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The title compound, (C7H8NO2)2[SnF6], has been prepared from 3-aminobenzoic acid and tin(II) fluoride in hydrofluoric acid. The structure can be described as alternating layers of SnF62- and C7H8NO2+ ions along the a axis, with the SnF62- ions lying on a twofold axis. The cations and anions are linked to each other through strong hydrogen bonds formed by all H atoms covalently bonded to the N and O atoms. This three-dimensional complex network of hydrogen bonds reinforces the cohesion of the ionic structure.
Supporting information
CCDC reference: 269368
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.027
- wR factor = 0.063
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997), PLATON (Spek, 2003)and ATOMS (Dowty, 1995); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
(C7H8NO2)2[SnF6] | F(000) = 1000 |
Mr = 508.98 | Dx = 1.958 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8090 reflections |
a = 22.2660 (5) Å | θ = 1.9–30.0° |
b = 10.6580 (5) Å | µ = 1.57 mm−1 |
c = 7.4920 (5) Å | T = 295 K |
β = 103.743 (5)° | Needles, brown |
V = 1727.03 (15) Å3 | 0.35 × 0.07 × 0.05 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 2291 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 30.0°, θmin = 1.9° |
φ scans, and ω scans with κ offsets | h = −23→31 |
8090 measured reflections | k = −14→12 |
2517 independent reflections | l = −10→10 |
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)] = 0.027 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.062P)2] where P = (Fo2 + 2Fc2)/3 |
2517 reflections | (Δ/σ)max = 0.001 |
145 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −1.11 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 1.0000 | 0.298590 (19) | 0.7500 | 0.02309 (7) | |
F4 | 1.0000 | 0.1171 (2) | 0.7500 | 0.0616 (7) | |
F3 | 1.01482 (7) | 0.30270 (15) | 0.50214 (19) | 0.0443 (4) | |
F2 | 0.91103 (6) | 0.30423 (15) | 0.6344 (2) | 0.0478 (4) | |
O2 | 0.67524 (7) | 0.03213 (17) | 0.1416 (2) | 0.0418 (4) | |
O1 | 0.69536 (8) | 0.21180 (16) | 0.2956 (3) | 0.0431 (5) | |
H1 | 0.6595 | 0.2036 | 0.3040 | 0.065* | |
N1 | 0.90569 (8) | 0.3503 (2) | 0.2348 (3) | 0.0291 (4) | |
C2 | 0.77497 (9) | 0.1239 (2) | 0.1801 (3) | 0.0250 (4) | |
C7 | 0.80055 (10) | 0.0180 (2) | 0.1198 (3) | 0.0318 (5) | |
C3 | 0.80964 (9) | 0.2338 (2) | 0.2206 (3) | 0.0249 (4) | |
C6 | 0.86128 (11) | 0.0201 (2) | 0.1038 (4) | 0.0379 (5) | |
C5 | 0.89611 (10) | 0.1287 (2) | 0.1426 (3) | 0.0335 (5) | |
F1 | 1.0000 | 0.4794 (2) | 0.7500 | 0.0577 (6) | |
C4 | 0.86947 (9) | 0.2344 (2) | 0.1984 (3) | 0.0239 (4) | |
C1 | 0.71029 (9) | 0.1174 (2) | 0.2027 (3) | 0.0284 (4) | |
H3 | 0.7935 (15) | 0.307 (3) | 0.262 (4) | 0.050* | |
H7 | 0.7782 (13) | −0.056 (3) | 0.096 (4) | 0.050* | |
H6 | 0.8793 (13) | −0.050 (3) | 0.065 (4) | 0.050* | |
H5 | 0.9366 (13) | 0.133 (3) | 0.131 (4) | 0.050* | |
H13 | 0.9219 (13) | 0.370 (3) | 0.143 (4) | 0.050* | |
H11 | 0.8840 (14) | 0.415 (3) | 0.262 (4) | 0.050* | |
H12 | 0.9345 (15) | 0.335 (3) | 0.326 (4) | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.01903 (10) | 0.02526 (12) | 0.02709 (11) | 0.000 | 0.00966 (7) | 0.000 |
F4 | 0.0677 (16) | 0.0251 (12) | 0.0931 (19) | 0.000 | 0.0211 (14) | 0.000 |
F3 | 0.0363 (8) | 0.0720 (12) | 0.0298 (7) | 0.0110 (7) | 0.0179 (6) | 0.0046 (6) |
F2 | 0.0168 (6) | 0.0829 (14) | 0.0438 (8) | 0.0000 (6) | 0.0076 (6) | −0.0016 (7) |
O2 | 0.0314 (8) | 0.0346 (10) | 0.0614 (11) | −0.0116 (7) | 0.0150 (8) | −0.0075 (8) |
O1 | 0.0259 (8) | 0.0404 (11) | 0.0687 (12) | −0.0080 (7) | 0.0225 (8) | −0.0175 (9) |
N1 | 0.0223 (9) | 0.0329 (11) | 0.0332 (10) | −0.0035 (8) | 0.0087 (7) | 0.0007 (8) |
C2 | 0.0227 (9) | 0.0258 (11) | 0.0269 (9) | −0.0021 (8) | 0.0069 (7) | 0.0016 (8) |
C7 | 0.0331 (11) | 0.0262 (12) | 0.0376 (11) | −0.0032 (9) | 0.0116 (9) | −0.0021 (9) |
C3 | 0.0229 (9) | 0.0249 (11) | 0.0279 (10) | 0.0016 (8) | 0.0080 (8) | 0.0003 (8) |
C6 | 0.0387 (12) | 0.0295 (13) | 0.0504 (14) | 0.0055 (10) | 0.0200 (11) | −0.0041 (11) |
C5 | 0.0259 (10) | 0.0358 (14) | 0.0424 (12) | 0.0030 (9) | 0.0153 (9) | 0.0008 (10) |
F1 | 0.0655 (15) | 0.0236 (12) | 0.0915 (18) | 0.000 | 0.0338 (14) | 0.000 |
C4 | 0.0217 (9) | 0.0258 (11) | 0.0249 (9) | −0.0029 (8) | 0.0069 (7) | 0.0021 (8) |
C1 | 0.0240 (9) | 0.0278 (12) | 0.0335 (10) | −0.0025 (8) | 0.0073 (8) | 0.0028 (9) |
Geometric parameters (Å, º) top
Sn1—F1 | 1.927 (2) | N1—H12 | 0.83 (3) |
Sn1—F4 | 1.934 (2) | C2—C7 | 1.387 (3) |
Sn1—F3i | 1.9622 (13) | C2—C3 | 1.396 (3) |
Sn1—F3 | 1.9622 (13) | C2—C1 | 1.491 (3) |
Sn1—F2 | 1.9654 (14) | C7—C6 | 1.386 (3) |
Sn1—F2i | 1.9654 (14) | C7—H7 | 0.93 (3) |
O2—C1 | 1.214 (3) | C3—C4 | 1.381 (3) |
O1—C1 | 1.311 (3) | C3—H3 | 0.94 (3) |
O1—H1 | 0.8200 | C6—C5 | 1.385 (3) |
N1—C4 | 1.466 (3) | C6—H6 | 0.93 (3) |
N1—H13 | 0.88 (3) | C5—C4 | 1.383 (3) |
N1—H11 | 0.89 (3) | C5—H5 | 0.93 (3) |
| | | |
F1—Sn1—F4 | 180.000 (1) | C7—C2—C3 | 120.31 (19) |
F1—Sn1—F3i | 88.72 (5) | C7—C2—C1 | 118.78 (19) |
F4—Sn1—F3i | 91.28 (5) | C3—C2—C1 | 120.90 (19) |
F1—Sn1—F3 | 88.72 (5) | C6—C7—C2 | 120.0 (2) |
F4—Sn1—F3 | 91.28 (5) | C6—C7—H7 | 119.1 (18) |
F3i—Sn1—F3 | 177.44 (9) | C2—C7—H7 | 120.9 (18) |
F1—Sn1—F2 | 88.25 (5) | C4—C3—C2 | 118.5 (2) |
F4—Sn1—F2 | 91.75 (5) | C4—C3—H3 | 119.2 (19) |
F3i—Sn1—F2 | 92.17 (6) | C2—C3—H3 | 122.3 (19) |
F3—Sn1—F2 | 87.75 (6) | C5—C6—C7 | 120.3 (2) |
F1—Sn1—F2i | 88.25 (5) | C5—C6—H6 | 118.5 (18) |
F4—Sn1—F2i | 91.75 (5) | C7—C6—H6 | 121.1 (18) |
F3i—Sn1—F2i | 87.75 (6) | C4—C5—C6 | 119.0 (2) |
F3—Sn1—F2i | 92.17 (6) | C4—C5—H5 | 119 (2) |
F2—Sn1—F2i | 176.50 (10) | C6—C5—H5 | 122 (2) |
C1—O1—H1 | 109.5 | C3—C4—C5 | 121.9 (2) |
C4—N1—H13 | 112 (2) | C3—C4—N1 | 119.0 (2) |
C4—N1—H11 | 113.0 (19) | C5—C4—N1 | 119.11 (19) |
H13—N1—H11 | 110 (3) | O2—C1—O1 | 123.59 (19) |
C4—N1—H12 | 106 (2) | O2—C1—C2 | 122.9 (2) |
H13—N1—H12 | 108 (3) | O1—C1—C2 | 113.46 (18) |
H11—N1—H12 | 108 (3) | | |
| | | |
C3—C2—C7—C6 | 1.6 (3) | C2—C3—C4—N1 | 178.08 (19) |
C1—C2—C7—C6 | −177.7 (2) | C6—C5—C4—C3 | 1.6 (3) |
C7—C2—C3—C4 | 0.3 (3) | C6—C5—C4—N1 | −178.4 (2) |
C1—C2—C3—C4 | 179.60 (19) | C7—C2—C1—O2 | −13.1 (3) |
C2—C7—C6—C5 | −1.9 (4) | C3—C2—C1—O2 | 167.6 (2) |
C7—C6—C5—C4 | 0.4 (4) | C7—C2—C1—O1 | 166.4 (2) |
C2—C3—C4—C5 | −1.9 (3) | C3—C2—C1—O1 | −12.9 (3) |
Symmetry code: (i) −x+2, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···F2ii | 0.82 | 1.74 | 2.551 (2) | 169 |
N1—H11···O2iii | 0.89 (3) | 2.07 (3) | 2.942 (3) | 166 (3) |
N1—H12···F2 | 0.83 (3) | 2.51 (3) | 3.008 (3) | 119 (3) |
N1—H12···F3 | 0.83 (3) | 1.98 (3) | 2.804 (3) | 167 (3) |
N1—H13···F3iv | 0.87 (3) | 2.10 (3) | 2.834 (3) | 141 (3) |
N1—H13···F1v | 0.87 (3) | 2.36 (3) | 2.757 (2) | 108 (2) |
C3—H3···O2iii | 0.94 (3) | 2.55 (3) | 3.335 (3) | 140 (3) |
C5—H5···F3iv | 0.93 (3) | 2.44 (3) | 3.094 (3) | 128 (2) |
Symmetry codes: (ii) −x+3/2, −y+1/2, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+2, y, −z+1/2; (v) −x+2, −y+1, −z+1. |
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