The title compound, C
14H
22N
2O
6, possesses
Ci symmetry and crystallizes with one half-molecule in the aymmetric unit. The structure can be described as cyclohexyldiamide singly bonded to two ethyl carboxylate groups. The supramolecular structure is achieved through intermolecular hard N—H
O hydrogen-bonding interactions involving only the amide group. The full hydrogen-bonding network is described by the
C22(8)[
S(5)
S(5)
C(4)] motif that develops along the c-axis direction.
Supporting information
CCDC reference: 283930
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.004 Å
- R factor = 0.073
- wR factor = 0.177
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.06 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.15
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C5 - C6 ... 1.54 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and WinGX2003 (Farrugia, 1999).
Diethyl
N,
N'-cyclohexane-1,4-diyldioxalamate
top
Crystal data top
| C14H22N2O6 | F(000) = 336 |
| Mr = 314.34 | Dx = 1.328 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 600 reflections |
| a = 13.145 (3) Å | θ = 20–25° |
| b = 7.2093 (15) Å | µ = 0.10 mm−1 |
| c = 8.6617 (17) Å | T = 100 K |
| β = 106.709 (3)° | Block, colorless |
| V = 786.2 (3) Å3 | 0.20 × 0.15 × 0.09 mm |
| Z = 2 | |
Data collection top
Bruker SMART area-detector
diffractometer | Rint = 0.030 |
| Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
| φ and ω scans | h = −16→16 |
| 7841 measured reflections | k = −8→8 |
| 1546 independent reflections | l = −10→10 |
| 1387 reflections with I > 2σ(I) | |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.177 | H-atom parameters constrained |
| S = 1.19 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.4735P]
where P = (Fo2 + 2Fc2)/3 |
| 1546 reflections | (Δ/σ)max < 0.001 |
| 101 parameters | Δρmax = 0.26 e Å−3 |
| 0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
Experimental. The melting point was measured on an Electrothermal IA 9100 apparatus and is
uncorrected. IR spectra were recorded neat on a Perkin-Elmer FT—IR
Spectrum-GX equipped with an ATR device. 1H and 13C NMR spectra
were recorded on a Varian Mercury 300 (1H, 300.08; 13C, 75.46 MHz)
equipment in [2H6]DMSO solution, measured with SiMe4 as internal
reference following standard techniques. |
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | |
| O5 | 0.19907 (15) | 0.4483 (3) | −0.02520 (19) | 0.0476 (6) | |
| O6 | 0.32182 (19) | 0.4100 (3) | 0.3876 (2) | 0.0741 (8) | |
| O7 | 0.32815 (15) | 0.6378 (3) | 0.2178 (2) | 0.0492 (6) | |
| N4 | 0.17444 (15) | 0.2328 (3) | 0.1509 (2) | 0.0406 (6) | |
| C1 | 0.08982 (19) | 0.1291 (3) | 0.0385 (3) | 0.0392 (7) | |
| C2 | 0.1074 (2) | −0.0775 (4) | 0.0594 (3) | 0.0510 (9) | |
| C3 | −0.0170 (2) | 0.1827 (4) | 0.0578 (4) | 0.0538 (9) | |
| C5 | 0.21822 (18) | 0.3830 (3) | 0.1102 (3) | 0.0351 (7) | |
| C6 | 0.29640 (19) | 0.4771 (4) | 0.2561 (3) | 0.0408 (8) | |
| C8 | 0.3950 (3) | 0.7473 (4) | 0.3512 (3) | 0.0612 (10) | |
| C9 | 0.4320 (4) | 0.9087 (6) | 0.2824 (5) | 0.0959 (16) | |
| H1A | 0.09019 | 0.16232 | −0.07339 | 0.0470* | |
| H2A | 0.17563 | −0.11100 | 0.03973 | 0.0765* | |
| H2C | 0.11134 | −0.11292 | 0.17142 | 0.0765* | |
| H3A | −0.01779 | 0.15625 | 0.16958 | 0.0807* | |
| H3B | −0.02803 | 0.31763 | 0.03897 | 0.0807* | |
| H4 | 0.19758 | 0.19341 | 0.25110 | 0.0488* | |
| H8A | 0.45613 | 0.67236 | 0.41350 | 0.0734* | |
| H8B | 0.35350 | 0.78659 | 0.42455 | 0.0734* | |
| H9A | 0.46887 | 0.99309 | 0.36911 | 0.1439* | |
| H9B | 0.48090 | 0.86902 | 0.22215 | 0.1439* | |
| H9C | 0.37114 | 0.97265 | 0.20956 | 0.1439* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O5 | 0.0666 (12) | 0.0448 (10) | 0.0277 (9) | −0.0073 (8) | 0.0075 (8) | 0.0008 (7) |
| O6 | 0.0943 (17) | 0.0790 (16) | 0.0334 (10) | −0.0371 (13) | −0.0064 (10) | 0.0085 (10) |
| O7 | 0.0598 (11) | 0.0439 (10) | 0.0374 (10) | −0.0125 (9) | 0.0038 (8) | −0.0031 (8) |
| N4 | 0.0455 (11) | 0.0487 (12) | 0.0235 (9) | −0.0084 (9) | 0.0032 (8) | −0.0001 (8) |
| C1 | 0.0447 (13) | 0.0436 (13) | 0.0262 (11) | −0.0064 (10) | 0.0053 (9) | 0.0005 (10) |
| C2 | 0.0395 (13) | 0.0488 (16) | 0.0578 (16) | 0.0028 (11) | 0.0028 (12) | −0.0106 (12) |
| C3 | 0.0476 (15) | 0.0409 (14) | 0.0657 (18) | 0.0054 (12) | 0.0050 (13) | −0.0172 (13) |
| C5 | 0.0370 (12) | 0.0391 (12) | 0.0288 (11) | 0.0012 (10) | 0.0090 (9) | −0.0034 (9) |
| C6 | 0.0414 (13) | 0.0473 (14) | 0.0323 (12) | −0.0041 (11) | 0.0083 (10) | −0.0011 (10) |
| C8 | 0.0722 (19) | 0.0604 (18) | 0.0436 (15) | −0.0205 (16) | 0.0049 (14) | −0.0138 (13) |
| C9 | 0.124 (3) | 0.086 (3) | 0.065 (2) | −0.053 (3) | 0.007 (2) | −0.0105 (19) |
Geometric parameters (Å, º) top
| O5—C5 | 1.221 (3) | C8—C9 | 1.453 (6) |
| O6—C6 | 1.193 (3) | C1—H1A | 1.0000 |
| O7—C6 | 1.306 (4) | C2—H2A | 0.9900 |
| O7—C8 | 1.465 (3) | C2—H2C | 0.9900 |
| N4—C1 | 1.457 (3) | C3—H3A | 0.9900 |
| N4—C5 | 1.321 (3) | C3—H3B | 0.9900 |
| N4—H4 | 0.8800 | C8—H8A | 0.9900 |
| C1—C2 | 1.510 (4) | C8—H8B | 0.9900 |
| C1—C3 | 1.511 (4) | C9—H9A | 0.9800 |
| C2—C3i | 1.525 (4) | C9—H9B | 0.9800 |
| C5—C6 | 1.538 (4) | C9—H9C | 0.9800 |
| | | |
| O5···O7 | 2.669 (3) | H1A···H3Ai | 2.5300 |
| O5···N4ii | 3.026 (3) | H1A···H4ii | 2.5700 |
| O6···C5iii | 3.398 (3) | H2A···O7x | 2.8100 |
| O6···N4 | 2.703 (3) | H2C···H3A | 2.5800 |
| O7···O5 | 2.669 (3) | H2C···H4 | 2.4900 |
| O5···H3Biv | 2.7900 | H2C···H1Ai | 2.5600 |
| O5···H4ii | 2.1900 | H2C···O5iii | 2.8100 |
| O5···H1A | 2.4800 | H3A···H2C | 2.5800 |
| O5···H2Cii | 2.8100 | H3A···H1Ai | 2.5300 |
| O5···H8Bv | 2.9100 | H3B···O5iv | 2.7900 |
| O6···H8A | 2.5500 | H4···O6 | 2.3200 |
| O6···H4 | 2.3200 | H4···H2C | 2.4900 |
| O6···H9Cvi | 2.8100 | H4···O5iii | 2.1900 |
| O6···H8B | 2.7500 | H4···C5iii | 3.0900 |
| O7···H2Avii | 2.8100 | H4···H1Aiii | 2.5700 |
| O7···H8Bv | 2.7100 | H8A···O6 | 2.5500 |
| N4···O6 | 2.703 (3) | H8B···O6 | 2.7500 |
| N4···O5iii | 3.026 (3) | H8B···O5vi | 2.9100 |
| C5···O6ii | 3.398 (3) | H8B···O7vi | 2.7100 |
| C5···H4ii | 3.0900 | H9A···C9ix | 3.0100 |
| C6···H9Bviii | 2.9800 | H9A···H9Aix | 2.1800 |
| C9···H9Aix | 3.0100 | H9B···C6xi | 2.9800 |
| H1A···O5 | 2.4800 | H9C···O6v | 2.8100 |
| H1A···H2Ci | 2.5600 | | |
| | | |
| C6—O7—C8 | 116.1 (2) | C1—C2—H2C | 110.00 |
| C1—N4—C5 | 123.37 (19) | H2A—C2—H2C | 108.00 |
| C5—N4—H4 | 118.00 | C3i—C2—H2A | 110.00 |
| C1—N4—H4 | 118.00 | C3i—C2—H2C | 110.00 |
| N4—C1—C3 | 110.5 (2) | C1—C3—H3A | 109.00 |
| N4—C1—C2 | 111.4 (2) | C1—C3—H3B | 109.00 |
| C2—C1—C3 | 110.7 (2) | H3A—C3—H3B | 108.00 |
| C1—C2—C3i | 110.4 (2) | C2i—C3—H3A | 109.00 |
| C1—C3—C2i | 111.7 (2) | C2i—C3—H3B | 109.00 |
| N4—C5—C6 | 112.4 (2) | O7—C8—H8A | 110.00 |
| O5—C5—N4 | 126.0 (2) | O7—C8—H8B | 110.00 |
| O5—C5—C6 | 121.6 (2) | C9—C8—H8A | 110.00 |
| O6—C6—O7 | 125.4 (3) | C9—C8—H8B | 110.00 |
| O6—C6—C5 | 122.9 (3) | H8A—C8—H8B | 108.00 |
| O7—C6—C5 | 111.7 (2) | C8—C9—H9A | 109.00 |
| O7—C8—C9 | 107.7 (2) | C8—C9—H9B | 109.00 |
| N4—C1—H1A | 108.00 | C8—C9—H9C | 109.00 |
| C2—C1—H1A | 108.00 | H9A—C9—H9B | 110.00 |
| C3—C1—H1A | 108.00 | H9A—C9—H9C | 109.00 |
| C1—C2—H2A | 110.00 | H9B—C9—H9C | 109.00 |
| | | |
| C6—O7—C8—C9 | 173.3 (3) | N4—C1—C2—C3i | 179.2 (2) |
| C8—O7—C6—C5 | 174.4 (2) | C3—C1—C2—C3i | 55.8 (3) |
| C8—O7—C6—O6 | −4.1 (4) | N4—C1—C3—C2i | 179.5 (2) |
| C5—N4—C1—C2 | 137.8 (2) | C1—C2—C3i—C1i | −56.3 (3) |
| C5—N4—C1—C3 | −98.6 (3) | O5—C5—C6—O7 | 6.5 (4) |
| C1—N4—C5—C6 | 173.5 (2) | N4—C5—C6—O6 | 7.1 (4) |
| C1—N4—C5—O5 | −4.4 (4) | N4—C5—C6—O7 | −171.5 (2) |
| C2—C1—C3—C2i | −56.6 (3) | O5—C5—C6—O6 | −174.9 (3) |
| Symmetry codes: (i) −x, −y, −z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, −y+1, −z; (v) x, −y+3/2, z−1/2; (vi) x, −y+3/2, z+1/2; (vii) x, y+1, z; (viii) −x+1, y−1/2, −z+1/2; (ix) −x+1, −y+2, −z+1; (x) x, y−1, z; (xi) −x+1, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4···O6 | 0.88 | 2.32 | 2.703 (3) | 106 |
| N4—H4···O5iii | 0.88 | 2.19 | 3.026 (3) | 160 |
| C1—H1A···O5 | 1.00 | 2.48 | 2.849 (3) | 102 |
| Symmetry code: (iii) x, −y+1/2, z+1/2. |
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![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.004 Å
Alert level C
