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organic compounds
Diethyl N,N′-(p-phenylene)dioxamate
aSchool of Life Sciences, Northeast Normal University, Changchun 130024, People's Republic of China, and bCollege of Sciences, Shenyang Agricultural University, Shenyang 110161, People's Republic of China
*Correspondence e-mail: liuxiaoyu126@yahoo.cn
In the 14H16N2O6, is located on an inversion centre. The amide –NHCO– plane makes a dihedral angle of 34.08 (9)° with the benzene ring. The molecules are connected via intermolecular O—H⋯N hydrogen bonds into a two-dimensional network parallel to the bc plane. An intramolecular N—H⋯O hydrogen bond is also observed.
the molecule of the title compound, CRelated literature
For related literature, see: Hashmi et al. (2004); Navarro et al. (1998
); Nonoyama et al. (1982
); Pardo et al. (2003
); Rios-Moreno et al. (2003
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL-Plus (Sheldrick, 2008
); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808027190/is2327sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808027190/is2327Isup2.hkl
The synthesis method of the title compound is according to the previous literature method (Pardo et al., 2003). Colorless single crystals suitable for experiments were obtained from a methanol solution. Elemental analysis calculated for C14H16N2O6: C 54.54, H 5.23, N 9.09%; found C 54.52, H 5.22, N 9.08%. IR data: 3249 cm-1 (m, N—H), 1682 cm-1 (s, C=O).
The H atom attached to the N atom was located in a different Fourier map and refined freely. Other hydrogen atoms were positioned geometrically with bond lengths C—H = 0.93–0.97 Å, and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(aromatic C) or 1.5Ueq(methyl C).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C14H16N2O6 | F(000) = 324 |
Mr = 308.29 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 2859 reflections |
a = 11.328 (5) Å | θ = 2.2–27.0° |
b = 7.769 (5) Å | µ = 0.11 mm−1 |
c = 8.372 (5) Å | T = 295 K |
β = 95.566 (5)° | Sheet, colorless |
V = 733.3 (7) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 2 |
Bruker APEXII CCD area-detector diffractometer | 1285 independent reflections |
Radiation source: fine-focus sealed tube | 1075 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −12→13 |
Tmin = 0.975, Tmax = 0.989 | k = −9→8 |
5037 measured reflections | l = −9→9 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0715P)2 + 0.3357P] where P = (Fo2 + 2Fc2)/3 |
1285 reflections | (Δ/σ)max = 0.022 |
104 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C14H16N2O6 | V = 733.3 (7) Å3 |
Mr = 308.29 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.328 (5) Å | µ = 0.11 mm−1 |
b = 7.769 (5) Å | T = 295 K |
c = 8.372 (5) Å | 0.3 × 0.2 × 0.1 mm |
β = 95.566 (5)° |
Bruker APEXII CCD area-detector diffractometer | 1285 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1075 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.989 | Rint = 0.017 |
5037 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.33 e Å−3 |
1285 reflections | Δρmin = −0.19 e Å−3 |
104 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.70158 (18) | 0.6118 (2) | 0.73921 (19) | 0.0770 (6) | |
O2 | 0.68604 (16) | 0.3705 (2) | 0.59603 (19) | 0.0759 (6) | |
O3 | 0.82720 (14) | 0.44460 (17) | 0.97740 (16) | 0.0564 (5) | |
N1 | 0.84872 (15) | 0.2185 (2) | 0.8077 (2) | 0.0475 (5) | |
H1N | 0.826 (2) | 0.183 (3) | 0.714 (3) | 0.058 (6)* | |
C1 | 0.92637 (16) | 0.1107 (2) | 0.9062 (2) | 0.0433 (5) | |
C2 | 0.91424 (18) | −0.0652 (3) | 0.8901 (2) | 0.0530 (5) | |
H2 | 0.8563 | −0.1096 | 0.8150 | 0.064* | |
C3 | 1.01346 (18) | 0.1763 (3) | 1.0168 (2) | 0.0515 (5) | |
H3 | 1.0232 | 0.2947 | 1.0282 | 0.062* | |
C4 | 0.80684 (17) | 0.3714 (2) | 0.8486 (2) | 0.0443 (5) | |
C5 | 0.72433 (18) | 0.4498 (3) | 0.7117 (2) | 0.0503 (5) | |
C6 | 0.6271 (4) | 0.7022 (4) | 0.6127 (4) | 0.1143 (14) | |
H6A | 0.6762 | 0.7417 | 0.5314 | 0.137* | |
H6B | 0.5689 | 0.6227 | 0.5622 | 0.137* | |
C7 | 0.5702 (4) | 0.8389 (6) | 0.6711 (5) | 0.1472 (19) | |
H7A | 0.5245 | 0.8966 | 0.5846 | 0.221* | |
H7B | 0.6275 | 0.9172 | 0.7224 | 0.221* | |
H7C | 0.5185 | 0.7995 | 0.7478 | 0.221* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1129 (14) | 0.0571 (10) | 0.0539 (9) | 0.0175 (9) | −0.0278 (9) | 0.0023 (8) |
O2 | 0.0842 (12) | 0.0826 (12) | 0.0549 (10) | 0.0192 (9) | −0.0235 (9) | −0.0186 (9) |
O3 | 0.0795 (10) | 0.0479 (8) | 0.0392 (8) | 0.0048 (7) | −0.0080 (7) | −0.0032 (6) |
N1 | 0.0564 (10) | 0.0515 (10) | 0.0332 (9) | 0.0021 (7) | −0.0034 (7) | −0.0044 (7) |
C1 | 0.0476 (10) | 0.0482 (11) | 0.0338 (9) | 0.0006 (8) | 0.0026 (8) | −0.0021 (8) |
C2 | 0.0536 (11) | 0.0516 (12) | 0.0507 (12) | −0.0030 (9) | −0.0110 (9) | −0.0099 (9) |
C3 | 0.0556 (11) | 0.0422 (11) | 0.0545 (12) | −0.0030 (9) | −0.0054 (9) | −0.0054 (9) |
C4 | 0.0523 (10) | 0.0454 (10) | 0.0346 (10) | −0.0041 (8) | 0.0012 (8) | 0.0024 (8) |
C5 | 0.0558 (11) | 0.0541 (12) | 0.0400 (11) | 0.0022 (9) | 0.0000 (9) | −0.0005 (9) |
C6 | 0.176 (4) | 0.089 (2) | 0.0665 (17) | 0.046 (2) | −0.047 (2) | 0.0065 (16) |
C7 | 0.162 (4) | 0.172 (4) | 0.102 (3) | 0.092 (3) | −0.017 (3) | 0.032 (3) |
O1—C5 | 1.310 (3) | C2—H2 | 0.9300 |
O1—C6 | 1.467 (3) | C3—C2i | 1.379 (3) |
O2—C5 | 1.193 (2) | C3—H3 | 0.9300 |
O3—C4 | 1.221 (2) | C4—C5 | 1.533 (3) |
N1—C4 | 1.336 (3) | C6—C7 | 1.358 (5) |
N1—C1 | 1.419 (2) | C6—H6A | 0.9700 |
N1—H1N | 0.85 (2) | C6—H6B | 0.9700 |
C1—C2 | 1.379 (3) | C7—H7A | 0.9600 |
C1—C3 | 1.383 (3) | C7—H7B | 0.9600 |
C2—C3i | 1.379 (3) | C7—H7C | 0.9600 |
C4—N1—C1 | 126.25 (17) | C7—C6—O1 | 111.9 (3) |
C4—N1—H1N | 116.1 (15) | C7—C6—H6A | 109.2 |
C1—N1—H1N | 117.6 (15) | O1—C6—H6A | 109.2 |
C5—O1—C6 | 116.2 (2) | C7—C6—H6B | 109.2 |
O3—C4—N1 | 126.80 (18) | O1—C6—H6B | 109.2 |
O3—C4—C5 | 121.63 (18) | H6A—C6—H6B | 107.9 |
N1—C4—C5 | 111.56 (16) | C1—C2—C3i | 121.15 (19) |
C2—C1—C3 | 119.26 (18) | C1—C2—H2 | 119.4 |
C2—C1—N1 | 118.55 (17) | C3i—C2—H2 | 119.4 |
C3—C1—N1 | 122.19 (18) | C6—C7—H7A | 109.5 |
O2—C5—O1 | 125.2 (2) | C6—C7—H7B | 109.5 |
O2—C5—C4 | 123.3 (2) | H7A—C7—H7B | 109.5 |
O1—C5—C4 | 111.49 (17) | C6—C7—H7C | 109.5 |
C2i—C3—C1 | 119.58 (19) | H7A—C7—H7C | 109.5 |
C2i—C3—H3 | 120.2 | H7B—C7—H7C | 109.5 |
C1—C3—H3 | 120.2 |
Symmetry code: (i) −x+2, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.85 (2) | 2.30 (2) | 2.701 (3) | 109.0 (19) |
N1—H1N···O3ii | 0.85 (2) | 2.21 (3) | 3.030 (3) | 161 (2) |
Symmetry code: (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H16N2O6 |
Mr | 308.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 11.328 (5), 7.769 (5), 8.372 (5) |
β (°) | 95.566 (5) |
V (Å3) | 733.3 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.975, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5037, 1285, 1075 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.136, 1.00 |
No. of reflections | 1285 |
No. of parameters | 104 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.19 |
Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.85 (2) | 2.30 (2) | 2.701 (3) | 109.0 (19) |
N1—H1N···O3i | 0.85 (2) | 2.21 (3) | 3.030 (3) | 161 (2) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Acknowledgements
We thank the Analysis and Testing Foundation of Northeast Normal University for financial support.
References
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Oxamido ligands were extensively investigated owing to their special biological properties and application prospects (Nonoyama et al., 1982). However, the ligands of oxalamic acid ethyl ester were rarely reported, in which ester group can stabilize the final compounds by producing complexes with main group and transition metals (Rios-Moreno et al., 2003). In this work, the title compound, (I), was characterized by XRD single-crystal diffraction, element analysis and IR.
In the molecule (Fig. 1), the bond lengths containing O and N atoms are all consistent with corresponding values observed in similar systems (Navarro et al., 1998; Hashmi et al., 2004). There exists an intermolecular hydrogen bond involving the carboxamide O atom and the carboxamide N atom with a distance of 3.030 (3) Å, which are in agreement with those found in related compounds. Simultaneously, the molecule units are assembled into two dimensional structure with the intermolecular hydrogen-bond interactions.