Diethyl N,N'-(p-phenylene)dioxamate.

In the crystal structure, the mol-ecule of the title compound, C(14)H(16)N(2)O(6), is located on an inversion centre. The amide -NHCO- plane makes a dihedral angle of 34.08 (9)° with the benzene ring. The mol-ecules are connected via inter-molecular 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.

Related 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

C14H16N2O6

M = 308.29

Monoclinic,

a = 11.328 (5) Å

b = 7.769 (5) Å

c = 8.372 (5) Å

β = 95.566 (5)°

V = 733.3 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 295 (2) K

0.3 × 0.2 × 0.1 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 2003 ▶) T min = 0.975, T max = 0.989

5037 measured reflections

1285 independent reflections

1075 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.00

1285 reflections

104 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027190/is2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027190/is2327Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H16N2O6	F000 = 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 = 2.2–27.0º
b = 7.769 (5) Å	µ = 0.11 mm−1
c = 8.372 (5) Å	T = 295 (2) K
β = 95.566 (5)º	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)
Monochromator: graphite	Rint = 0.017
T = 295(2) K	θmax = 25.0º
ω scans	θmin = 1.8º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0715P)2 + 0.3357P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.022
1285 reflections	Δρmax = 0.33 e Å−3
104 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) .