3-Oxapentane-1,5-diyl dicarbamate.

The complete mol-ecule of the title compound, C(6)H(12)N(2)O(5), is generated by a rotation about a twofold axis. The conformation along the bond sequence linking the two amino groups is trans-trans-(+)gauche-trans-trans. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional supra-molecular architecture.

Related literature

For self-assembled mono-layers of alkyl carbamate and alkyl dicarbamate, see: Kim et al. (2003 ▶, 2005a ▶,b ▶). For the synthesis of the title compound, see: Sidney et al. (1965 ▶); Takeuchi & Ninagawa (1971 ▶); Takeuchi (1974 ▶). For a closely related structure and background references, see: Xia et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C6H12N2O5

M = 192.18

Monoclinic,

a = 14.263 (4) Å

b = 5.1412 (15) Å

c = 12.276 (4) Å

β = 99.393 (5)°

V = 888.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 294 K

0.30 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.983

2358 measured reflections

904 independent reflections

748 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.084

S = 1.06

904 reflections

69 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.14 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011981/tk5072sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011981/tk5072Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011981/tk5072Isup3.cml

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

C6H12N2O5	F(000) = 408
Mr = 192.18	Dx = 1.437 Mg m−3
Monoclinic, C2/c	Melting point: 428 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.263 (4) Å	Cell parameters from 1304 reflections
b = 5.1412 (15) Å	θ = 3.4–26.0°
c = 12.276 (4) Å	µ = 0.13 mm−1
β = 99.393 (5)°	T = 294 K
V = 888.1 (5) Å3	Plate, colourless
Z = 4	0.30 × 0.20 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	904 independent reflections
Radiation source: fine-focus sealed tube	748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
Tmin = 0.960, Tmax = 0.983	k = −6→6
2358 measured reflections	l = −8→15

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.3363P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
904 reflections	Δρmax = 0.16 e Å−3
69 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (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	0.25476 (6)	0.5124 (2)	0.40946 (8)	0.0461 (3)
O2	0.39925 (5)	0.69845 (18)	0.42131 (7)	0.0374 (3)
O3	0.5000	0.8767 (2)	0.2500	0.0358 (3)
N1	0.37706 (8)	0.3841 (3)	0.53985 (10)	0.0451 (3)
H1A	0.3429 (12)	0.260 (3)	0.5619 (13)	0.054 (4)*
H1B	0.4360 (12)	0.398 (3)	0.5657 (13)	0.051 (4)*
C1	0.33731 (8)	0.5279 (2)	0.45456 (10)	0.0333 (3)
C2	0.35837 (8)	0.8634 (3)	0.33006 (11)	0.0392 (3)
H2A	0.3086	0.9708	0.3518	0.047*
H2B	0.3306	0.7572	0.2678	0.047*
C3	0.43501 (9)	1.0321 (3)	0.29804 (11)	0.0379 (3)
H3A	0.4071	1.1628	0.2455	0.045*
H3B	0.4683	1.1206	0.3628	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0300 (5)	0.0575 (6)	0.0477 (6)	−0.0091 (4)	−0.0029 (4)	0.0107 (5)
O2	0.0266 (4)	0.0479 (5)	0.0365 (5)	−0.0039 (4)	0.0020 (4)	0.0091 (4)
O3	0.0363 (6)	0.0328 (6)	0.0403 (7)	0.000	0.0128 (5)	0.000
N1	0.0301 (6)	0.0570 (8)	0.0464 (7)	−0.0046 (5)	0.0007 (5)	0.0168 (6)
C1	0.0277 (6)	0.0402 (7)	0.0321 (6)	−0.0025 (5)	0.0055 (5)	−0.0009 (5)
C2	0.0309 (6)	0.0480 (8)	0.0386 (7)	0.0031 (5)	0.0050 (5)	0.0089 (6)
C3	0.0376 (7)	0.0365 (7)	0.0414 (7)	0.0034 (5)	0.0119 (6)	0.0027 (5)

O1—C1	1.2191 (15)	N1—H1B	0.852 (17)
O2—C1	1.3543 (15)	C2—C3	1.4973 (18)
O2—C2	1.4494 (15)	C2—H2A	0.9700
O3—C3	1.4228 (14)	C2—H2B	0.9700
O3—C3i	1.4228 (14)	C3—H3A	0.9700
N1—C1	1.3305 (17)	C3—H3B	0.9700
N1—H1A	0.872 (18)
C1—O2—C2	114.33 (9)	C3—C2—H2A	109.9
C3—O3—C3i	111.63 (13)	O2—C2—H2B	109.9
C1—N1—H1A	117.6 (10)	C3—C2—H2B	109.9
C1—N1—H1B	121.0 (11)	H2A—C2—H2B	108.3
H1A—N1—H1B	120.9 (15)	O3—C3—C2	109.65 (11)
O1—C1—N1	125.25 (12)	O3—C3—H3A	109.7
O1—C1—O2	122.31 (11)	C2—C3—H3A	109.7
N1—C1—O2	112.44 (11)	O3—C3—H3B	109.7
O2—C2—C3	108.85 (10)	C2—C3—H3B	109.7
O2—C2—H2A	109.9	H3A—C3—H3B	108.2
C2—O2—C1—O1	1.42 (17)	C3i—O3—C3—C2	170.41 (12)
C2—O2—C1—N1	−178.66 (11)	O2—C2—C3—O3	68.67 (13)
C1—O2—C2—C3	−177.18 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.872 (18)	2.046 (18)	2.9086 (17)	169.9 (14)
N1—H1B···O2iii	0.852 (17)	2.381 (17)	3.1763 (17)	155.6 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.872 (18)	2.046 (18)	2.9086 (17)	169.9 (14)
N1—H1B⋯O2ii	0.852 (17)	2.381 (17)	3.1763 (17)	155.6 (14)

Symmetry codes: (i) ; (ii) .