Bis­(diiso­propyl­ammonium) di­methyl­dioxalatostannate

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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

Crystal data

[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) Å^3	Parallelelpiped, colorless
Z = 4	0.47 × 0.40 × 0.09 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0578P)^2] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Sn1—C1	2.127 (5)	N1—H1n2	0.90
Sn1—C1^i	2.127 (5)	C1—H1a	0.96
Sn1—O3	2.138 (2)	C1—H1b	0.96
Sn1—O3^i	2.138 (2)	C1—H1c	0.96
Sn1—O1	2.185 (3)	C4—H4	0.98
Sn1—O1^i	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—C1^i	109.2 (3)	Sn1—C1—H1b	109.5
C1—Sn1—O1	87.3 (2)	H1a—C1—H1b	109.5
C1—Sn1—O1^i	159.6 (2)	Sn1—C1—H1c	109.5
C1—Sn1—O3	103.0 (2)	H1a—C1—H1c	109.5
C1—Sn1—O3^i	89.0 (2)	H1b—C1—H1c	109.5
C1^i—Sn1—O1	159.6 (2)	N1—C4—H4	109.2
C1^i—Sn1—O3	89.0 (2)	C5—C4—H4	109.2
C1^i—Sn1—O1^i	87.3 (2)	C6—C4—H4	109.2
C1^i—Sn1—O3^i	103.0 (2)	C4—C5—H5a	109.5
O1—Sn1—O1^i	79.6 (1)	C4—C5—H5b	109.5
O1—Sn1—O3	75.3 (1)	H5a—C5—H5b	109.5
O1—Sn1—O3^i	88.8 (1)	C4—C5—H5c	109.5
O1^i—Sn1—O3	88.8 (1)	H5a—C5—H5c	109.5
O1^i—Sn1—O3^i	75.3 (1)	H5b—C5—H5c	109.5
O3—Sn1—O3^i	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)
C1^i—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)
O3^i—Sn1—O1—C2	−176.2 (2)	O2—C2—C3—O4	−9.9 (5)
O1^i—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)
C1^i—Sn1—O3—C3	170.6 (3)	O1—C2—C3—O3	−9.7 (5)
O3^i—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)
O1^i—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)

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···O4^ii	0.90	1.97	2.864 (4)	174

Symmetry code: (ii) −x+1/2, −y+1/2, −z+2.