Synthesis, structure determination and characterization by UV–Vis and IR spectroscopy of bis­(diiso­propyl­ammonium) cis-di­chlorido­bis(oxalato-κ²O¹,O²)stannate(IV)

In the crystal structure of the title compound, (C₆H₁₆N)₂[Sn(C₂O₄)₂Cl₂], the cations are linked to the anions by N—H...O hydrogen bonds to generate chains along the c-axis direction. Only van der Waals inter­actions are observed between the chains.

checkCIF/PLATON results

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Datablock: I


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3       --C8       .        5.1 s.u.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.19 Why ?
PLAT794_ALERT_5_G Tentative Bond Valency for Sn1       (IV)      .       4.11 Info
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(diisopropylammonium) cis-dichloridobis(oxalato-κ²O¹,O²)stannate(IV)

Crystal data

(C6H16N)2[Sn(C2ClO4)2]	F(000) = 1160
Mr = 570.02	Dx = 1.558 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.275 (8) Å	Cell parameters from 7290 reflections
b = 13.581 (6) Å	θ = 3.0–27.5°
c = 11.116 (4) Å	µ = 1.31 mm^−1
β = 98.40 (3)°	T = 100 K
V = 2430.7 (18) Å^3	Plate, clear light colourless
Z = 4	0.56 × 0.30 × 0.22 mm

Data collection

Bruker D8 VENTURE diffractometer	2800 independent reflections
Radiation source: X-ray tube, Siemens KFF Mo 2K-90C	2597 reflections with I > 2σ(I)
TRIUMPH curved crystal monochromator	Rint = 0.023
Detector resolution: 1024 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans'	h = −20→21
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −17→17
Tmin = 0.626, Tmax = 0.746	l = −14→14
14360 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.011P)^2 + 6.1885P] where P = (Fo^2 + 2Fc^2)/3
S = 1.28	(Δ/σ)max = 0.002
2800 reflections	Δρmax = 1.01 e Å^−3
136 parameters	Δρmin = −0.59 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.5000	0.67465 (2)	0.7500	0.01307 (6)
Cl1	0.55290 (4)	0.56066 (4)	0.89962 (5)	0.02556 (12)
O1	0.38232 (9)	0.69379 (11)	0.79635 (12)	0.0158 (3)
O2	0.31479 (8)	0.77413 (11)	0.92602 (12)	0.0165 (3)
O3	0.46345 (9)	0.85537 (11)	1.03026 (12)	0.0159 (3)
O4	0.52285 (9)	0.78744 (10)	0.88059 (12)	0.0147 (3)
C7	0.37835 (11)	0.75429 (14)	0.88463 (16)	0.0117 (3)
C8	0.46144 (11)	0.80483 (14)	0.93878 (17)	0.0121 (4)
N1	0.82801 (10)	0.66470 (12)	0.67738 (14)	0.0117 (3)
H1A	0.8640	0.6618	0.6220	0.014*
H1B	0.7824	0.6983	0.6421	0.014*
C1	0.80130 (13)	0.56088 (15)	0.70045 (19)	0.0180 (4)
H1	0.7608	0.5626	0.7599	0.022*
C2	0.87571 (16)	0.49960 (18)	0.7530 (2)	0.0317 (6)
H2A	0.8580	0.4317	0.7643	0.048*
H2B	0.9003	0.5271	0.8316	0.048*
H2C	0.9170	0.5004	0.6970	0.048*
C3	0.75809 (16)	0.52045 (17)	0.5802 (2)	0.0268 (5)
H3A	0.7113	0.5632	0.5490	0.040*
H3B	0.7376	0.4539	0.5926	0.040*
H3C	0.7975	0.5181	0.5215	0.040*
C4	0.86854 (12)	0.72450 (16)	0.78415 (18)	0.0163 (4)
H4	0.9228	0.6934	0.8176	0.020*
C5	0.88477 (14)	0.82664 (16)	0.7363 (2)	0.0225 (4)
H5A	0.9179	0.8209	0.6698	0.034*
H5B	0.9151	0.8662	0.8020	0.034*
H5C	0.8317	0.8586	0.7063	0.034*
C6	0.81368 (14)	0.72851 (18)	0.88350 (19)	0.0231 (5)
H6A	0.7582	0.7518	0.8491	0.035*
H6B	0.8380	0.7738	0.9476	0.035*
H6C	0.8094	0.6626	0.9179	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01120 (10)	0.01596 (10)	0.01279 (10)	0.000	0.00420 (6)	0.000
Cl1	0.0335 (3)	0.0221 (3)	0.0217 (2)	0.0028 (2)	0.0062 (2)	0.0098 (2)
O1	0.0111 (6)	0.0235 (7)	0.0134 (6)	−0.0049 (6)	0.0037 (5)	−0.0063 (6)
O2	0.0099 (6)	0.0262 (8)	0.0139 (7)	−0.0022 (6)	0.0035 (5)	−0.0046 (6)
O3	0.0147 (7)	0.0193 (7)	0.0130 (6)	−0.0013 (6)	0.0001 (5)	−0.0048 (5)
O4	0.0138 (7)	0.0166 (7)	0.0146 (7)	−0.0011 (5)	0.0056 (5)	−0.0016 (5)
C7	0.0112 (8)	0.0143 (9)	0.0095 (8)	−0.0013 (7)	0.0009 (7)	0.0026 (7)
C8	0.0088 (8)	0.0143 (9)	0.0125 (8)	−0.0005 (7)	−0.0008 (7)	0.0032 (7)
N1	0.0115 (7)	0.0134 (8)	0.0100 (7)	0.0003 (6)	0.0013 (6)	0.0021 (6)
C1	0.0200 (10)	0.0132 (9)	0.0211 (10)	−0.0016 (8)	0.0040 (8)	0.0049 (8)
C2	0.0323 (13)	0.0207 (11)	0.0403 (14)	0.0066 (10)	−0.0010 (11)	0.0129 (10)
C3	0.0327 (13)	0.0165 (10)	0.0312 (12)	−0.0058 (9)	0.0042 (10)	−0.0029 (9)
C4	0.0118 (9)	0.0227 (10)	0.0131 (9)	−0.0002 (8)	−0.0030 (7)	−0.0018 (8)
C5	0.0213 (11)	0.0208 (10)	0.0246 (11)	−0.0058 (9)	0.0006 (8)	−0.0019 (9)
C6	0.0250 (11)	0.0294 (12)	0.0144 (10)	0.0001 (9)	0.0016 (8)	−0.0015 (8)

Geometric parameters (Å, º)

Sn1—Cl1	2.3422 (9)	C1—C3	1.519 (3)
Sn1—Cl1^i	2.3422 (9)	C2—H2A	0.9800
Sn1—O1	2.0710 (16)	C2—H2B	0.9800
Sn1—O1^i	2.0711 (16)	C2—H2C	0.9800
Sn1—O4^i	2.1057 (15)	C3—H3A	0.9800
Sn1—O4	2.1058 (15)	C3—H3B	0.9800
O1—C7	1.289 (2)	C3—H3C	0.9800
O2—C7	1.222 (2)	C4—H4	1.0000
O3—C8	1.223 (2)	C4—C5	1.523 (3)
O4—C8	1.289 (2)	C4—C6	1.519 (3)
C7—C8	1.557 (3)	C5—H5A	0.9800
N1—H1A	0.9100	C5—H5B	0.9800
N1—H1B	0.9100	C5—H5C	0.9800
N1—C1	1.508 (3)	C6—H6A	0.9800
N1—C4	1.508 (2)	C6—H6B	0.9800
C1—H1	1.0000	C6—H6C	0.9800
C1—C2	1.514 (3)
Cl1^i—Sn1—Cl1	97.26 (4)	C2—C1—C3	112.4 (2)
O1—Sn1—Cl1	99.42 (5)	C3—C1—H1	109.0
O1—Sn1—Cl1^i	90.13 (5)	C1—C2—H2A	109.5
O1^i—Sn1—Cl1	90.13 (5)	C1—C2—H2B	109.5
O1^i—Sn1—Cl1^i	99.42 (5)	C1—C2—H2C	109.5
O1—Sn1—O1^i	165.59 (8)	H2A—C2—H2B	109.5
O1—Sn1—O4	79.27 (6)	H2A—C2—H2C	109.5
O1—Sn1—O4^i	90.21 (6)	H2B—C2—H2C	109.5
O1^i—Sn1—O4^i	79.27 (6)	C1—C3—H3A	109.5
O1^i—Sn1—O4	90.21 (6)	C1—C3—H3B	109.5
O4^i—Sn1—Cl1	168.50 (4)	C1—C3—H3C	109.5
O4—Sn1—Cl1^i	168.49 (4)	H3A—C3—H3B	109.5
O4^i—Sn1—Cl1^i	88.95 (5)	H3A—C3—H3C	109.5
O4—Sn1—Cl1	88.95 (5)	H3B—C3—H3C	109.5
O4^i—Sn1—O4	86.66 (8)	N1—C4—H4	109.0
C7—O1—Sn1	114.87 (12)	N1—C4—C5	107.09 (16)
C8—O4—Sn1	114.04 (12)	N1—C4—C6	110.83 (17)
O1—C7—C8	115.98 (16)	C5—C4—H4	109.0
O2—C7—O1	124.51 (18)	C6—C4—H4	109.0
O2—C7—C8	119.50 (17)	C6—C4—C5	111.83 (18)
O3—C8—O4	126.25 (18)	C4—C5—H5A	109.5
O3—C8—C7	119.01 (17)	C4—C5—H5B	109.5
O4—C8—C7	114.74 (16)	C4—C5—H5C	109.5
H1A—N1—H1B	107.1	H5A—C5—H5B	109.5
C1—N1—H1A	107.7	H5A—C5—H5C	109.5
C1—N1—H1B	107.7	H5B—C5—H5C	109.5
C4—N1—H1A	107.7	C4—C6—H6A	109.5
C4—N1—H1B	107.7	C4—C6—H6B	109.5
C4—N1—C1	118.25 (15)	C4—C6—H6C	109.5
N1—C1—H1	109.0	H6A—C6—H6B	109.5
N1—C1—C2	110.20 (18)	H6A—C6—H6C	109.5
N1—C1—C3	107.23 (16)	H6B—C6—H6C	109.5
C2—C1—H1	109.0
Sn1—O1—C7—O2	−178.95 (15)	O2—C7—C8—O3	7.8 (3)
Sn1—O1—C7—C8	1.7 (2)	O2—C7—C8—O4	−172.75 (17)
Sn1—O4—C8—O3	168.18 (16)	C1—N1—C4—C5	−177.16 (17)
Sn1—O4—C8—C7	−11.23 (19)	C1—N1—C4—C6	−54.9 (2)
O1—C7—C8—O3	−172.83 (17)	C4—N1—C1—C2	−60.8 (2)
O1—C7—C8—O4	6.6 (2)	C4—N1—C1—C3	176.56 (17)

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—H1A···O3^ii	0.91	2.05	2.943 (2)	167
N1—H1B···O2^i	0.91	1.95	2.855 (2)	177

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x+1/2, −y+3/2, z−1/2.