The six-coordinate Sn atom in bis(diisopropylammonium) dimethyldioxalatostannate, [(C3H7)2NH2]2+ [(CH3)2Sn(O2CCO2)]2-, exists in a cis-C2SnO4 coordination sphere [Sn-C 2.127 (5) Å; C-Sn-C 109.2 (3)°]. The anion lies on a special position of 2 symmetry. The ammonium cations and the stannate anions are linked by hydrogen bonds into a linear chain.
Supporting information
CCDC reference: 225659
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.041
- wR factor = 0.098
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.18 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Sn1
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C7
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C2 - C3 = 1.55 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C6 H16 N
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(diisopropylammonium) dimethyldioxalatostannate
top
Crystal data top
[Sn(C6H8O8)2]2C6H16N | F(000) = 1096 |
Mr = 529.19 | Dx = 1.387 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.4714 (8) Å | Cell parameters from 5928 reflections |
b = 14.0769 (7) Å | θ = 2.5–27.6° |
c = 11.0443 (5) Å | µ = 1.05 mm−1 |
β = 98.128 (1)° | T = 298 K |
V = 2535.1 (2) Å3 | Parallelelpiped, colorless |
Z = 4 | 0.47 × 0.40 × 0.09 mm |
Data collection top
Bruker APEX area-detector diffractometer | 2234 independent reflections |
Radiation source: fine-focus sealed tube | 2062 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scan | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.652, Tmax = 0.910 | k = −16→16 |
8978 measured reflections | l = −13→13 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3 |
2234 reflections | (Δ/σ)max = 0.001 |
133 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.5000 | 0.34503 (2) | 0.7500 | 0.0463 (2) | |
O1 | 0.5191 (1) | 0.2258 (2) | 0.8775 (2) | 0.0516 (6) | |
O2 | 0.4604 (2) | 0.1542 (2) | 1.0228 (3) | 0.0610 (8) | |
O3 | 0.3817 (2) | 0.3179 (2) | 0.8008 (2) | 0.0543 (7) | |
O4 | 0.3138 (2) | 0.2304 (2) | 0.9185 (2) | 0.0637 (8) | |
N1 | 0.3279 (2) | 0.1588 (2) | 1.1708 (3) | 0.0454 (7) | |
C1 | 0.5566 (3) | 0.4325 (4) | 0.8948 (5) | 0.087 (2) | |
C2 | 0.4591 (2) | 0.2054 (3) | 0.9334 (3) | 0.044 (1) | |
C3 | 0.3770 (2) | 0.2537 (3) | 0.8811 (3) | 0.045 (1) | |
C4 | 0.3674 (2) | 0.2136 (3) | 1.2792 (3) | 0.056 (1) | |
C5 | 0.3824 (3) | 0.3126 (4) | 1.2363 (5) | 0.083 (2) | |
C6 | 0.3132 (3) | 0.2153 (4) | 1.3799 (4) | 0.084 (2) | |
C7 | 0.3056 (3) | 0.0568 (3) | 1.1890 (4) | 0.063 (1) | |
C8 | 0.3812 (4) | −0.0006 (4) | 1.2341 (7) | 0.114 (2) | |
C9 | 0.2604 (3) | 0.0212 (3) | 1.0694 (5) | 0.092 (2) | |
H1n1 | 0.3620 | 0.1604 | 1.1138 | 0.054* | |
H1n2 | 0.2819 | 0.1898 | 1.1395 | 0.054* | |
H1a | 0.5422 | 0.4976 | 0.8775 | 0.130* | |
H1b | 0.6151 | 0.4254 | 0.9024 | 0.130* | |
H1C | 0.5382 | 0.4139 | 0.9700 | 0.130* | |
H4 | 0.4200 | 0.1841 | 1.3107 | 0.069* | |
H5a | 0.3903 | 0.3548 | 1.3052 | 0.125* | |
H5b | 0.3360 | 0.3333 | 1.1799 | 0.125* | |
H5c | 0.4305 | 0.3130 | 1.1963 | 0.125* | |
H6a | 0.3402 | 0.2501 | 1.4488 | 0.126* | |
H6b | 0.3033 | 0.1514 | 1.4044 | 0.126* | |
H6c | 0.2620 | 0.2454 | 1.3500 | 0.126* | |
H7 | 0.2684 | 0.0542 | 1.2508 | 0.076* | |
H8a | 0.3657 | −0.0572 | 1.2735 | 0.172* | |
H8b | 0.4174 | 0.0365 | 1.2914 | 0.172* | |
H8c | 0.4087 | −0.0175 | 1.1661 | 0.172* | |
H9a | 0.2282 | −0.0333 | 1.0841 | 0.137* | |
H9b | 0.2993 | 0.0038 | 1.0161 | 0.137* | |
H9c | 0.2251 | 0.0703 | 1.0317 | 0.137* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0382 (2) | 0.0567 (3) | 0.0465 (2) | 0.000 | 0.0146 (2) | 0.000 |
O1 | 0.033 (1) | 0.072 (2) | 0.051 (2) | 0.010 (1) | 0.011 (1) | 0.009 (1) |
O2 | 0.049 (2) | 0.080 (2) | 0.054 (2) | 0.007 (1) | 0.006 (1) | 0.020 (1) |
O3 | 0.035 (1) | 0.075 (2) | 0.055 (2) | 0.012 (1) | 0.014 (1) | 0.019 (1) |
O4 | 0.035 (1) | 0.101 (2) | 0.058 (2) | 0.005 (1) | 0.014 (1) | 0.024 (2) |
N1 | 0.037 (2) | 0.057 (2) | 0.042 (2) | 0.000 (1) | 0.007 (1) | 0.010 (1) |
C1 | 0.098 (4) | 0.083 (4) | 0.083 (3) | −0.016 (3) | 0.025 (3) | −0.038 (3) |
C2 | 0.038 (2) | 0.055 (2) | 0.039 (2) | 0.000 (2) | 0.004 (2) | −0.001 (2) |
C3 | 0.034 (2) | 0.065 (2) | 0.038 (2) | 0.005 (2) | 0.007 (1) | 0.000 (2) |
C4 | 0.041 (2) | 0.081 (3) | 0.048 (2) | −0.005 (2) | −0.005 (2) | 0.001 (2) |
C5 | 0.079 (3) | 0.085 (3) | 0.085 (3) | −0.035 (3) | 0.012 (3) | −0.016 (3) |
C6 | 0.084 (3) | 0.122 (5) | 0.047 (2) | −0.021 (3) | 0.014 (2) | −0.009 (3) |
C7 | 0.061 (3) | 0.058 (3) | 0.072 (3) | −0.006 (2) | 0.016 (2) | 0.017 (2) |
C8 | 0.114 (5) | 0.079 (4) | 0.148 (6) | 0.021 (3) | 0.011 (4) | 0.043 (4) |
C9 | 0.110 (4) | 0.061 (3) | 0.103 (4) | −0.022 (3) | 0.014 (3) | −0.014 (3) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.127 (5) | N1—H1n2 | 0.90 |
Sn1—C1i | 2.127 (5) | C1—H1a | 0.96 |
Sn1—O3 | 2.138 (2) | C1—H1b | 0.96 |
Sn1—O3i | 2.138 (2) | C1—H1c | 0.96 |
Sn1—O1 | 2.185 (3) | C4—H4 | 0.98 |
Sn1—O1i | 2.185 (3) | C5—H5a | 0.96 |
O1—C2 | 1.269 (4) | C5—H5b | 0.96 |
O2—C2 | 1.220 (4) | C5—H5c | 0.96 |
O3—C3 | 1.276 (4) | C6—H6a | 0.96 |
O4—C3 | 1.218 (4) | C6—H6b | 0.96 |
N1—C4 | 1.494 (5) | C6—H6c | 0.96 |
N1—C7 | 1.503 (5) | C7—H7 | 0.98 |
C2—C3 | 1.551 (5) | C8—H8a | 0.96 |
C4—C5 | 1.504 (6) | C8—H8b | 0.96 |
C4—C6 | 1.521 (6) | C8—H8c | 0.96 |
C7—C9 | 1.508 (6) | C9—H9a | 0.96 |
C7—C8 | 1.509 (7) | C9—H9b | 0.96 |
N1—H1n1 | 0.90 | C9—H9c | 0.96 |
| | | |
C1—Sn1—C1i | 109.2 (3) | Sn1—C1—H1b | 109.5 |
C1—Sn1—O1 | 87.3 (2) | H1a—C1—H1b | 109.5 |
C1—Sn1—O1i | 159.6 (2) | Sn1—C1—H1c | 109.5 |
C1—Sn1—O3 | 103.0 (2) | H1a—C1—H1c | 109.5 |
C1—Sn1—O3i | 89.0 (2) | H1b—C1—H1c | 109.5 |
C1i—Sn1—O1 | 159.6 (2) | N1—C4—H4 | 109.2 |
C1i—Sn1—O3 | 89.0 (2) | C5—C4—H4 | 109.2 |
C1i—Sn1—O1i | 87.3 (2) | C6—C4—H4 | 109.2 |
C1i—Sn1—O3i | 103.0 (2) | C4—C5—H5a | 109.5 |
O1—Sn1—O1i | 79.6 (1) | C4—C5—H5b | 109.5 |
O1—Sn1—O3 | 75.3 (1) | H5a—C5—H5b | 109.5 |
O1—Sn1—O3i | 88.8 (1) | C4—C5—H5c | 109.5 |
O1i—Sn1—O3 | 88.8 (1) | H5a—C5—H5c | 109.5 |
O1i—Sn1—O3i | 75.3 (1) | H5b—C5—H5c | 109.5 |
O3—Sn1—O3i | 159.4 (2) | C4—C6—H6a | 109.5 |
C2—O1—Sn1 | 115.9 (2) | C4—C6—H6b | 109.5 |
C3—O3—Sn1 | 117.1 (2) | H6a—C6—H6b | 109.5 |
C4—N1—C7 | 118.2 (3) | C4—C6—H6c | 109.5 |
O2—C2—O1 | 127.0 (3) | H6a—C6—H6c | 109.5 |
O2—C2—C3 | 118.3 (3) | H6b—C6—H6c | 109.5 |
O1—C2—C3 | 114.7 (3) | N1—C7—H7 | 108.6 |
O4—C3—O3 | 124.4 (3) | C9—C7—H7 | 108.6 |
O4—C3—C2 | 119.9 (3) | C8—C7—H7 | 108.6 |
O3—C3—C2 | 115.7 (3) | C7—C8—H8a | 109.5 |
N1—C4—C5 | 107.3 (3) | C7—C8—H8b | 109.5 |
N1—C4—C6 | 111.1 (3) | H8a—C8—H8b | 109.5 |
C5—C4—C6 | 110.9 (4) | C7—C8—H8c | 109.5 |
N1—C7—C9 | 107.5 (3) | H8a—C8—H8c | 109.5 |
N1—C7—C8 | 110.5 (4) | H8b—C8—H8c | 109.5 |
C9—C7—C8 | 113.2 (5) | C7—C9—H9a | 109.5 |
C4—N1—H1n1 | 107.8 | C7—C9—H9b | 109.5 |
C7—N1—H1n1 | 107.8 | H9a—C9—H9b | 109.5 |
C4—N1—H1n2 | 107.8 | C7—C9—H9c | 109.5 |
C7—N1—H1n2 | 107.8 | H9a—C9—H9c | 109.5 |
H1n1—N1—H1n2 | 107.1 | H9b—C9—H9c | 109.5 |
Sn1—C1—H1a | 109.5 | | |
| | | |
C1—Sn1—O1—C2 | 94.8 (3) | Sn1—O1—C2—C3 | 12.8 (4) |
C1i—Sn1—O1—C2 | −50.1 (5) | Sn1—O3—C3—O4 | −179.6 (3) |
O3—Sn1—O1—C2 | −9.4 (2) | Sn1—O3—C3—C2 | 1.4 (4) |
O3i—Sn1—O1—C2 | −176.2 (2) | O2—C2—C3—O4 | −9.9 (5) |
O1i—Sn1—O1—C2 | −100.9 (3) | O1—C2—C3—O4 | 171.3 (3) |
C1—Sn1—O3—C3 | −79.9 (3) | O2—C2—C3—O3 | 169.2 (3) |
C1i—Sn1—O3—C3 | 170.6 (3) | O1—C2—C3—O3 | −9.7 (5) |
O3i—Sn1—O3—C3 | 44.3 (3) | C7—N1—C4—C5 | −179.5 (4) |
O1—Sn1—O3—C3 | 3.7 (3) | C7—N1—C4—C6 | −58.1 (5) |
O1i—Sn1—O3—C3 | 83.3 (3) | C4—N1—C7—C9 | 175.0 (4) |
Sn1—O1—C2—O2 | −166.0 (3) | C4—N1—C7—C8 | −61.2 (5) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O2 | 0.90 | 2.03 | 2.906 (4) | 165 |
N1—H1n1···O4 | 0.90 | 2.40 | 2.941 (4) | 119 |
N1—H1n2···O4ii | 0.90 | 1.97 | 2.864 (4) | 174 |
Symmetry code: (ii) −x+1/2, −y+1/2, −z+2. |