Diethyl N,N′-o-phenyl­enedioxamate

Martín, S.; Beitia, J.I.; Ugalde, M.; Vitoria, P.; Cortés, R.

doi:10.1107/S1600536802012849

Diethyl N,N′-o-phenylenedioxamate

S. Martín, J. I. Beitia, M. Ugalde, P. Vitoria and R. Cortés

The crystal structure analysis of the title compound, C₆H₄(NHC₂O₃C₂H₅)₂ or C₁₄H₁₆N₂O₆, reveals a molecule with both oxamate groups twisted with respect to the benzene ring, as a result of steric interactions and the presence of three strong N—H

O and one weak C—H

O intramolecular hydrogen bonds. Centrosymmetrically related molecules form dimers connected by two N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012849/cv6126sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012849/cv6126Isup2.hkl Contains datablock I

CCDC reference: 193771

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.058
wR factor = 0.155
Data-to-parameter ratio = 19.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C(15)  -   C(16)  =       1.53 Ang.

PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C(25)  -   C(26)  =       1.53 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Diethyl N,N'-o-phenylenedioxamate top

Crystal data top

C₁₄H₁₆N₂O₆	F(000) = 1296
M_r = 308.29	D_x = 1.35 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 17.756 (4) Å	θ = 8.1–13.3°
b = 15.986 (2) Å	µ = 0.11 mm⁻¹
c = 11.924 (2) Å	T = 293 K
β = 116.31 (2)°	Prism, colourless
V = 3034.0 (9) Å³	0.5 × 0.45 × 0.4 mm
Z = 8

Data collection top

Enraf-Nonius CAD-4 diffractometer	θ_max = 30.0°, θ_min = 1.8°
Radiation source: x-ray tube	h = −24→22
ω/2θ scans	k = 0→22
4616 measured reflections	l = 0→16
4419 independent reflections	2 standard reflections every 100 reflections
1870 reflections with I > 2σ(I)	intensity decay: <2%
R_int = 0.033

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.058	w = 1/[σ²(F_o²) + (0.0787P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.155	(Δ/σ)_max = 0.001
S = 0.88	Δρ_max = 0.30 e Å⁻³
4419 reflections	Δρ_min = −0.32 e Å⁻³
225 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 on F^{2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted} ^R^-factors ^wR ^{and all goodnesses of fit} ^S ^{are based on} ^F2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of} ^F2 > σ(F^{2) is used only for calculating -}^R^-factor-obs ^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	U_iso*/U_eq
O11	0.30947 (9)	0.44780 (9)	0.20955 (15)	0.0496 (5)
O12	0.45722 (11)	0.41860 (10)	0.09620 (18)	0.0660 (7)
O13	0.39557 (10)	0.53614 (9)	0.11387 (16)	0.0568 (6)
O21	0.04859 (10)	0.29476 (10)	−0.06548 (16)	0.0606 (6)
O22	−0.00916 (11)	0.45875 (11)	−0.12672 (18)	0.0732 (7)
O23	0.12641 (9)	0.49507 (9)	−0.03691 (16)	0.0604 (5)
N14	0.34765 (11)	0.32775 (11)	0.14555 (16)	0.0394 (6)
N24	0.17204 (10)	0.35130 (11)	0.07758 (16)	0.0405 (6)
C11	0.29423 (17)	0.12977 (15)	0.2499 (2)	0.0554 (9)
C12	0.33941 (15)	0.19324 (13)	0.2298 (2)	0.0481 (7)
C13	0.29909 (12)	0.26735 (11)	0.17272 (18)	0.0351 (6)
C15	0.34985 (12)	0.41029 (12)	0.16542 (19)	0.0383 (7)
C16	0.40785 (13)	0.45493 (14)	0.1210 (2)	0.0453 (7)
C17	0.44273 (19)	0.58358 (15)	0.0617 (3)	0.0725 (11)
C18	0.4155 (2)	0.67201 (18)	0.0473 (4)	0.0983 (14)
C21	0.21045 (17)	0.13929 (15)	0.2165 (2)	0.0587 (9)
C22	0.17024 (15)	0.21320 (14)	0.1629 (2)	0.0495 (8)
C23	0.21386 (12)	0.27717 (11)	0.13782 (18)	0.0374 (6)
C25	0.09354 (13)	0.35450 (13)	−0.0171 (2)	0.0429 (7)
C26	0.06317 (14)	0.44294 (13)	−0.0666 (2)	0.0469 (7)
C27	0.10721 (18)	0.58054 (15)	−0.0863 (3)	0.0782 (10)
C28	0.1802 (3)	0.6121 (2)	−0.0957 (4)	0.130 (2)
H11	0.3187 (14)	0.0795 (13)	0.286 (2)	0.049 (6)*
H12	0.4033 (16)	0.1896 (15)	0.258 (2)	0.068 (7)*
H14	0.3820 (14)	0.3114 (14)	0.123 (2)	0.047 (7)*
H21	0.1807 (16)	0.0988 (16)	0.236 (2)	0.071 (8)*
H22	0.1077 (15)	0.2216 (13)	0.135 (2)	0.060 (7)*
H24	0.2030 (13)	0.3986 (14)	0.098 (2)	0.047 (6)*
H171	0.50240	0.57990	0.11690	0.0870*
H172	0.43280	0.56060	−0.01890	0.0870*
H181	0.42470	0.69410	0.12720	0.1480*
H182	0.44730	0.70390	0.01490	0.1480*
H183	0.35680	0.67540	−0.00950	0.1480*
H271	0.05910	0.58040	−0.16800	0.0940*
H272	0.09430	0.61550	−0.03070	0.0940*
H281	0.19220	0.57720	−0.15130	0.1940*
H282	0.16970	0.66820	−0.12770	0.1940*
H283	0.22740	0.61190	−0.01450	0.1940*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0526 (9)	0.0412 (8)	0.0690 (10)	−0.0089 (7)	0.0397 (8)	−0.0162 (8)
O12	0.0689 (12)	0.0535 (10)	0.1036 (15)	−0.0018 (8)	0.0637 (12)	−0.0019 (9)
O13	0.0651 (10)	0.0382 (9)	0.0866 (12)	−0.0061 (7)	0.0513 (10)	−0.0004 (8)
O21	0.0443 (9)	0.0489 (9)	0.0727 (11)	−0.0095 (7)	0.0116 (8)	−0.0006 (8)
O22	0.0464 (10)	0.0658 (11)	0.0866 (13)	0.0090 (9)	0.0105 (9)	0.0107 (11)
O23	0.0513 (9)	0.0396 (8)	0.0747 (11)	0.0004 (7)	0.0137 (8)	0.0159 (8)
N14	0.0388 (10)	0.0345 (10)	0.0495 (11)	−0.0002 (7)	0.0237 (8)	−0.0029 (8)
N24	0.0349 (9)	0.0330 (9)	0.0499 (11)	−0.0008 (8)	0.0155 (8)	0.0035 (8)
C11	0.0683 (17)	0.0373 (13)	0.0560 (15)	0.0071 (12)	0.0233 (12)	0.0140 (11)
C12	0.0497 (13)	0.0417 (12)	0.0482 (13)	0.0056 (10)	0.0173 (11)	0.0018 (10)
C13	0.0377 (11)	0.0303 (10)	0.0371 (11)	−0.0017 (8)	0.0165 (9)	−0.0015 (8)
C15	0.0375 (11)	0.0349 (11)	0.0401 (12)	−0.0043 (8)	0.0149 (10)	−0.0046 (9)
C16	0.0427 (12)	0.0440 (13)	0.0529 (13)	−0.0055 (10)	0.0245 (11)	−0.0047 (11)
C17	0.0810 (19)	0.0561 (16)	0.103 (2)	−0.0129 (14)	0.0613 (18)	0.0102 (15)
C18	0.099 (2)	0.0618 (19)	0.154 (3)	−0.0031 (17)	0.074 (2)	0.032 (2)
C21	0.0675 (17)	0.0451 (13)	0.0649 (16)	−0.0080 (12)	0.0305 (13)	0.0156 (12)
C22	0.0466 (13)	0.0481 (13)	0.0572 (14)	−0.0053 (11)	0.0260 (11)	0.0070 (11)
C23	0.0394 (11)	0.0317 (10)	0.0401 (11)	−0.0021 (8)	0.0168 (9)	0.0014 (8)
C25	0.0382 (11)	0.0422 (12)	0.0491 (13)	−0.0007 (10)	0.0202 (10)	0.0024 (10)
C26	0.0423 (12)	0.0440 (12)	0.0507 (13)	0.0025 (10)	0.0173 (11)	0.0018 (10)
C27	0.0776 (19)	0.0430 (14)	0.087 (2)	0.0012 (13)	0.0119 (16)	0.0205 (14)
C28	0.168 (4)	0.072 (2)	0.193 (5)	0.010 (3)	0.120 (4)	0.046 (3)

Geometric parameters (Å, º) top

O11—C15	1.219 (3)	C17—C18	1.479 (4)
O12—C16	1.193 (3)	C21—C22	1.382 (3)
O13—C16	1.313 (3)	C22—C23	1.393 (3)
O13—C17	1.458 (4)	C25—C26	1.535 (3)
O21—C25	1.214 (3)	C27—C28	1.441 (6)
O22—C26	1.188 (3)	C11—H11	0.92 (2)
O23—C26	1.315 (3)	C12—H12	1.03 (3)
O23—C27	1.467 (3)	C17—H171	0.97
N14—C13	1.424 (3)	C17—H172	0.97
N14—C15	1.338 (3)	C18—H181	0.96
N24—C23	1.414 (3)	C18—H182	0.96
N24—C25	1.351 (3)	C18—H183	0.96
N14—H14	0.81 (3)	C21—H21	0.93 (3)
N24—H24	0.90 (2)	C22—H22	1.02 (3)
C11—C12	1.379 (4)	C27—H271	0.97
C11—C21	1.367 (4)	C27—H272	0.97
C12—C13	1.395 (3)	C28—H281	0.96
C13—C23	1.389 (3)	C28—H282	0.96
C15—C16	1.528 (3)	C28—H283	0.96

O11···O13	2.679 (3)	C15···O12ⁱⁱ	3.347 (3)
O11···N24	2.722 (3)	C16···C16ⁱⁱ	3.354 (3)
O11···C23	3.125 (3)	C16···O12ⁱⁱ	3.207 (3)
O11···C21ⁱ	3.248 (3)	C17···O12ⁱⁱⁱ	3.109 (4)
O12···C15ⁱⁱ	3.347 (3)	C21···O11^ix	3.248 (3)
O12···C17ⁱⁱⁱ	3.109 (4)	C22···O21	2.927 (3)
O12···N14	2.694 (3)	C23···O11	3.125 (3)
O12···C16ⁱⁱ	3.207 (3)	C25···C12^iv	3.333 (4)
O13···O11	2.679 (3)	C26···O22^vi	3.265 (3)
O21···O22	2.792 (3)	C26···O22^v	3.354 (3)
O21···C22	2.927 (3)	C11···H272^ix	3.0505
O21···C12^iv	3.359 (3)	C15···H24	2.37 (3)
O21···N14^iv	3.115 (3)	C25···H22	2.73 (2)
O22···C26^v	3.354 (3)	C25···H14^iv	3.05 (2)
O22···C26^vi	3.265 (3)	C25···H12^iv	2.98 (2)
O22···O22^vi	3.179 (3)	C28···H183	3.0093
O22···O22^v	3.098 (3)	H11···O22^x	2.82 (3)
O22···O21	2.792 (3)	H12···H14	2.45 (3)
O23···N24	2.612 (2)	H12···O21^iv	2.79 (3)
O11···H24	1.93 (2)	H12···C25^iv	2.98 (2)
O11···H21ⁱ	2.49 (3)	H12···O21^x	2.52 (3)
O12···H172	2.5879	H12···O22^x	2.83 (2)
O12···H171	2.6791	H14···O12	2.28 (2)
O12···H14	2.28 (2)	H14···H12	2.45 (3)
O12···H172ⁱⁱⁱ	2.5237	H14···O21^iv	2.37 (2)
O13···H21ⁱ	2.86 (3)	H14···C25^iv	3.05 (2)
O21···H22	2.44 (2)	H21···O11^ix	2.49 (3)
O21···H12^vii	2.52 (3)	H21···O13^ix	2.86 (3)
O21···H182^viii	2.7912	H22···O21	2.44 (2)
O21···H12^iv	2.79 (3)	H22···C25	2.73 (2)
O21···H14^iv	2.37 (2)	H22···H182^viii	2.5743
O22···H11^vii	2.82 (3)	H24···O11	1.93 (2)
O22···H12^vii	2.83 (2)	H24···O23	2.21 (2)
O22···H271	2.4540	H24···N14	2.63 (2)
O23···H24	2.21 (2)	H24···C15	2.37 (3)
N14···O12	2.694 (3)	H171···O12	2.6791
N14···N24	2.878 (3)	H172···O12	2.5879
N14···O21^iv	3.115 (3)	H172···O12ⁱⁱⁱ	2.5237
N24···O23	2.612 (2)	H182···O21^xi	2.7912
N24···O11	2.722 (3)	H182···H22^xi	2.5743
N24···N14	2.878 (3)	H183···C28	3.0093
N24···C15	3.004 (3)	H183···H283	2.4883
N14···H24	2.63 (2)	H271···O22	2.4540
C12···O21^iv	3.359 (3)	H271···H271^v	2.1426
C12···C25^iv	3.333 (4)	H272···C11ⁱ	3.0505
C15···N24	3.004 (3)	H283···H183	2.4883

C16—O13—C17	115.6 (2)	O23—C27—C28	107.5 (3)
C26—O23—C27	117.6 (2)	C12—C11—H11	122.1 (17)
C13—N14—C15	127.0 (2)	C21—C11—H11	117.3 (17)
C23—N24—C25	124.84 (18)	C11—C12—H12	122.8 (13)
C15—N14—H14	114.2 (16)	C13—C12—H12	117.3 (13)
C13—N14—H14	118.5 (16)	O13—C17—H171	109.9
C23—N24—H24	116.4 (15)	O13—C17—H172	109.9
C25—N24—H24	118.2 (14)	C18—C17—H171	109.9
C12—C11—C21	120.6 (2)	C18—C17—H172	109.9
C11—C12—C13	119.8 (3)	H171—C17—H172	108.5
N14—C13—C12	117.1 (2)	C17—C18—H181	109.5
N14—C13—C23	122.97 (17)	C17—C18—H182	109.5
C12—C13—C23	119.8 (2)	C17—C18—H183	109.5
O11—C15—C16	122.41 (18)	H181—C18—H182	109.5
N14—C15—C16	111.75 (19)	H181—C18—H183	109.5
O11—C15—N14	125.8 (2)	H182—C18—H183	109.5
O12—C16—O13	125.8 (2)	C11—C21—H21	121.1 (17)
O12—C16—C15	122.7 (2)	C22—C21—H21	118.5 (17)
O13—C16—C15	111.5 (2)	C21—C22—H22	122.0 (12)
O13—C17—C18	109.1 (3)	C23—C22—H22	117.6 (12)
C11—C21—C22	120.1 (3)	O23—C27—H271	110.2
C21—C22—C23	120.3 (3)	O23—C27—H272	110.2
N24—C23—C22	120.5 (2)	C28—C27—H271	110.2
C13—C23—C22	119.23 (19)	C28—C27—H272	110.2
N24—C23—C13	120.27 (18)	H271—C27—H272	108.5
O21—C25—N24	125.8 (2)	C27—C28—H281	109.5
O21—C25—C26	119.8 (2)	C27—C28—H282	109.5
N24—C25—C26	114.38 (19)	C27—C28—H283	109.5
O22—C26—C25	122.0 (2)	H281—C28—H282	109.5
O23—C26—C25	111.6 (2)	H281—C28—H283	109.5
O22—C26—O23	126.4 (2)	H282—C28—H283	109.5

C17—O13—C16—O12	5.0 (3)	C11—C12—C13—N14	−175.12 (19)
C17—O13—C16—C15	−174.8 (2)	C12—C13—C23—N24	−178.68 (18)
C16—O13—C17—C18	174.0 (3)	C12—C13—C23—C22	1.3 (3)
C27—O23—C26—O22	−2.7 (4)	N14—C13—C23—C22	176.97 (19)
C27—O23—C26—C25	175.4 (2)	N14—C13—C23—N24	−3.0 (3)
C26—O23—C27—C28	−152.9 (3)	N14—C15—C16—O13	165.54 (18)
C15—N14—C13—C12	−135.6 (2)	N14—C15—C16—O12	−14.2 (3)
C13—N14—C15—C16	−178.54 (19)	O11—C15—C16—O13	−12.3 (3)
C13—N14—C15—O11	−0.7 (4)	O11—C15—C16—O12	167.9 (2)
C15—N14—C13—C23	48.6 (3)	C11—C21—C22—C23	2.6 (3)
C23—N24—C25—O21	−1.6 (4)	C21—C22—C23—C13	−3.0 (3)
C23—N24—C25—C26	−179.5 (2)	C21—C22—C23—N24	176.98 (19)
C25—N24—C23—C13	140.9 (2)	O21—C25—C26—O23	−157.8 (2)
C25—N24—C23—C22	−39.1 (3)	N24—C25—C26—O22	−161.5 (2)
C12—C11—C21—C22	−0.5 (3)	O21—C25—C26—O22	20.4 (4)
C21—C11—C12—C13	−1.2 (3)	N24—C25—C26—O23	20.3 (3)
C11—C12—C13—C23	0.8 (3)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, y, −z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+1/2, −y+1/2, −z; (v) −x, y, −z−1/2; (vi) −x, −y+1, −z; (vii) x−1/2, −y+1/2, z−1/2; (viii) x−1/2, y−1/2, z; (ix) −x+1/2, y−1/2, −z+1/2; (x) x+1/2, −y+1/2, z+1/2; (xi) x+1/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O12	0.81 (3)	2.28 (2)	2.694 (3)	112.2 (19)
N24—H24···O11	0.90 (2)	1.93 (2)	2.722 (3)	145 (2)
N24—H24···O23	0.90 (2)	2.21 (2)	2.612 (2)	106.5 (17)
C22—H22···O21	1.02 (3)	2.44 (2)	2.927 (3)	108.5 (16)
N14—H14···O21^iv	0.81 (3)	2.37 (2)	3.115 (3)	153 (2)
C17—H172···O12ⁱⁱⁱ	0.97	2.52	3.109 (4)	119
C21—H21···O11^ix	0.93 (3)	2.49 (3)	3.248 (3)	140 (2)
C12—H12···O21^x	1.03 (3)	2.52 (3)	3.428 (3)	146.9 (18)

Symmetry codes: (iii) −x+1, −y+1, −z; (iv) −x+1/2, −y+1/2, −z; (ix) −x+1/2, y−1/2, −z+1/2; (x) x+1/2, −y+1/2, z+1/2.

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Diethyl N,N′-o-phenyl­enedioxamate

Supporting information

Key indicators

checkCIF results

Diethyl N,N′-o-phenylenedioxamate