1,4-Phenyl-enebis(methyl-ene) dicarbamate.

The title compound, C(10)H(12)N(2)O(4), is a phenyl dicarbamate with crystallographically imposed inversion symmetry. The dihedral angle between the carbamo-yloxy plane [i.e. the plane of the N-C(O)-O fragment; r.m.s. deviation = 0.002 (3) Å] and the plane of the aryl ring is 29.2 (1)°. In the crystal, two different centrosymmetric N-H⋯O hydrogen-bond inter-actions are observed; these are described as R(2) (2)(8) and R(2) (4)(8) in graph-set notation. The rings form an alternating sequence, linking the mol-ecules into a sheet structure parallel to (011).

Related literature

For self-assembled monolayers of alkyl carbamate and alkyl dicarbamate, see: Kim et al. (2003 ▶); Kim et al. (2005a ▶,b ▶). For the synthesis of the title compound, see: Takeuchi et al. (1971 ▶, 1974 ▶).

Experimental

Crystal data

C10H12N2O4

M = 224.22

Triclinic,

a = 4.9542 (14) Å

b = 6.4194 (18) Å

c = 8.418 (2) Å

α = 79.290 (4)°

β = 79.351 (4)°

γ = 88.640 (4)°

V = 258.50 (13) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.30 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.975

1310 measured reflections

902 independent reflections

764 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.06

902 reflections

81 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: Mercury and SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012718/nk2147sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012718/nk2147Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812012718/nk2147Isup4.cdx

Supplementary material file. DOI: 10.1107/S1600536812012718/nk2147Isup4.cml

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

C10H12N2O4	Z = 1
Mr = 224.22	F(000) = 118
Triclinic, P1	Dx = 1.440 Mg m−3
Hall symbol: -P 1	Melting point: 485 K
a = 4.9542 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.4194 (18) Å	Cell parameters from 819 reflections
c = 8.418 (2) Å	θ = 2.5–26.1°
α = 79.290 (4)°	µ = 0.11 mm−1
β = 79.351 (4)°	T = 294 K
γ = 88.640 (4)°	Needle, colourless
V = 258.50 (13) Å3	0.30 × 0.28 × 0.22 mm

Bruker SMART CCD area-detector diffractometer	902 independent reflections
Radiation source: fine-focus sealed tube	764 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→5
Tmin = 0.962, Tmax = 0.975	k = −7→5
1310 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.0526P] where P = (Fo2 + 2Fc2)/3
902 reflections	(Δ/σ)max < 0.001
81 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	0.2931 (2)	0.76540 (17)	0.12334 (15)	0.0498 (4)
O2	0.5723 (2)	0.51407 (16)	0.22471 (13)	0.0427 (4)
N1	0.7519 (3)	0.7787 (2)	0.02862 (18)	0.0451 (4)
C1	0.5223 (3)	0.6939 (2)	0.12480 (18)	0.0361 (4)
C2	0.3389 (3)	0.4099 (2)	0.3354 (2)	0.0419 (4)
H2A	0.1959	0.3894	0.2749	0.050*
H2B	0.2661	0.4963	0.4162	0.050*
C3	0.4273 (3)	0.1990 (2)	0.41993 (17)	0.0348 (4)
C4	0.6516 (3)	0.0921 (2)	0.35056 (19)	0.0432 (4)
H4	0.7555	0.1532	0.2496	0.052*
C5	0.2772 (3)	0.1045 (2)	0.57031 (19)	0.0417 (4)
H5	0.1262	0.1741	0.6189	0.050*
H1A	0.912 (4)	0.735 (3)	0.053 (2)	0.057 (5)*
H1B	0.740 (4)	0.914 (3)	−0.031 (2)	0.054 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0332 (7)	0.0417 (7)	0.0668 (8)	0.0023 (5)	−0.0147 (5)	0.0152 (5)
O2	0.0355 (6)	0.0318 (6)	0.0531 (7)	0.0018 (4)	−0.0082 (5)	0.0120 (5)
N1	0.0345 (8)	0.0387 (8)	0.0538 (8)	0.0008 (6)	−0.0088 (6)	0.0135 (6)
C1	0.0359 (8)	0.0287 (8)	0.0421 (8)	0.0007 (6)	−0.0127 (6)	0.0029 (6)
C2	0.0373 (9)	0.0350 (9)	0.0468 (9)	0.0009 (6)	−0.0043 (7)	0.0060 (7)
C3	0.0364 (8)	0.0291 (8)	0.0373 (8)	−0.0008 (6)	−0.0086 (6)	−0.0001 (6)
C4	0.0470 (10)	0.0375 (9)	0.0368 (8)	0.0027 (7)	0.0021 (7)	0.0042 (6)
C5	0.0417 (9)	0.0348 (8)	0.0432 (9)	0.0071 (7)	−0.0005 (7)	−0.0013 (7)

O1—C1	1.2163 (19)	C2—H2B	0.9700
O2—C1	1.3430 (17)	C3—C5	1.383 (2)
O2—C2	1.4348 (18)	C3—C4	1.386 (2)
N1—C1	1.331 (2)	C4—C5i	1.384 (2)
N1—H1A	0.88 (2)	C4—H4	0.9300
N1—H1B	0.93 (2)	C5—C4i	1.384 (2)
C2—C3	1.503 (2)	C5—H5	0.9300
C2—H2A	0.9700
C1—O2—C2	116.37 (12)	C3—C2—H2B	109.9
C1—N1—H1A	119.3 (12)	H2A—C2—H2B	108.3
C1—N1—H1B	116.7 (11)	C5—C3—C4	118.33 (14)
H1A—N1—H1B	118.9 (16)	C5—C3—C2	119.38 (14)
O1—C1—N1	125.38 (14)	C4—C3—C2	122.27 (14)
O1—C1—O2	123.02 (14)	C5i—C4—C3	120.78 (15)
N1—C1—O2	111.59 (13)	C5i—C4—H4	119.6
O2—C2—C3	108.74 (12)	C3—C4—H4	119.6
O2—C2—H2A	109.9	C3—C5—C4i	120.89 (15)
C3—C2—H2A	109.9	C3—C5—H5	119.6
O2—C2—H2B	109.9	C4i—C5—H5	119.6
C2—O2—C1—O1	−1.5 (2)	C5—C3—C4—C5i	0.2 (3)
C2—O2—C1—N1	179.38 (13)	C2—C3—C4—C5i	−178.21 (15)
C1—O2—C2—C3	172.41 (12)	C4—C3—C5—C4i	−0.2 (3)
O2—C2—C3—C5	156.37 (14)	C2—C3—C5—C4i	178.25 (15)
O2—C2—C3—C4	−25.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.88 (2)	2.11 (2)	2.930 (2)	155.6 (17)
N1—H1B···O1iii	0.93 (2)	2.07 (2)	2.9888 (19)	169.8 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88 (2)	2.11 (2)	2.930 (2)	155.6 (17)
N1—H1B⋯O1ii	0.93 (2)	2.07 (2)	2.9888 (19)	169.8 (16)

Symmetry codes: (i) ; (ii) .