The component species in the title compound, 2C
4H
12N
2+·C
2O
42−, interact by way of N—H
O hydrogen bonds, resulting in a layered network. N and two C atoms of the cation possess site symmetry
m and the C atom of the anion has site symmetry 2.
Supporting information
CCDC reference: 611212
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.107
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.08 Ratio
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C5 - C5_b ... 1.55 Ang.
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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
Bis(
tert-butylammonium) oxalate
top
Crystal data top
2C4H12N+·C2O42− | F(000) = 260 |
Mr = 236.31 | Dx = 1.072 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 2385 reflections |
a = 11.264 (2) Å | θ = 3.6–25.5° |
b = 7.512 (1) Å | µ = 0.08 mm−1 |
c = 9.324 (1) Å | T = 298 K |
β = 111.91 (1)° | Irregular, colourless |
V = 731.97 (19) Å3 | 0.50 × 0.48 × 0.45 mm |
Z = 2 | |
Data collection top
Oxford Diffraction Xcalibur diffractometer | 626 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 25.5°, θmin = 3.6° |
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1 | h = −13→13 |
ω scans | k = −9→7 |
2385 measured reflections | l = −11→11 |
731 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.1997P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
731 reflections | Δρmax = 0.17 e Å−3 |
50 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.069 (10) |
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 | |
N1 | 0.29155 (13) | 0.0000 | 0.90612 (16) | 0.0390 (4) | |
H1A | 0.3403 (12) | 0.1041 (19) | 0.9504 (15) | 0.053 (4)* | |
H1B | 0.224 (2) | 0.0000 | 0.926 (2) | 0.048 (5)* | |
C2 | 0.25685 (17) | 0.0000 | 0.7348 (2) | 0.0547 (5) | |
C3 | 0.3805 (2) | 0.0000 | 0.7049 (3) | 0.0676 (6) | |
H3A | 0.4315 | 0.1005 | 0.7550 | 0.101* | |
H3B | 0.3610 | 0.0000 | 0.5958 | 0.101* | |
C4 | 0.18000 (19) | 0.1678 (3) | 0.6707 (2) | 0.0985 (7) | |
H4A | 0.1020 | 0.1647 | 0.6900 | 0.148* | |
H4B | 0.1602 | 0.1744 | 0.5614 | 0.148* | |
H4C | 0.2292 | 0.2702 | 0.7203 | 0.148* | |
C5 | 0.0000 | 0.10342 (19) | 1.0000 | 0.0406 (4) | |
O6 | 0.08946 (9) | 0.17774 (10) | 0.97680 (13) | 0.0625 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0349 (7) | 0.0321 (7) | 0.0547 (9) | 0.000 | 0.0221 (6) | 0.000 |
C2 | 0.0501 (10) | 0.0659 (12) | 0.0515 (10) | 0.000 | 0.0229 (8) | 0.000 |
C3 | 0.0685 (13) | 0.0786 (14) | 0.0694 (13) | 0.000 | 0.0417 (11) | 0.000 |
C4 | 0.0943 (13) | 0.1270 (18) | 0.0758 (11) | 0.0507 (12) | 0.0337 (10) | 0.0400 (11) |
C5 | 0.0382 (8) | 0.0266 (8) | 0.0630 (10) | 0.000 | 0.0258 (7) | 0.000 |
O6 | 0.0610 (6) | 0.0299 (5) | 0.1182 (9) | −0.0097 (4) | 0.0583 (6) | −0.0080 (4) |
Geometric parameters (Å, º) top
N1—C2 | 1.496 (2) | C4—H4A | 0.9600 |
N1—H1A | 0.956 (14) | C4—H4B | 0.9600 |
N1—H1B | 0.85 (2) | C4—H4C | 0.9600 |
C2—C3 | 1.518 (3) | C5—O6 | 1.240 (1) |
C2—C4 | 1.519 (2) | C5—O6i | 1.240 (1) |
C3—H3A | 0.9583 | C5—C5ii | 1.554 (3) |
C3—H3B | 0.9570 | | |
| | | |
C2—N1—H1A | 109.9 (8) | C2—C3—H3B | 109.5 |
C2—N1—H1B | 109.7 (12) | H3A—C3—H3B | 112.1 |
H1A—N1—H1B | 108.8 (10) | C2—C4—H4A | 109.5 |
N1—C2—C3 | 107.69 (15) | C2—C4—H4B | 109.5 |
N1—C2—C4iii | 107.66 (11) | H4A—C4—H4B | 109.5 |
C3—C2—C4iii | 110.78 (12) | C2—C4—H4C | 109.5 |
N1—C2—C4 | 107.66 (11) | H4A—C4—H4C | 109.5 |
C3—C2—C4 | 110.78 (12) | H4B—C4—H4C | 109.5 |
C4iii—C2—C4 | 112.1 (2) | O6—C5—O6i | 126.5 (1) |
C2—C3—H3A | 109.5 | O6—C5—C5ii | 116.77 (7) |
Symmetry codes: (i) −x, y, −z+2; (ii) −x, −y, −z+2; (iii) x, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O6iv | 0.96 (1) | 1.84 (1) | 2.785 (1) | 171 (1) |
N1—H1B···O6 | 0.85 (2) | 2.20 (2) | 2.919 (2) | 143 (1) |
N1—H1B···O6iii | 0.85 (2) | 2.20 (2) | 2.919 (2) | 143 (1) |
Symmetry codes: (iii) x, −y, z; (iv) −x+1/2, −y+1/2, −z+2. |