Dimethyl N,N′-(hexane-1,6-di­yl)dicarbamate

The mol­ecule of the title compound, C₁₀H₂₀N₂O₄, lies on an inversion centre. The crystal structure is stabilized by inter­molecular N—H...O classical hydrogen bonds, which pack the mol­ecules along the short [100] axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.127
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT390_ALERT_3_C Deviating Methyl C1      X-C-H Bond Angle ......     117.00 Deg.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 199a7); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Dimethyl N,N'-(hexane-1,6-diyl)dicarbamate

Crystal data

C10H20N2O4	F(000) = 252
Mr = 232.28	Dx = 1.235 Mg m^−3
Monoclinic, P21/n	Melting point: 385.2 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.029 (1) Å	Cell parameters from 4225 reflections
b = 23.674 (5) Å	θ = 3.4–27.5°
c = 5.2550 (11) Å	µ = 0.10 mm^−1
β = 93.56 (3)°	T = 293 K
V = 624.4 (2) Å^3	Plate, colourless
Z = 2	0.32 × 0.22 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer	1432 independent reflections
Radiation source: rotating anode	1023 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.970, Tmax = 0.991	k = −30→30
6072 measured reflections	l = −6→6

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	Only H-atom coordinates refined
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.0675P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
1432 reflections	Δρmax = 0.13 e Å^−3
114 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (16)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.7790 (2)	0.12437 (5)	0.5670 (3)	0.0532 (4)
H1D	0.620 (4)	0.1315 (7)	0.606 (3)	0.064*
O1	0.8910 (2)	0.18616 (5)	0.8688 (2)	0.0629 (4)
O2	1.2114 (2)	0.14174 (6)	0.6695 (3)	0.0774 (5)
C1	1.0899 (5)	0.21685 (11)	1.0195 (5)	0.0783 (6)
H1A	1.150 (13)	0.251 (3)	0.910 (12)	0.117*	0.53 (4)
H1B	1.266 (15)	0.200 (2)	1.039 (14)	0.117*	0.53 (4)
H1C	1.016 (12)	0.231 (3)	1.161 (12)	0.117*	0.53 (4)
H1A'	1.253 (16)	0.223 (3)	0.938 (14)	0.117*	0.47 (4)
H1B'	1.157 (14)	0.194 (3)	1.184 (14)	0.117*	0.47 (4)
H1C'	1.019 (13)	0.255 (3)	1.052 (16)	0.117*	0.47 (4)
C2	0.9798 (3)	0.14966 (6)	0.6983 (3)	0.0480 (4)
C3	0.8295 (3)	0.08099 (7)	0.3823 (3)	0.0544 (4)
H3A	0.927 (3)	0.0494 (7)	0.470 (3)	0.065*
H3B	0.951 (4)	0.0943 (7)	0.264 (3)	0.065*
C4	0.5770 (3)	0.05978 (7)	0.2470 (3)	0.0522 (4)
H4A	0.493 (3)	0.0901 (7)	0.152 (3)	0.063*
H4B	0.454 (3)	0.0482 (7)	0.370 (3)	0.063*
C5	0.6252 (3)	0.01175 (7)	0.0669 (3)	0.0512 (4)
H5A	0.719 (3)	−0.0187 (7)	0.158 (3)	0.061*
H5B	0.738 (3)	0.0236 (7)	−0.057 (3)	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0382 (6)	0.0586 (7)	0.0628 (8)	0.0020 (5)	0.0016 (5)	−0.0157 (6)
O1	0.0540 (6)	0.0675 (7)	0.0667 (7)	−0.0007 (5)	0.0011 (5)	−0.0227 (5)
O2	0.0392 (6)	0.0997 (10)	0.0929 (10)	0.0008 (5)	0.0005 (5)	−0.0348 (7)
C1	0.0788 (14)	0.0812 (14)	0.0741 (14)	−0.0173 (12)	−0.0017 (11)	−0.0290 (11)
C2	0.0428 (7)	0.0484 (7)	0.0526 (8)	0.0023 (6)	−0.0002 (6)	−0.0042 (6)
C3	0.0433 (8)	0.0593 (9)	0.0602 (10)	0.0025 (7)	0.0012 (6)	−0.0125 (7)
C4	0.0425 (8)	0.0583 (9)	0.0554 (9)	0.0023 (6)	−0.0004 (6)	−0.0077 (7)
C5	0.0407 (7)	0.0575 (8)	0.0552 (9)	0.0021 (6)	0.0020 (6)	−0.0074 (7)

Geometric parameters (Å, º)

N1—C2	1.3294 (18)	C1—H1C'	0.99 (7)
N1—C3	1.4463 (19)	C3—C4	1.503 (2)
N1—H1D	0.855 (19)	C3—H3A	0.994 (17)
O1—C2	1.3408 (17)	C3—H3B	0.954 (18)
O1—C1	1.434 (2)	C4—C5	1.509 (2)
O2—C2	1.1987 (18)	C4—H4A	0.955 (17)
C1—H1A	1.04 (6)	C4—H4B	0.962 (18)
C1—H1B	0.97 (7)	C5—C5^i	1.510 (3)
C1—H1C	0.92 (7)	C5—H5A	0.970 (17)
C1—H1A'	0.96 (8)	C5—H5B	0.935 (18)
C1—H1B'	1.06 (7)
C2—N1—C3	120.59 (12)	H1A'—C1—H1C'	105 (5)
C2—N1—H1D	118.4 (12)	H1B'—C1—H1C'	116 (5)
C3—N1—H1D	120.6 (12)	O2—C2—N1	125.22 (14)
C2—O1—C1	116.48 (14)	O2—C2—O1	123.46 (13)
O1—C1—H1A	107 (3)	N1—C2—O1	111.32 (12)
O1—C1—H1B	117 (3)	N1—C3—C4	112.11 (12)
H1A—C1—H1B	94 (4)	N1—C3—H3A	108.9 (10)
O1—C1—H1C	109 (3)	C4—C3—H3A	110.3 (9)
H1A—C1—H1C	108 (4)	N1—C3—H3B	110.5 (10)
H1B—C1—H1C	119 (5)	C4—C3—H3B	111.0 (10)
O1—C1—H1A'	115 (4)	H3A—C3—H3B	103.7 (13)
H1A—C1—H1A'	49 (4)	C3—C4—C5	112.62 (12)
H1B—C1—H1A'	47 (4)	C3—C4—H4A	109.1 (10)
H1C—C1—H1A'	134 (5)	C5—C4—H4A	108.8 (10)
O1—C1—H1B'	111 (3)	C3—C4—H4B	109.8 (10)
H1A—C1—H1B'	139 (4)	C5—C4—H4B	110.0 (10)
H1B—C1—H1B'	57 (4)	H4A—C4—H4B	106.3 (14)
H1C—C1—H1B'	70 (4)	C4—C5—C5^i	114.08 (15)
H1A'—C1—H1B'	102 (5)	C4—C5—H5A	110.2 (10)
O1—C1—H1C'	108 (3)	C5^i—C5—H5A	108.6 (9)
H1A—C1—H1C'	61 (4)	C4—C5—H5B	109.9 (10)
H1B—C1—H1C'	134 (5)	C5^i—C5—H5B	108.1 (10)
H1C—C1—H1C'	50 (4)	H5A—C5—H5B	105.5 (14)
C3—N1—C2—O2	4.0 (2)	C2—N1—C3—C4	−177.45 (14)
C3—N1—C2—O1	−176.56 (13)	N1—C3—C4—C5	−176.07 (14)
C1—O1—C2—O2	0.5 (2)	C3—C4—C5—C5^i	178.36 (17)
C1—O1—C2—N1	−178.97 (17)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2^ii	0.855 (19)	2.116 (19)	2.9664 (17)	172.9 (17)

Symmetry code: (ii) x−1, y, z.