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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012849/cv6126sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012849/cv6126Isup2.hkl
Contains datablock I

CCDC reference: 193771

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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


Yellow Alert 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
C14H16N2O6F(000) = 1296
Mr = 308.29Dx = 1.35 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 17.756 (4) Åθ = 8.1–13.3°
b = 15.986 (2) ŵ = 0.11 mm1
c = 11.924 (2) ÅT = 293 K
β = 116.31 (2)°Prism, colourless
V = 3034.0 (9) Å30.5 × 0.45 × 0.4 mm
Z = 8
Data collection top
Enraf-Nonius CAD-4
diffractometer
θmax = 30.0°, θmin = 1.8°
Radiation source: x-ray tubeh = 2422
ω/2θ scansk = 022
4616 measured reflectionsl = 016
4419 independent reflections2 standard reflections every 100 reflections
1870 reflections with I > 2σ(I) intensity decay: <2%
Rint = 0.033
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.0787P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.155(Δ/σ)max = 0.001
S = 0.88Δρmax = 0.30 e Å3
4419 reflectionsΔρmin = 0.32 e Å3
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 F2 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 F2. The observed criterion of F2 > σ(F2) 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
xyzUiso*/Ueq
O110.30947 (9)0.44780 (9)0.20955 (15)0.0496 (5)
O120.45722 (11)0.41860 (10)0.09620 (18)0.0660 (7)
O130.39557 (10)0.53614 (9)0.11387 (16)0.0568 (6)
O210.04859 (10)0.29476 (10)0.06548 (16)0.0606 (6)
O220.00916 (11)0.45875 (11)0.12672 (18)0.0732 (7)
O230.12641 (9)0.49507 (9)0.03691 (16)0.0604 (5)
N140.34765 (11)0.32775 (11)0.14555 (16)0.0394 (6)
N240.17204 (10)0.35130 (11)0.07758 (16)0.0405 (6)
C110.29423 (17)0.12977 (15)0.2499 (2)0.0554 (9)
C120.33941 (15)0.19324 (13)0.2298 (2)0.0481 (7)
C130.29909 (12)0.26735 (11)0.17272 (18)0.0351 (6)
C150.34985 (12)0.41029 (12)0.16542 (19)0.0383 (7)
C160.40785 (13)0.45493 (14)0.1210 (2)0.0453 (7)
C170.44273 (19)0.58358 (15)0.0617 (3)0.0725 (11)
C180.4155 (2)0.67201 (18)0.0473 (4)0.0983 (14)
C210.21045 (17)0.13929 (15)0.2165 (2)0.0587 (9)
C220.17024 (15)0.21320 (14)0.1629 (2)0.0495 (8)
C230.21386 (12)0.27717 (11)0.13782 (18)0.0374 (6)
C250.09354 (13)0.35450 (13)0.0171 (2)0.0429 (7)
C260.06317 (14)0.44294 (13)0.0666 (2)0.0469 (7)
C270.10721 (18)0.58054 (15)0.0863 (3)0.0782 (10)
C280.1802 (3)0.6121 (2)0.0957 (4)0.130 (2)
H110.3187 (14)0.0795 (13)0.286 (2)0.049 (6)*
H120.4033 (16)0.1896 (15)0.258 (2)0.068 (7)*
H140.3820 (14)0.3114 (14)0.123 (2)0.047 (7)*
H210.1807 (16)0.0988 (16)0.236 (2)0.071 (8)*
H220.1077 (15)0.2216 (13)0.135 (2)0.060 (7)*
H240.2030 (13)0.3986 (14)0.098 (2)0.047 (6)*
H1710.502400.579900.116900.0870*
H1720.432800.560600.018900.0870*
H1810.424700.694100.127200.1480*
H1820.447300.703900.014900.1480*
H1830.356800.675400.009500.1480*
H2710.059100.580400.168000.0940*
H2720.094300.615500.030700.0940*
H2810.192200.577200.151300.1940*
H2820.169700.668200.127700.1940*
H2830.227400.611900.014500.1940*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0526 (9)0.0412 (8)0.0690 (10)0.0089 (7)0.0397 (8)0.0162 (8)
O120.0689 (12)0.0535 (10)0.1036 (15)0.0018 (8)0.0637 (12)0.0019 (9)
O130.0651 (10)0.0382 (9)0.0866 (12)0.0061 (7)0.0513 (10)0.0004 (8)
O210.0443 (9)0.0489 (9)0.0727 (11)0.0095 (7)0.0116 (8)0.0006 (8)
O220.0464 (10)0.0658 (11)0.0866 (13)0.0090 (9)0.0105 (9)0.0107 (11)
O230.0513 (9)0.0396 (8)0.0747 (11)0.0004 (7)0.0137 (8)0.0159 (8)
N140.0388 (10)0.0345 (10)0.0495 (11)0.0002 (7)0.0237 (8)0.0029 (8)
N240.0349 (9)0.0330 (9)0.0499 (11)0.0008 (8)0.0155 (8)0.0035 (8)
C110.0683 (17)0.0373 (13)0.0560 (15)0.0071 (12)0.0233 (12)0.0140 (11)
C120.0497 (13)0.0417 (12)0.0482 (13)0.0056 (10)0.0173 (11)0.0018 (10)
C130.0377 (11)0.0303 (10)0.0371 (11)0.0017 (8)0.0165 (9)0.0015 (8)
C150.0375 (11)0.0349 (11)0.0401 (12)0.0043 (8)0.0149 (10)0.0046 (9)
C160.0427 (12)0.0440 (13)0.0529 (13)0.0055 (10)0.0245 (11)0.0047 (11)
C170.0810 (19)0.0561 (16)0.103 (2)0.0129 (14)0.0613 (18)0.0102 (15)
C180.099 (2)0.0618 (19)0.154 (3)0.0031 (17)0.074 (2)0.032 (2)
C210.0675 (17)0.0451 (13)0.0649 (16)0.0080 (12)0.0305 (13)0.0156 (12)
C220.0466 (13)0.0481 (13)0.0572 (14)0.0053 (11)0.0260 (11)0.0070 (11)
C230.0394 (11)0.0317 (10)0.0401 (11)0.0021 (8)0.0168 (9)0.0014 (8)
C250.0382 (11)0.0422 (12)0.0491 (13)0.0007 (10)0.0202 (10)0.0024 (10)
C260.0423 (12)0.0440 (12)0.0507 (13)0.0025 (10)0.0173 (11)0.0018 (10)
C270.0776 (19)0.0430 (14)0.087 (2)0.0012 (13)0.0119 (16)0.0205 (14)
C280.168 (4)0.072 (2)0.193 (5)0.010 (3)0.120 (4)0.046 (3)
Geometric parameters (Å, º) top
O11—C151.219 (3)C17—C181.479 (4)
O12—C161.193 (3)C21—C221.382 (3)
O13—C161.313 (3)C22—C231.393 (3)
O13—C171.458 (4)C25—C261.535 (3)
O21—C251.214 (3)C27—C281.441 (6)
O22—C261.188 (3)C11—H110.92 (2)
O23—C261.315 (3)C12—H121.03 (3)
O23—C271.467 (3)C17—H1710.97
N14—C131.424 (3)C17—H1720.97
N14—C151.338 (3)C18—H1810.96
N24—C231.414 (3)C18—H1820.96
N24—C251.351 (3)C18—H1830.96
N14—H140.81 (3)C21—H210.93 (3)
N24—H240.90 (2)C22—H221.02 (3)
C11—C121.379 (4)C27—H2710.97
C11—C211.367 (4)C27—H2720.97
C12—C131.395 (3)C28—H2810.96
C13—C231.389 (3)C28—H2820.96
C15—C161.528 (3)C28—H2830.96
O11···O132.679 (3)C15···O12ii3.347 (3)
O11···N242.722 (3)C16···C16ii3.354 (3)
O11···C233.125 (3)C16···O12ii3.207 (3)
O11···C21i3.248 (3)C17···O12iii3.109 (4)
O12···C15ii3.347 (3)C21···O11ix3.248 (3)
O12···C17iii3.109 (4)C22···O212.927 (3)
O12···N142.694 (3)C23···O113.125 (3)
O12···C16ii3.207 (3)C25···C12iv3.333 (4)
O13···O112.679 (3)C26···O22vi3.265 (3)
O21···O222.792 (3)C26···O22v3.354 (3)
O21···C222.927 (3)C11···H272ix3.0505
O21···C12iv3.359 (3)C15···H242.37 (3)
O21···N14iv3.115 (3)C25···H222.73 (2)
O22···C26v3.354 (3)C25···H14iv3.05 (2)
O22···C26vi3.265 (3)C25···H12iv2.98 (2)
O22···O22vi3.179 (3)C28···H1833.0093
O22···O22v3.098 (3)H11···O22x2.82 (3)
O22···O212.792 (3)H12···H142.45 (3)
O23···N242.612 (2)H12···O21iv2.79 (3)
O11···H241.93 (2)H12···C25iv2.98 (2)
O11···H21i2.49 (3)H12···O21x2.52 (3)
O12···H1722.5879H12···O22x2.83 (2)
O12···H1712.6791H14···O122.28 (2)
O12···H142.28 (2)H14···H122.45 (3)
O12···H172iii2.5237H14···O21iv2.37 (2)
O13···H21i2.86 (3)H14···C25iv3.05 (2)
O21···H222.44 (2)H21···O11ix2.49 (3)
O21···H12vii2.52 (3)H21···O13ix2.86 (3)
O21···H182viii2.7912H22···O212.44 (2)
O21···H12iv2.79 (3)H22···C252.73 (2)
O21···H14iv2.37 (2)H22···H182viii2.5743
O22···H11vii2.82 (3)H24···O111.93 (2)
O22···H12vii2.83 (2)H24···O232.21 (2)
O22···H2712.4540H24···N142.63 (2)
O23···H242.21 (2)H24···C152.37 (3)
N14···O122.694 (3)H171···O122.6791
N14···N242.878 (3)H172···O122.5879
N14···O21iv3.115 (3)H172···O12iii2.5237
N24···O232.612 (2)H182···O21xi2.7912
N24···O112.722 (3)H182···H22xi2.5743
N24···N142.878 (3)H183···C283.0093
N24···C153.004 (3)H183···H2832.4883
N14···H242.63 (2)H271···O222.4540
C12···O21iv3.359 (3)H271···H271v2.1426
C12···C25iv3.333 (4)H272···C11i3.0505
C15···N243.004 (3)H283···H1832.4883
C16—O13—C17115.6 (2)O23—C27—C28107.5 (3)
C26—O23—C27117.6 (2)C12—C11—H11122.1 (17)
C13—N14—C15127.0 (2)C21—C11—H11117.3 (17)
C23—N24—C25124.84 (18)C11—C12—H12122.8 (13)
C15—N14—H14114.2 (16)C13—C12—H12117.3 (13)
C13—N14—H14118.5 (16)O13—C17—H171109.9
C23—N24—H24116.4 (15)O13—C17—H172109.9
C25—N24—H24118.2 (14)C18—C17—H171109.9
C12—C11—C21120.6 (2)C18—C17—H172109.9
C11—C12—C13119.8 (3)H171—C17—H172108.5
N14—C13—C12117.1 (2)C17—C18—H181109.5
N14—C13—C23122.97 (17)C17—C18—H182109.5
C12—C13—C23119.8 (2)C17—C18—H183109.5
O11—C15—C16122.41 (18)H181—C18—H182109.5
N14—C15—C16111.75 (19)H181—C18—H183109.5
O11—C15—N14125.8 (2)H182—C18—H183109.5
O12—C16—O13125.8 (2)C11—C21—H21121.1 (17)
O12—C16—C15122.7 (2)C22—C21—H21118.5 (17)
O13—C16—C15111.5 (2)C21—C22—H22122.0 (12)
O13—C17—C18109.1 (3)C23—C22—H22117.6 (12)
C11—C21—C22120.1 (3)O23—C27—H271110.2
C21—C22—C23120.3 (3)O23—C27—H272110.2
N24—C23—C22120.5 (2)C28—C27—H271110.2
C13—C23—C22119.23 (19)C28—C27—H272110.2
N24—C23—C13120.27 (18)H271—C27—H272108.5
O21—C25—N24125.8 (2)C27—C28—H281109.5
O21—C25—C26119.8 (2)C27—C28—H282109.5
N24—C25—C26114.38 (19)C27—C28—H283109.5
O22—C26—C25122.0 (2)H281—C28—H282109.5
O23—C26—C25111.6 (2)H281—C28—H283109.5
O22—C26—O23126.4 (2)H282—C28—H283109.5
C17—O13—C16—O125.0 (3)C11—C12—C13—N14175.12 (19)
C17—O13—C16—C15174.8 (2)C12—C13—C23—N24178.68 (18)
C16—O13—C17—C18174.0 (3)C12—C13—C23—C221.3 (3)
C27—O23—C26—O222.7 (4)N14—C13—C23—C22176.97 (19)
C27—O23—C26—C25175.4 (2)N14—C13—C23—N243.0 (3)
C26—O23—C27—C28152.9 (3)N14—C15—C16—O13165.54 (18)
C15—N14—C13—C12135.6 (2)N14—C15—C16—O1214.2 (3)
C13—N14—C15—C16178.54 (19)O11—C15—C16—O1312.3 (3)
C13—N14—C15—O110.7 (4)O11—C15—C16—O12167.9 (2)
C15—N14—C13—C2348.6 (3)C11—C21—C22—C232.6 (3)
C23—N24—C25—O211.6 (4)C21—C22—C23—C133.0 (3)
C23—N24—C25—C26179.5 (2)C21—C22—C23—N24176.98 (19)
C25—N24—C23—C13140.9 (2)O21—C25—C26—O23157.8 (2)
C25—N24—C23—C2239.1 (3)N24—C25—C26—O22161.5 (2)
C12—C11—C21—C220.5 (3)O21—C25—C26—O2220.4 (4)
C21—C11—C12—C131.2 (3)N24—C25—C26—O2320.3 (3)
C11—C12—C13—C230.8 (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, z1/2; (vi) x, y+1, z; (vii) x1/2, y+1/2, z1/2; (viii) x1/2, y1/2, z; (ix) x+1/2, y1/2, 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···AD—HH···AD···AD—H···A
N14—H14···O120.81 (3)2.28 (2)2.694 (3)112.2 (19)
N24—H24···O110.90 (2)1.93 (2)2.722 (3)145 (2)
N24—H24···O230.90 (2)2.21 (2)2.612 (2)106.5 (17)
C22—H22···O211.02 (3)2.44 (2)2.927 (3)108.5 (16)
N14—H14···O21iv0.81 (3)2.37 (2)3.115 (3)153 (2)
C17—H172···O12iii0.972.523.109 (4)119
C21—H21···O11ix0.93 (3)2.49 (3)3.248 (3)140 (2)
C12—H12···O21x1.03 (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, y1/2, z+1/2; (x) x+1/2, y+1/2, z+1/2.
 

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