—H4b2 | 109.5 |
C12b—C11b—C10b | 106 (1) | H4b1—C4b—H4b2 | 109.5 |
O2b—C13b—O1b | 127.9 (7) | C3b—C4b—H4b3 | 109.5 |
O2b—C13b—C14b | 120.1 (7) | H4b1—C4b—H4b3 | 109.5 |
O1b—C13b—C14b | 112.0 (8) | H4b2—C4b—H4b3 | 109.5 |
C15b—C14b—O5b | 122.4 (6) | C6b—C5b—H5b1 | 109.8 |
C15b—C14b—C13b | 125.2 (6) | Sn1b—C5b—H5b1 | 109.8 |
O5b—C14b—C13b | 112.4 (6) | C6b—C5b—H5b2 | 109.8 |
C14b—C15b—C16b | 122.1 (6) | Sn1b—C5b—H5b2 | 109.8 |
O6b—C16b—C17b | 123.6 (7) | H5b1—C5b—H5b2 | 108.2 |
O6b—C16b—C15b | 123.5 (7) | C7b—C6b—H6b1 | 109.4 |
C17b—C16b—C15b | 112.9 (6) | C5b—C6b—H6b1 | 109.4 |
C18b—C17b—C16b | 122.2 (6) | C7b—C6b—H6b2 | 109.4 |
C17b—C18b—O5b | 122.6 (5) | C5b—C6b—H6b2 | 109.4 |
C17b—C18b—C19b | 126.4 (6) | H6b1—C6b—H6b2 | 108.0 |
O5b—C18b—C19b | 111.1 (6) | C6b—C7b—H7b1 | 110.2 |
O4b—C19b—O3b | 127.3 (6) | C8b—C7b—H7b1 | 110.2 |
O4b—C19b—C18b | 119.8 (6) | C6b—C7b—H7b2 | 110.2 |
O3b—C19b—C18b | 112.9 (7) | C8b—C7b—H7b2 | 110.2 |
N1b—C20b—C21b | 112.5 (6) | H7b1—C7b—H7b2 | 108.5 |
N1b—C20b—C25b | 110.0 (5) | C7b—C8b—H8b1 | 109.5 |
C21b—C20b—C25b | 109.5 (6) | C7b—C8b—H8b2 | 109.5 |
C20b—C21b—C22b | 110.1 (7) | H8b1—C8b—H8b2 | 109.5 |
C23b—C22b—C21b | 110.3 (7) | C7b—C8b—H8b3 | 109.5 |
C24b—C23b—C22b | 110.8 (7) | H8b1—C8b—H8b3 | 109.5 |
C23b—C24b—C25b | 111.1 (7) | H8b2—C8b—H8b3 | 109.5 |
C24b—C25b—C20b | 110.4 (6) | C10b—C9b—H9b1 | 109.2 |
N1b—C26b—C27b | 111.9 (6) | Sn1b—C9b—H9b1 | 109.2 |
N1b—C26b—C31b | 108.1 (6) | C10b—C9b—H9b2 | 109.2 |
C27b—C26b—C31b | 113.4 (7) | Sn1b—C9b—H9b2 | 109.2 |
C26b—C27b—C28b | 111.8 (7) | H9b1—C9b—H9b2 | 107.9 |
C29b—C28b—C27b | 110.7 (7) | C9b—C10b—H10c | 109.3 |
C28b—C29b—C30b | 113.0 (9) | C11b—C10b—H10c | 109.3 |
C29b—C30b—C31b | 109.1 (9) | C9b—C10b—H10d | 109.3 |
C26b—C31b—C30b | 110.5 (7) | C11b—C10b—H10d | 109.3 |
C20a—N1a—H1a1 | 108.2 | H10c—C10b—H10d | 108.0 |
C26a—N1a—H1a1 | 108.2 | C12b—C11b—H11c | 110.5 |
C20a—N1a—H1a2 | 108.2 | C10b—C11b—H11c | 110.5 |
C26a—N1a—H1a2 | 108.2 | C12b—C11b—H11d | 110.5 |
H1a1—N1a—H1a2 | 107.4 | C10b—C11b—H11d | 110.5 |
C2a—C1a—H1a3 | 109.5 | H11c—C11b—H11d | 108.6 |
Sn1a—C1a—H1a3 | 109.5 | C11b—C12b—H12d | 109.5 |
C2a—C1a—H1a4 | 109.5 | C11b—C12b—H12e | 109.5 |
Sn1a—C1a—H1a4 | 109.5 | H12d—C12b—H12e | 109.5 |
H1a3—C1a—H1a4 | 108.1 | C11b—C12b—H12f | 109.5 |
C3a—C2a—H2a1 | 109.1 | H12d—C12b—H12f | 109.5 |
C1a—C2a—H2a1 | 109.1 | H12e—C12b—H12f | 109.5 |
C3a—C2a—H2a2 | 109.1 | C14b—C15b—H15b | 118.9 |
C1a—C2a—H2a2 | 109.1 | C16b—C15b—H15b | 118.9 |
H2a1—C2a—H2a2 | 107.8 | C18b—C17b—H17b | 118.9 |
C2a—C3a—H3a1 | 109.9 | C16b—C17b—H17b | 118.9 |
C4a—C3a—H3a1 | 109.9 | N1b—C20b—H20b | 108.3 |
C2a—C3a—H3a2 | 109.9 | C21b—C20b—H20b | 108.3 |
C4a—C3a—H3a2 | 109.9 | C25b—C20b—H20b | 108.3 |
H3a1—C3a—H3a2 | 108.3 | C20b—C21b—H21c | 109.6 |
C3a—C4a—H4a1 | 109.5 | C22b—C21b—H21c | 109.6 |
C3a—C4a—H4a2 | 109.5 | C20b—C21b—H21d | 109.6 |
H4a1—C4a—H4a2 | 109.5 | C22b—C21b—H21d | 109.6 |
C3a—C4a—H4a3 | 109.5 | H21c—C21b—H21d | 108.1 |
H4a1—C4a—H4a3 | 109.5 | C23b—C22b—H22c | 109.6 |
H4a2—C4a—H4a3 | 109.5 | C21b—C22b—H22c | 109.6 |
C6a—C5a—H5a1 | 110.3 | C23b—C22b—H22d | 109.6 |
Sn1a—C5a—H5a1 | 110.3 | C21b—C22b—H22d | 109.6 |
C6a—C5a—H5a2 | 110.3 | H22c—C22b—H22d | 108.1 |
Sn1a—C5a—H5a2 | 110.3 | C24b—C23b—H23c | 109.5 |
H5a1—C5a—H5a2 | 108.6 | C22b—C23b—H23c | 109.5 |
C7a—C6a—H6a1 | 108.3 | C24b—C23b—H23d | 109.5 |
C5a—C6a—H6a1 | 108.3 | C22b—C23b—H23d | 109.5 |
C7a—C6a—H6a2 | 108.3 | H23c—C23b—H23d | 108.1 |
C5a—C6a—H6a2 | 108.3 | C23b—C24b—H24c | 109.4 |
H6a1—C6a—H6a2 | 107.4 | C25b—C24b—H24c | 109.4 |
C6a—C7a—H7a1 | 110.8 | C23b—C24b—H24d | 109.4 |
C8a—C7a—H7a1 | 110.8 | C25b—C24b—H24d | 109.4 |
C6a—C7a—H7a2 | 110.8 | H24c—C24b—H24d | 108.0 |
C8a—C7a—H7a2 | 110.8 | C24b—C25b—H25c | 109.6 |
H7a1—C7a—H7a2 | 108.9 | C20b—C25b—H25c | 109.6 |
C7a—C8a—H8a1 | 109.5 | C24b—C25b—H25d | 109.6 |
C7a—C8a—H8a2 | 109.5 | C20b—C25b—H25d | 109.6 |
H8a1—C8a—H8a2 | 109.5 | H25c—C25b—H25d | 108.1 |
C7a—C8a—H8a3 | 109.5 | N1b—C26b—H26b | 107.7 |
H8a1—C8a—H8a3 | 109.5 | C27b—C26b—H26b | 107.7 |
H8a2—C8a—H8a3 | 109.5 | C31b—C26b—H26b | 107.7 |
C10a—C9a—H9a1 | 105.1 | C26b—C27b—H27c | 109.3 |
Sn1a—C9a—H9a1 | 105.1 | C28b—C27b—H27c | 109.3 |
C10a—C9a—H9a2 | 105.1 | C26b—C27b—H27d | 109.3 |
Sn1a—C9a—H9a2 | 105.1 | C28b—C27b—H27d | 109.3 |
H9a1—C9a—H9a2 | 105.9 | H27c—C27b—H27d | 107.9 |
C9a—C10a—H10a | 110.2 | C29b—C28b—H28c | 109.5 |
C11a—C10a—H10a | 110.2 | C27b—C28b—H28c | 109.5 |
C9a—C10a—H10b | 110.2 | C29b—C28b—H28d | 109.5 |
C11a—C10a—H10b | 110.2 | C27b—C28b—H28d | 109.5 |
H10a—C10a—H10b | 108.5 | H28c—C28b—H28d | 108.1 |
C10a—C11a—H11a | 111.6 | C28b—C29b—H29c | 109.0 |
C12a—C11a—H11a | 111.6 | C30b—C29b—H29c | 109.0 |
C10a—C11a—H11b | 111.6 | C28b—C29b—H29d | 109.0 |
C12a—C11a—H11b | 111.6 | C30b—C29b—H29d | 109.0 |
H11a—C11a—H11b | 109.4 | H29c—C29b—H29d | 107.8 |
C11a—C12a—H12a | 109.5 | C29b—C30b—H30c | 109.9 |
C11a—C12a—H12b | 109.5 | C31b—C30b—H30c | 109.9 |
H12a—C12a—H12b | 109.5 | C29b—C30b—H30d | 109.9 |
C11a—C12a—H12c | 109.5 | C31b—C30b—H30d | 109.9 |
H12a—C12a—H12c | 109.5 | H30c—C30b—H30d | 108.3 |
H12b—C12a—H12c | 109.5 | C26b—C31b—H31c | 109.6 |
C14a—C15a—H15a | 119.2 | C30b—C31b—H31c | 109.6 |
C16a—C15a—H15a | 119.2 | C26b—C31b—H31d | 109.6 |
C18a—C17a—H17a | 119.2 | C30b—C31b—H31d | 109.6 |
C16a—C17a—H17a | 119.2 | H31c—C31b—H31d | 108.1 |
| | | |
C9a—Sn1a—O1a—C13a | −58.3 (6) | C9b—Sn1b—O1b—C13b | 58.0 (8) |
C1a—Sn1a—O1a—C13a | −175.4 (6) | C5b—Sn1b—O1b—C13b | −67.2 (8) |
C5a—Sn1a—O1a—C13a | 66.4 (6) | C1b—Sn1b—O1b—C13b | 177.1 (8) |
O3ai—Sn1a—O1a—C13a | −108 (2) | O3bii—Sn1b—O1b—C13b | 149 (3) |
C9a—Sn1a—C1a—C2a | −11 (1) | C9b—Sn1b—C1b—C2b | 33 (1) |
C5a—Sn1a—C1a—C2a | 166.8 (9) | C5b—Sn1b—C1b—C2b | −147 (1) |
O1a—Sn1a—C1a—C2a | 76.9 (9) | O1b—Sn1b—C1b—C2b | −60 (1) |
O3ai—Sn1a—C1a—C2a | −97.8 (9) | O3bii—Sn1b—C1b—C2b | 118 (1) |
Sn1a—C1a—C2a—C3a | −174 (1) | Sn1b—C1b—C2b—C3b | 167 (2) |
C1a—C2a—C3a—C4a | −170 (1) | C1b—C2b—C3b—C4b | −175 (2) |
C9a—Sn1a—C5a—C6a | 155.2 (9) | C9b—Sn1b—C5b—C6b | −157.5 (8) |
C1a—Sn1a—C5a—C6a | −23 (1) | C1b—Sn1b—C5b—C6b | 22.7 (9) |
O1a—Sn1a—C5a—C6a | 64.2 (9) | O1b—Sn1b—C5b—C6b | −64.0 (8) |
O3ai—Sn1a—C5a—C6a | −116.4 (9) | O3bii—Sn1b—C5b—C6b | 113.6 (8) |
Sn1a—C5a—C6a—C7a | 177 (1) | Sn1b—C5b—C6b—C7b | 173 (1) |
C5a—C6a—C7a—C8a | −166 (2) | C5b—C6b—C7b—C8b | 166 (1) |
C1a—Sn1a—C9a—C10a | −129 (1) | C5b—Sn1b—C9b—C10b | −22 (1) |
C5a—Sn1a—C9a—C10a | 54 (1) | C1b—Sn1b—C9b—C10b | 158.0 (8) |
O1a—Sn1a—C9a—C10a | 146 (1) | O1b—Sn1b—C9b—C10b | −112.4 (8) |
O3ai—Sn1a—C9a—C10a | −39 (1) | O3bii—Sn1b—C9b—C10b | 71.6 (8) |
Sn1a—C9a—C10a—C11a | −58 (2) | Sn1b—C9b—C10b—C11b | −175.8 (9) |
C9a—C10a—C11a—C12a | 163 (2) | C9b—C10b—C11b—C12b | −175 (1) |
Sn1a—O1a—C13a—O2a | −6 (1) | Sn1b—O1b—C13b—O2b | −3 (1) |
Sn1a—O1a—C13a—C14a | 176.4 (4) | Sn1b—O1b—C13b—C14b | 175.6 (5) |
C18a—O5a—C14a—C15a | −2.4 (8) | C18b—O5b—C14b—C15b | 3.9 (9) |
C18a—O5a—C14a—C13a | 177.1 (5) | C18b—O5b—C14b—C13b | −176.9 (6) |
O2a—C13a—C14a—C15a | −175.6 (6) | O2b—C13b—C14b—C15b | 169.0 (8) |
O1a—C13a—C14a—C15a | 2 (1) | O1b—C13b—C14b—C15b | −10 (1) |
O2a—C13a—C14a—O5a | 4.9 (8) | O2b—C13b—C14b—O5b | −10 (1) |
O1a—C13a—C14a—O5a | −177.2 (5) | O1b—C13b—C14b—O5b | 170.7 (6) |
O5a—C14a—C15a—C16a | −2 (1) | O5b—C14b—C15b—C16b | 0 (1) |
C13a—C14a—C15a—C16a | 178.9 (6) | C13b—C14b—C15b—C16b | −179.4 (7) |
C14a—C15a—C16a—O6a | −174.2 (7) | C14b—C15b—C16b—O6b | 174.5 (7) |
C14a—C15a—C16a—C17a | 5.2 (9) | C14b—C15b—C16b—C17b | −3 (1) |
O6a—C16a—C17a—C18a | 174.3 (7) | O6b—C16b—C17b—C18b | −174.1 (7) |
C15a—C16a—C17a—C18a | −5 (1) | C15b—C16b—C17b—C18b | 4 (1) |
C16a—C17a—C18a—O5a | 2 (1) | C16b—C17b—C18b—O5b | −1 (1) |
C16a—C17a—C18a—C19a | −179.4 (6) | C16b—C17b—C18b—C19b | −179.9 (7) |
C14a—O5a—C18a—C17a | 2.5 (9) | C14b—O5b—C18b—C17b | −3.4 (9) |
C14a—O5a—C18a—C19a | −176.7 (5) | C14b—O5b—C18b—C19b | 176.0 (5) |
Sn1aii—O3a—C19a—O4a | 9 (1) | Sn1bi—O3b—C19b—O4b | −12 (1) |
Sn1aii—O3a—C19a—C18a | −170.7 (4) | Sn1bi—O3b—C19b—C18b | 166.1 (4) |
C17a—C18a—C19a—O4a | 168.5 (8) | C17b—C18b—C19b—O4b | −176.0 (7) |
O5a—C18a—C19a—O4a | −12 (1) | O5b—C18b—C19b—O4b | 5 (1) |
C17a—C18a—C19a—O3a | −12 (1) | C17b—C18b—C19b—O3b | 6 (1) |
O5a—C18a—C19a—O3a | 167.6 (6) | O5b—C18b—C19b—O3b | −173.4 (6) |
C26a—N1a—C20a—C21a | −72.8 (7) | C26b—N1b—C20b—C21b | −65.3 (8) |
C26a—N1a—C20a—C25a | 165.1 (6) | C26b—N1b—C20b—C25b | 172.4 (6) |
N1a—C20a—C21a—C22a | −177.4 (6) | N1b—C20b—C21b—C22b | 178.2 (7) |
C25a—C20a—C21a—C22a | −56.5 (9) | C25b—C20b—C21b—C22b | −59.1 (9) |
C20a—C21a—C22a—C23a | 56 (1) | C20b—C21b—C22b—C23b | 59 (1) |
C21a—C22a—C23a—C24a | −57 (1) | C21b—C22b—C23b—C24b | −57 (1) |
C22a—C23a—C24a—C25a | 58 (1) | C22b—C23b—C24b—C25b | 56 (1) |
N1a—C20a—C25a—C24a | 179.2 (7) | C23b—C24b—C25b—C20b | −57 (1) |
C21a—C20a—C25a—C24a | 56.9 (9) | N1b—C20b—C25b—C24b | −177.7 (6) |
C23a—C24a—C25a—C20a | −58 (1) | C21b—C20b—C25b—C24b | 58.2 (9) |
C20a—N1a—C26a—C27a | 162.1 (6) | C20b—N1b—C26b—C27b | −59.3 (8) |
C20a—N1a—C26a—C31a | −75.0 (7) | C20b—N1b—C26b—C31b | 175.1 (7) |
N1a—C26a—C27a—C28a | −179.4 (8) | N1b—C26b—C27b—C28b | −175.4 (7) |
C31a—C26a—C27a—C28a | 58 (1) | C31b—C26b—C27b—C28b | −53 (1) |
C26a—C27a—C28a—C29a | −59 (1) | C26b—C27b—C28b—C29b | 51 (1) |
C27a—C28a—C29a—C30a | 58 (1) | C27b—C28b—C29b—C30b | −55 (1) |
C28a—C29a—C30a—C31a | −56 (1) | C28b—C29b—C30b—C31b | 58 (2) |
N1a—C26a—C31a—C30a | −176.0 (6) | N1b—C26b—C31b—C30b | 179.9 (9) |
C27a—C26a—C31a—C30a | −55.0 (9) | C27b—C26b—C31b—C30b | 55 (1) |
C29a—C30a—C31a—C26a | 54 (1) | C29b—C30b—C31b—C26b | −56 (1) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1a—H1a1···O2a | 0.90 | 1.89 | 2.785 (7) | 172 |
N1a—H1a2···O4a | 0.90 | 1.90 | 2.788 (7) | 169 |
N1b—H1b2···O2b | 0.90 | 1.89 | 2.786 (8) | 171 |
N1b—H1b1···O4b | 0.90 | 1.87 | 2.765 (7) | 172 |
(II) Methylphenylammonium 2,6-pyridinedicarboxylatotributylstannate
top
Crystal data top
(C7H10N)[Sn(C7H3NO4)(C4H9)3] | F(000) = 1168 |
Mr = 563.29 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 17.7536 (3) Å | Cell parameters from 5832 reflections |
b = 9.3746 (1) Å | θ = 2.8–28.3° |
c = 17.8985 (2) Å | µ = 0.91 mm−1 |
β = 102.981 (1)° | T = 298 K |
V = 2902.77 (7) Å3 | Block, colorless |
Z = 4 | 0.44 × 0.22 × 0.18 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 7133 independent reflections |
Radiation source: fine-focus sealed tube | 4770 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scan | θmax = 28.3°, θmin = 2.8° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −23→12 |
Tmin = 0.690, Tmax = 0.853 | k = −12→12 |
19786 measured reflections | l = −23→23 |
Refinement top
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0751P)2 + 0.3874P] where P = (Fo2 + 2Fc2)/3 |
7133 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 0.88 e Å−3 |
20 restraints | Δρmin = −1.08 e Å−3 |
Crystal data top
(C7H10N)[Sn(C7H3NO4)(C4H9)3] | V = 2902.77 (7) Å3 |
Mr = 563.29 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 17.7536 (3) Å | µ = 0.91 mm−1 |
b = 9.3746 (1) Å | T = 298 K |
c = 17.8985 (2) Å | 0.44 × 0.22 × 0.18 mm |
β = 102.981 (1)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 7133 independent reflections |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | 4770 reflections with I > 2σ(I) |
Tmin = 0.690, Tmax = 0.853 | Rint = 0.059 |
19786 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 20 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.88 e Å−3 |
7133 reflections | Δρmin = −1.08 e Å−3 |
307 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Sn1 | 0.41074 (2) | 0.25654 (2) | 0.21949 (1) | 0.0460 (1) | |
O1 | 0.4960 (2) | 0.1554 (3) | 0.3195 (2) | 0.061 (1) | |
O2 | 0.5899 (2) | 0.3179 (4) | 0.3319 (2) | 0.071 (1) | |
O3 | 0.8179 (2) | 0.1391 (3) | 0.6270 (1) | 0.062 (1) | |
O4 | 0.8014 (2) | 0.3116 (4) | 0.5384 (2) | 0.068 (1) | |
N1 | 0.6707 (2) | 0.1854 (4) | 0.4594 (2) | 0.043 (1) | |
N2 | 0.7288 (2) | 0.4356 (4) | 0.4011 (2) | 0.072 (1) | |
C1 | 0.3293 (3) | 0.0980 (5) | 0.2371 (3) | 0.070 (1) | |
C2 | 0.353 (3) | −0.058 (2) | 0.247 (2) | 0.115 (3) | 0.50 |
C3 | 0.392 (2) | −0.109 (2) | 0.185 (1) | 0.125 (5) | 0.50 |
C4 | 0.363 (2) | −0.248 (2) | 0.146 (1) | 0.138 (7) | 0.50 |
C2' | 0.355 (3) | −0.051 (2) | 0.264 (1) | 0.115 (3) | 0.50 |
C3' | 0.393 (2) | −0.138 (2) | 0.211 (1) | 0.125 (5) | 0.50 |
C4' | 0.342 (2) | −0.160 (2) | 0.131 (1) | 0.138 (7) | 0.50 |
C5 | 0.4090 (3) | 0.4525 (4) | 0.2817 (2) | 0.064 (1) | |
C6 | 0.3986 (3) | 0.4362 (5) | 0.3629 (3) | 0.077 (1) | |
C7 | 0.3933 (3) | 0.5779 (5) | 0.4035 (3) | 0.084 (2) | |
C8 | 0.4653 (4) | 0.6663 (7) | 0.4168 (3) | 0.098 (2) | |
C9 | 0.4870 (3) | 0.2310 (5) | 0.1452 (3) | 0.067 (1) | |
C10 | 0.5293 (4) | 0.3638 (7) | 0.1289 (3) | 0.098 (2) | |
C11 | 0.5839 (5) | 0.3339 (9) | 0.0762 (5) | 0.140 (3) | |
C12 | 0.6285 (6) | 0.461 (1) | 0.0600 (6) | 0.193 (5) | |
C13 | 0.5612 (2) | 0.2092 (4) | 0.3517 (2) | 0.049 (1) | |
C14 | 0.6050 (2) | 0.1260 (4) | 0.4218 (2) | 0.042 (1) | |
C15 | 0.5768 (2) | 0.0004 (4) | 0.4441 (2) | 0.055 (1) | |
C16 | 0.6181 (3) | −0.0649 (5) | 0.5094 (3) | 0.069 (1) | |
C17 | 0.6860 (2) | −0.0047 (4) | 0.5498 (2) | 0.055 (1) | |
C18 | 0.7104 (2) | 0.1210 (4) | 0.5227 (2) | 0.042 (1) | |
C19 | 0.7829 (2) | 0.1973 (5) | 0.5650 (2) | 0.049 (1) | |
C20 | 0.7123 (4) | 0.5856 (6) | 0.4216 (4) | 0.107 (2) | |
C21 | 0.7805 (3) | 0.4203 (6) | 0.3492 (3) | 0.076 (1) | |
C22 | 0.7579 (4) | 0.469 (1) | 0.2747 (4) | 0.128 (3) | |
C23 | 0.8104 (6) | 0.448 (1) | 0.2269 (4) | 0.165 (4) | |
C24 | 0.8784 (6) | 0.390 (1) | 0.2507 (5) | 0.132 (3) | |
C25 | 0.9001 (5) | 0.341 (1) | 0.3240 (6) | 0.146 (3) | |
C26 | 0.8496 (4) | 0.3622 (9) | 0.3739 (4) | 0.126 (3) | |
H2a | 0.7493 | 0.3883 | 0.4446 | 0.108* | |
H2b | 0.6836 | 0.3932 | 0.3797 | 0.108* | |
H1a | 0.3114 | 0.1256 | 0.2824 | 0.105* | |
H1b | 0.2851 | 0.1036 | 0.1941 | 0.105* | |
H2c | 0.3881 | −0.0704 | 0.2964 | 0.172* | 0.50 |
H2d | 0.3077 | −0.1157 | 0.2457 | 0.172* | 0.50 |
H3a | 0.4472 | −0.1192 | 0.2075 | 0.188* | 0.50 |
H3b | 0.3870 | −0.0350 | 0.1461 | 0.188* | 0.50 |
H4a | 0.3917 | −0.2694 | 0.1072 | 0.208* | 0.50 |
H4b | 0.3093 | −0.2392 | 0.1219 | 0.208* | 0.50 |
H4c | 0.3704 | −0.3235 | 0.1828 | 0.208* | 0.50 |
H2'1 | 0.3110 | −0.1029 | 0.2725 | 0.172* | 0.50 |
H2'2 | 0.3920 | −0.0427 | 0.3131 | 0.172* | 0.50 |
H3'1 | 0.4069 | −0.2302 | 0.2341 | 0.188* | 0.50 |
H3'2 | 0.4400 | −0.0905 | 0.2060 | 0.188* | 0.50 |
H4'1 | 0.3705 | −0.2131 | 0.1003 | 0.208* | 0.50 |
H4'2 | 0.3273 | −0.0697 | 0.1073 | 0.208* | 0.50 |
H4'3 | 0.2967 | −0.2130 | 0.1346 | 0.208* | 0.50 |
H5a | 0.4571 | 0.5028 | 0.2834 | 0.095* | |
H5b | 0.3674 | 0.5116 | 0.2534 | 0.095* | |
H6a | 0.4417 | 0.3820 | 0.3924 | 0.115* | |
H6b | 0.3518 | 0.3820 | 0.3619 | 0.115* | |
H7a | 0.3511 | 0.6330 | 0.3732 | 0.126* | |
H7b | 0.3809 | 0.5586 | 0.4526 | 0.126* | |
H8a | 0.4572 | 0.7534 | 0.4421 | 0.147* | |
H8b | 0.4776 | 0.6880 | 0.3685 | 0.147* | |
H8c | 0.5072 | 0.6143 | 0.4483 | 0.147* | |
H9a | 0.5251 | 0.1596 | 0.1670 | 0.101* | |
H9b | 0.4577 | 0.1939 | 0.0967 | 0.101* | |
H10a | 0.5586 | 0.4025 | 0.1770 | 0.147* | |
H10b | 0.4918 | 0.4351 | 0.1054 | 0.147* | |
H11a | 0.6201 | 0.2603 | 0.0994 | 0.211* | |
H11b | 0.5540 | 0.2969 | 0.0280 | 0.211* | |
H12a | 0.6610 | 0.4336 | 0.0262 | 0.290* | |
H12b | 0.6599 | 0.4961 | 0.1071 | 0.290* | |
H12c | 0.5933 | 0.5337 | 0.0363 | 0.290* | |
H15 | 0.5312 | −0.0393 | 0.4159 | 0.082* | |
H16 | 0.6002 | −0.1495 | 0.5264 | 0.103* | |
H17 | 0.7145 | −0.0475 | 0.5940 | 0.082* | |
H20a | 0.6777 | 0.5843 | 0.4559 | 0.161* | |
H20b | 0.6888 | 0.6370 | 0.3759 | 0.161* | |
H20c | 0.7597 | 0.6316 | 0.4461 | 0.161* | |
H22 | 0.7105 | 0.5133 | 0.2568 | 0.192* | |
H23 | 0.7957 | 0.4769 | 0.1759 | 0.248* | |
H24 | 0.9119 | 0.3821 | 0.2177 | 0.198* | |
H25 | 0.9472 | 0.2953 | 0.3410 | 0.219* | |
H26 | 0.8652 | 0.3346 | 0.4249 | 0.189* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0373 (2) | 0.0584 (2) | 0.0354 (2) | 0.0001 (1) | −0.0064 (1) | −0.0043 (1) |
O1 | 0.047 (2) | 0.067 (2) | 0.054 (2) | −0.001 (1) | −0.019 (1) | 0.003 (1) |
O2 | 0.052 (2) | 0.090 (2) | 0.058 (2) | −0.012 (2) | −0.014 (1) | 0.030 (2) |
O3 | 0.058 (2) | 0.074 (2) | 0.039 (1) | −0.010 (2) | −0.017 (1) | 0.005 (1) |
O4 | 0.060 (2) | 0.079 (2) | 0.054 (2) | −0.026 (2) | −0.013 (1) | 0.011 (2) |
N1 | 0.039 (2) | 0.054 (2) | 0.031 (1) | −0.004 (1) | −0.003 (1) | −0.001 (1) |
N2 | 0.062 (2) | 0.083 (3) | 0.064 (2) | −0.023 (2) | 0.000 (2) | 0.026 (2) |
C1 | 0.057 (3) | 0.084 (3) | 0.066 (3) | −0.007 (2) | 0.005 (2) | 0.004 (2) |
C2 | 0.105 (6) | 0.096 (5) | 0.15 (1) | −0.025 (5) | 0.037 (9) | −0.009 (6) |
C3 | 0.157 (8) | 0.091 (7) | 0.16 (2) | −0.031 (7) | 0.09 (1) | 0.005 (8) |
C4 | 0.16 (2) | 0.15 (2) | 0.10 (1) | −0.04 (2) | 0.02 (1) | 0.00 (1) |
C2' | 0.105 (6) | 0.096 (5) | 0.15 (1) | −0.025 (5) | 0.037 (9) | −0.009 (6) |
C3' | 0.157 (8) | 0.091 (7) | 0.16 (2) | −0.031 (7) | 0.09 (1) | 0.005 (8) |
C4' | 0.16 (2) | 0.15 (2) | 0.10 (1) | −0.04 (2) | 0.02 (1) | 0.00 (1) |
C5 | 0.075 (3) | 0.058 (2) | 0.047 (2) | 0.002 (2) | −0.009 (2) | −0.006 (2) |
C6 | 0.089 (4) | 0.072 (3) | 0.075 (3) | −0.019 (3) | 0.030 (3) | −0.022 (2) |
C7 | 0.084 (4) | 0.081 (3) | 0.088 (3) | −0.004 (3) | 0.025 (3) | −0.030 (3) |
C8 | 0.095 (4) | 0.110 (4) | 0.089 (4) | −0.030 (4) | 0.020 (3) | −0.039 (3) |
C9 | 0.058 (3) | 0.086 (3) | 0.059 (3) | −0.002 (2) | 0.014 (2) | 0.000 (2) |
C10 | 0.095 (4) | 0.123 (5) | 0.079 (4) | −0.020 (4) | 0.024 (3) | 0.009 (3) |
C11 | 0.161 (8) | 0.148 (7) | 0.141 (7) | −0.021 (6) | 0.094 (6) | 0.007 (6) |
C12 | 0.170 (9) | 0.26 (1) | 0.159 (8) | −0.071 (9) | 0.057 (7) | 0.074 (8) |
C13 | 0.040 (2) | 0.060 (2) | 0.038 (2) | 0.001 (2) | −0.007 (2) | 0.001 (2) |
C14 | 0.036 (2) | 0.052 (2) | 0.033 (2) | −0.001 (2) | −0.003 (1) | −0.003 (1) |
C15 | 0.044 (2) | 0.059 (2) | 0.053 (2) | −0.014 (2) | −0.006 (2) | 0.001 (2) |
C16 | 0.062 (3) | 0.063 (2) | 0.068 (3) | −0.015 (2) | −0.012 (2) | 0.022 (2) |
C17 | 0.054 (2) | 0.056 (2) | 0.046 (2) | −0.004 (2) | −0.004 (2) | 0.013 (2) |
C18 | 0.036 (2) | 0.054 (2) | 0.032 (2) | −0.002 (2) | 0.001 (1) | −0.002 (1) |
C19 | 0.040 (2) | 0.066 (2) | 0.036 (2) | −0.005 (2) | −0.004 (2) | −0.001 (2) |
C20 | 0.118 (5) | 0.087 (4) | 0.119 (5) | −0.008 (4) | 0.031 (4) | 0.015 (3) |
C21 | 0.065 (3) | 0.086 (3) | 0.072 (3) | −0.027 (3) | 0.001 (3) | 0.019 (2) |
C22 | 0.087 (5) | 0.219 (9) | 0.076 (4) | −0.011 (5) | 0.014 (3) | 0.045 (5) |
C23 | 0.125 (7) | 0.29 (1) | 0.085 (5) | −0.040 (9) | 0.022 (5) | 0.047 (6) |
C24 | 0.125 (7) | 0.167 (8) | 0.114 (6) | −0.038 (6) | 0.051 (5) | −0.003 (5) |
C25 | 0.116 (6) | 0.172 (8) | 0.167 (8) | 0.023 (6) | 0.069 (6) | 0.065 (7) |
C26 | 0.101 (5) | 0.167 (7) | 0.116 (5) | 0.020 (5) | 0.036 (4) | 0.073 (5) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.146 (5) | C2—H2d | 0.9700 |
Sn1—C5 | 2.152 (4) | C3—H3a | 0.9700 |
Sn1—C9 | 2.113 (5) | C3—H3b | 0.9700 |
Sn1—O1 | 2.275 (2) | C4—H4a | 0.9600 |
Sn1—O3i | 2.279 (2) | C4—H4b | 0.9600 |
O1—C13 | 1.275 (5) | C4—H4c | 0.9600 |
O2—C13 | 1.226 (5) | C2'—H2'1 | 0.9700 |
O3—C19 | 1.266 (4) | C2'—H2'2 | 0.9700 |
O4—C19 | 1.247 (5) | C3'—H3'1 | 0.9700 |
N1—C14 | 1.332 (4) | C3'—H3'2 | 0.9700 |
N1—C18 | 1.336 (4) | C4'—H4'1 | 0.9600 |
N2—C21 | 1.452 (7) | C4'—H4'2 | 0.9600 |
N2—C20 | 1.499 (7) | C4'—H4'3 | 0.9600 |
C1—C2 | 1.519 (9) | C5—H5a | 0.9700 |
C2—C3 | 1.511 (9) | C5—H5b | 0.9700 |
C3—C4 | 1.518 (9) | C6—H6a | 0.9700 |
C1—C2' | 1.513 (9) | C6—H6b | 0.9700 |
C2'—C3' | 1.515 (9) | C7—H7a | 0.9700 |
C3'—C4' | 1.53 (1) | C7—H7b | 0.9700 |
C5—C6 | 1.514 (5) | C8—H8a | 0.9600 |
C6—C7 | 1.527 (5) | C8—H8b | 0.9600 |
C7—C8 | 1.496 (6) | C8—H8c | 0.9600 |
C9—C10 | 1.516 (6) | C9—H9a | 0.9700 |
C10—C11 | 1.523 (7) | C9—H9b | 0.9700 |
C11—C12 | 1.492 (8) | C10—H10a | 0.9700 |
C13—C14 | 1.533 (5) | C10—H10b | 0.9700 |
C14—C15 | 1.373 (5) | C11—H11a | 0.9700 |
C15—C16 | 1.377 (6) | C11—H11b | 0.9700 |
C16—C17 | 1.379 (6) | C12—H12a | 0.9600 |
C17—C18 | 1.380 (5) | C12—H12b | 0.9600 |
C18—C19 | 1.518 (5) | C12—H12c | 0.9600 |
C21—C26 | 1.324 (8) | C15—H15 | 0.9300 |
C21—C22 | 1.381 (8) | C16—H16 | 0.9300 |
C22—C23 | 1.41 (1) | C17—H17 | 0.9300 |
C23—C24 | 1.31 (1) | C20—H20a | 0.9600 |
C24—C25 | 1.36 (1) | C20—H20b | 0.9600 |
C25—C26 | 1.41 (1) | C20—H20c | 0.9600 |
N2—H2a | 0.9000 | C22—H22 | 0.9300 |
N2—H2b | 0.9000 | C23—H23 | 0.9300 |
C1—H1a | 0.9700 | C24—H24 | 0.9300 |
C1—H1b | 0.9700 | C25—H25 | 0.9300 |
C2—H2c | 0.9700 | C26—H26 | 0.9300 |
| | | |
C1—Sn1—C5 | 115.3 (2) | H2'1—C2'—H2'2 | 107.4 |
C1—Sn1—C9 | 124.2 (2) | C2'—C3'—H3'1 | 108.6 |
C1—Sn1—O1 | 87.0 (1) | C4'—C3'—H3'1 | 108.6 |
C1—Sn1—O3i | 90.2 (2) | C2'—C3'—H3'2 | 108.6 |
C5—Sn1—C9 | 120.5 (2) | C4'—C3'—H3'2 | 108.6 |
C5—Sn1—O1 | 91.9 (1) | H3'1—C3'—H3'2 | 107.6 |
C5—Sn1—O3i | 85.3 (1) | C3'—C4'—H4'1 | 109.5 |
C9—Sn1—O1 | 92.3 (2) | C3'—C4'—H4'2 | 109.5 |
C9—Sn1—O3i | 93.0 (2) | H4'1—C4'—H4'2 | 109.5 |
O1—Sn1—O3i | 174.7 (1) | C3'—C4'—H4'3 | 109.5 |
C13—O1—Sn1 | 124.5 (3) | H4'1—C4'—H4'3 | 109.5 |
C19—O3—Sn1ii | 125.7 (3) | H4'2—C4'—H4'3 | 109.5 |
C14—N1—C18 | 118.3 (3) | C6—C5—H5a | 108.4 |
C21—N2—C20 | 115.9 (4) | Sn1—C5—H5a | 108.4 |
C2—C1—Sn1 | 120 (2) | C6—C5—H5b | 108.4 |
C3—C2—C1 | 113 (1) | Sn1—C5—H5b | 108.4 |
C2—C3—C4 | 117 (1) | H5a—C5—H5b | 107.5 |
C2'—C1—Sn1 | 121 (1) | C5—C6—H6a | 108.8 |
C3'—C2'—C1 | 116 (1) | C7—C6—H6a | 108.8 |
C2'—C3'—C4' | 115 (1) | C5—C6—H6b | 108.8 |
C6—C5—Sn1 | 115.5 (3) | C7—C6—H6b | 108.8 |
C5—C6—C7 | 113.8 (4) | H6a—C6—H6b | 107.7 |
C8—C7—C6 | 114.6 (5) | C8—C7—H7a | 108.6 |
C10—C9—Sn1 | 116.3 (3) | C6—C7—H7a | 108.6 |
C9—C10—C11 | 112.3 (5) | C8—C7—H7b | 108.6 |
C12—C11—C10 | 114.4 (7) | C6—C7—H7b | 108.6 |
O2—C13—O1 | 126.3 (3) | H7a—C7—H7b | 107.6 |
O2—C13—C14 | 119.5 (3) | C7—C8—H8a | 109.5 |
O1—C13—C14 | 114.2 (3) | C7—C8—H8b | 109.5 |
N1—C14—C15 | 123.2 (3) | H8a—C8—H8b | 109.5 |
N1—C14—C13 | 115.2 (3) | C7—C8—H8c | 109.5 |
C15—C14—C13 | 121.6 (3) | H8a—C8—H8c | 109.5 |
C16—C15—C14 | 118.0 (3) | H8b—C8—H8c | 109.5 |
C17—C16—C15 | 119.9 (4) | C10—C9—H9a | 108.2 |
C16—C17—C18 | 118.1 (3) | Sn1—C9—H9a | 108.2 |
N1—C18—C17 | 122.5 (3) | C10—C9—H9b | 108.2 |
N1—C18—C19 | 115.8 (3) | Sn1—C9—H9b | 108.2 |
C17—C18—C19 | 121.6 (3) | H9a—C9—H9b | 107.4 |
O4—C19—O3 | 125.8 (3) | C9—C10—H10a | 109.1 |
O4—C19—C18 | 118.8 (3) | C11—C10—H10a | 109.1 |
O3—C19—C18 | 115.3 (4) | C9—C10—H10b | 109.1 |
C26—C21—C22 | 120.2 (6) | C11—C10—H10b | 109.1 |
C26—C21—N2 | 119.9 (5) | H10a—C10—H10b | 107.9 |
C22—C21—N2 | 119.8 (5) | C12—C11—H11a | 108.7 |
C21—C22—C23 | 116.9 (7) | C10—C11—H11a | 108.7 |
C24—C23—C22 | 123.2 (8) | C12—C11—H11b | 108.7 |
C23—C24—C25 | 119.6 (8) | C10—C11—H11b | 108.7 |
C24—C25—C26 | 118.8 (8) | H11a—C11—H11b | 107.6 |
C21—C26—C25 | 121.2 (7) | C11—C12—H12a | 109.5 |
C21—N2—H2a | 108.3 | C11—C12—H12b | 109.5 |
C20—N2—H2a | 108.3 | H12a—C12—H12b | 109.5 |
C21—N2—H2b | 108.3 | C11—C12—H12c | 109.5 |
C20—N2—H2b | 108.3 | H12a—C12—H12c | 109.5 |
H2a—N2—H2b | 107.4 | H12b—C12—H12c | 109.5 |
C2—C1—H1a | 107.3 | C16—C15—H15 | 121.0 |
Sn1—C1—H1a | 107.3 | C14—C15—H15 | 121.0 |
C2—C1—H1b | 107.3 | C17—C16—H16 | 120.0 |
Sn1—C1—H1b | 107.3 | C15—C16—H16 | 120.0 |
H1a—C1—H1b | 106.9 | C16—C17—H17 | 120.9 |
C3—C2—H2c | 109.1 | C18—C17—H17 | 120.9 |
C1—C2—H2c | 109.1 | N2—C20—H20a | 109.5 |
C3—C2—H2d | 109.1 | N2—C20—H20b | 109.5 |
C1—C2—H2d | 109.1 | H20a—C20—H20b | 109.5 |
H2c—C2—H2d | 107.8 | N2—C20—H20c | 109.5 |
C2—C3—H3a | 108.1 | H20a—C20—H20c | 109.5 |
C4—C3—H3a | 108.1 | H20b—C20—H20c | 109.5 |
C2—C3—H3b | 108.1 | C21—C22—H22 | 121.6 |
C4—C3—H3b | 108.1 | C23—C22—H22 | 121.6 |
H3a—C3—H3b | 107.3 | C24—C23—H23 | 118.4 |
C3—C4—H4a | 109.5 | C22—C23—H23 | 118.4 |
C3—C4—H4b | 109.5 | C23—C24—H24 | 120.2 |
H4a—C4—H4b | 109.5 | C25—C24—H24 | 120.2 |
C3—C4—H4c | 109.5 | C24—C25—H25 | 120.6 |
H4a—C4—H4c | 109.5 | C26—C25—H25 | 120.6 |
H4b—C4—H4c | 109.5 | C21—C26—H26 | 119.4 |
C3'—C2'—H2'1 | 108.2 | C25—C26—H26 | 119.4 |
C3'—C2'—H2'2 | 108.2 | | |
| | | |
C9—Sn1—O1—C13 | 65.7 (4) | O1—C13—C14—N1 | −175.6 (3) |
C1—Sn1—O1—C13 | −170.1 (4) | O2—C13—C14—C15 | −177.0 (4) |
C5—Sn1—O1—C13 | −54.9 (4) | O1—C13—C14—C15 | 3.4 (6) |
O3i—Sn1—O1—C13 | −113 (1) | N1—C14—C15—C16 | 1.4 (6) |
C9—Sn1—C1—C2 | 43 (1) | C13—C14—C15—C16 | −177.5 (4) |
C5—Sn1—C1—C2 | −138 (1) | C14—C15—C16—C17 | −0.7 (7) |
O1—Sn1—C1—C2 | −48 (1) | C15—C16—C17—C18 | 0.0 (7) |
O3i—Sn1—C1—C2 | 137 (1) | C14—N1—C18—C17 | 0.5 (5) |
Sn1—C1—C2—C3 | −50 (3) | C14—N1—C18—C19 | −177.3 (3) |
C1—C2—C3—C4 | −131 (3) | C16—C17—C18—N1 | 0.1 (6) |
C9—Sn1—C5—C6 | −141.5 (4) | C16—C17—C18—C19 | 177.8 (4) |
C1—Sn1—C5—C6 | 39.9 (4) | Sn1ii—O3—C19—O4 | 12.1 (7) |
O1—Sn1—C5—C6 | −47.6 (4) | Sn1ii—O3—C19—C18 | −165.1 (2) |
O3i—Sn1—C5—C6 | 127.9 (4) | N1—C18—C19—O4 | −1.0 (6) |
Sn1—C5—C6—C7 | −176.9 (4) | C17—C18—C19—O4 | −178.9 (4) |
C5—C6—C7—C8 | −64.7 (7) | N1—C18—C19—O3 | 176.5 (4) |
C1—Sn1—C9—C10 | 168.9 (4) | C17—C18—C19—O3 | −1.4 (6) |
C5—Sn1—C9—C10 | −9.6 (5) | C20—N2—C21—C26 | 113.0 (7) |
O1—Sn1—C9—C10 | −103.2 (4) | C20—N2—C21—C22 | −65.8 (7) |
O3i—Sn1—C9—C10 | 76.7 (4) | C26—C21—C22—C23 | 3 (1) |
Sn1—C9—C10—C11 | 178.8 (5) | N2—C21—C22—C23 | −178.8 (8) |
C9—C10—C11—C12 | −178.6 (7) | C21—C22—C23—C24 | −2 (2) |
Sn1—O1—C13—O2 | −4.2 (7) | C22—C23—C24—C25 | 3 (2) |
Sn1—O1—C13—C14 | 175.4 (2) | C23—C24—C25—C26 | −4 (2) |
C18—N1—C14—C15 | −1.3 (5) | C22—C21—C26—C25 | −4 (1) |
C18—N1—C14—C13 | 177.7 (3) | N2—C21—C26—C25 | 177.8 (7) |
O2—C13—C14—N1 | 4.0 (6) | C24—C25—C26—C21 | 4 (2) |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2b···O2 | 0.90 | 1.83 | 2.732 (5) | 176 |
N2—H2a···O4 | 0.90 | 1.87 | 2.763 (4) | 172 |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | (C12H24N)[Sn(C7H2O6)(C4H9)3] | (C7H10N)[Sn(C7H3NO4)(C4H9)3] |
Mr | 654.43 | 563.29 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 298 | 298 |
a, b, c (Å) | 18.1212 (3), 18.0363 (2), 21.8937 (1) | 17.7536 (3), 9.3746 (1), 17.8985 (2) |
β (°) | 98.454 (1) | 102.981 (1) |
V (Å3) | 7078.0 (1) | 2902.77 (7) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.76 | 0.91 |
Crystal size (mm) | 0.38 × 0.24 × 0.20 | 0.44 × 0.22 × 0.18 |
|
Data collection |
Diffractometer | Siemens CCD area-detector diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (SADABS; Sheldrick, 1996) | Empirical (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.761, 0.863 | 0.690, 0.853 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36773, 12367, 6929 | 19786, 7133, 4770 |
Rint | 0.055 | 0.059 |
(sin θ/λ)max (Å−1) | 0.595 | 0.666 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.189, 1.07 | 0.049, 0.155, 1.06 |
No. of reflections | 12367 | 7133 |
No. of parameters | 703 | 307 |
No. of restraints | 330 | 20 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −0.43 | 0.88, −1.08 |
Selected geometric parameters (Å, º) for (I) topSn1a—C1a | 2.127 (9) | Sn1b—C1b | 2.20 (1) |
Sn1a—C5a | 2.13 (1) | Sn1b—C5b | 2.15 (1) |
Sn1a—C9a | 2.08 (1) | Sn1b—C9b | 2.14 (1) |
Sn1a—O1a | 2.285 (4) | Sn1b—O1b | 2.286 (5) |
Sn1a—O3ai | 2.292 (4) | Sn1b—O3bii | 2.292 (5) |
| | | |
C1a—Sn1a—C5a | 118.2 (4) | C1b—Sn1b—C5b | 115.6 (5) |
C1a—Sn1a—C9a | 117.0 (5) | C1b—Sn1b—C9b | 119.1 (5) |
C1a—Sn1a—O1a | 86.5 (3) | C1b—Sn1b—O1b | 87.8 (4) |
C1a—Sn1a—O3ai | 91.4 (3) | C1b—Sn1b—O3bii | 88.6 (4) |
C5a—Sn1a—C9a | 124.8 (5) | C5b—Sn1b—C9b | 125.3 (4) |
C5a—Sn1a—O1a | 91.6 (3) | C5b—Sn1b—O1b | 88.3 (3) |
C5a—Sn1a—O3ai | 94.0 (3) | C5b—Sn1b—O3bii | 94.9 (3) |
C9a—Sn1a—O1a | 89.8 (3) | C9b—Sn1b—O1b | 93.8 (3) |
C9a—Sn1a—O3ai | 86.5 (3) | C9b—Sn1b—O3bii | 86.2 (3) |
O1a—Sn1a—O3ai | 174.3 (2) | O1b—Sn1b—O3bii | 176.0 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
Selected geometric parameters (Å, º) for (II) topSn1—C1 | 2.146 (5) | Sn1—O1 | 2.275 (2) |
Sn1—C5 | 2.152 (4) | Sn1—O3i | 2.279 (2) |
Sn1—C9 | 2.113 (5) | | |
| | | |
C1—Sn1—C5 | 115.3 (2) | C5—Sn1—O1 | 91.9 (1) |
C1—Sn1—C9 | 124.2 (2) | C5—Sn1—O3i | 85.3 (1) |
C1—Sn1—O1 | 87.0 (1) | C9—Sn1—O1 | 92.3 (2) |
C1—Sn1—O3i | 90.2 (2) | C9—Sn1—O3i | 93.0 (2) |
C5—Sn1—C9 | 120.5 (2) | O1—Sn1—O3i | 174.7 (1) |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
Among the triorganotin derivatives of polycarboxylic acids, the ammonium triorganotin dicarboxylates represent a class of stannates whose biological properties are expected to be improved compared with those of neutral triorganotin monocarboxylates or bis(triorganotin) dicarboxylates because of the potentially greater degree of aqueous solubility. Dicyclohexylammonium tributyltin pyridine-2,6-dicarboxylate exists as a linear hydrogen-bonded polyanionic chain motif; the ammonium counterions surround the chain and they interact with the double-bond carbonyl oxygen atoms through hydrogen bonds [N···O = 2.75, 2.79 Å] (Ng, Kumar Das & Tiekink et al., 1991). The replacement of the pyridyl unit by the 4-oxo-4H-pyranyl entity results in the formation of a similar hydrogen-bonded architecture for dicyclohexylammonium 4-oxo-4H-pyran-2,6-dicarboxylatotributylstannate, (I), which crystallizes as two symmetry-independent hydrogen-bonded chains. These are approximately related by (0.5 + x, y, 0.45 − z), such a relationship suggesting the possibility of a stacking fault. The tin atoms show trans-C3SnO2 trigonal bipyramidal coordination [chain a: Sn—O = 2.285 (4), 2.292 (4) Å, O—Sn—O = 174.3 (2)°; chain b: Sn—O = 2.286 (5), 2.292 (5) Å, O—Sn—O = 176.0 (2)°]; the negatively-charged carboxyl oxygen atoms of the dicarboxylato dianion binds to two adjacent tributyltin cations. The tin-oxygen bond distances are longer than covalent tin-oxygen bonds but shorter than dative tin-oxygen bonds found in most triorganotin carboxylates (Tiekink, 1991, 1994). The bond distances are somewhat longer than those [Sn—O = 2.26 (1), 2.31 (1) Å] found in poly(dicyclohexylammonium 2,6-pyridinedicarboxylatotributylstannate) (Ng, Kumar Das & Tiekink et al., 1991) and that [Sn—O = 2.214 (2) Å] found in poly(dicyclohexylammonium succinatotriphenylstannate) (Ng, Kumar Das, Xiao et al., 1991); in (I), the tin atom lies on a special position so that the two tin-oxygen bonds are equivalent. \sch
The connectivity between the dianionic and cationic groups leads to the formation of a polyanionic zigzag chain structure. The sec-ammonium cations surround the chain, and each cation forms a pair of hydrogen bonds [chain a: N···O = 2.785 (7), 2.788 (7) Å; chain b: N···O = 2.765 (7), 2.786 (8) Å]. The ketonic oxygen atom of the 4-oxo-4H-pyran moiety is not involved in hydrogen bonding.
Whereas poly(2,6-pyridinedicarboxylatotributylstannate) adopts a zigzag chain motif in the dicyclohexylammonium derivative (Ng, Kumar Das & Tiekink et al., 1991), the polyanion in methylphenylammonium pyridine-2,6-dicarboxylatotributylstannate, (II), adopts a linear arrangement that is neither zigzag or helical as the chain propagates on the a-c face of the monoclinic cell. The repeat distance of (II) is half the a-c diagonal (a/c = 11.10 Å); this distance is nearly identical to that (c/2 = 11.06 Å) of the dicyclohexylammonium derivative. The similarity of the two repeat distances suggests that the nature of the ammonium counterion governs packing. However, the packing of both compounds appears to be inefficient, as noted from the accessible voids. In (II), there are two such voids of 37.6 Å3 in the unit cell. The hydrogen bonds in (II) [N···O = 2.732 (5), 2.763 (4) Å] are much shorter than that [N···O = 2.904 (3) Å] found in the methylphenylammonium hydrogen 2,6-pyridinedicarboxylate (Ng & Turnbull, 1998) reactant.