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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048884/bh2060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048884/bh2060Isup2.hkl
Contains datablock I

CCDC reference: 629431

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

Computing details top

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 top
Crystal data top
C10H20N2O4F(000) = 252
Mr = 232.28Dx = 1.235 Mg m3
Monoclinic, P21/nMelting point: 385.2 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 5.029 (1) ÅCell parameters from 4225 reflections
b = 23.674 (5) Åθ = 3.4–27.5°
c = 5.2550 (11) ŵ = 0.10 mm1
β = 93.56 (3)°T = 293 K
V = 624.4 (2) Å3Plate, colourless
Z = 20.32 × 0.22 × 0.09 mm
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
1432 independent reflections
Radiation source: rotating anode1023 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 66
Tmin = 0.970, Tmax = 0.991k = 3030
6072 measured reflectionsl = 66
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046Only H-atom coordinates refined
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.0675P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
1432 reflectionsΔρmax = 0.13 e Å3
114 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.055 (16)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.7790 (2)0.12437 (5)0.5670 (3)0.0532 (4)
H1D0.620 (4)0.1315 (7)0.606 (3)0.064*
O10.8910 (2)0.18616 (5)0.8688 (2)0.0629 (4)
O21.2114 (2)0.14174 (6)0.6695 (3)0.0774 (5)
C11.0899 (5)0.21685 (11)1.0195 (5)0.0783 (6)
H1A1.150 (13)0.251 (3)0.910 (12)0.117*0.53 (4)
H1B1.266 (15)0.200 (2)1.039 (14)0.117*0.53 (4)
H1C1.016 (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)
C20.9798 (3)0.14966 (6)0.6983 (3)0.0480 (4)
C30.8295 (3)0.08099 (7)0.3823 (3)0.0544 (4)
H3A0.927 (3)0.0494 (7)0.470 (3)0.065*
H3B0.951 (4)0.0943 (7)0.264 (3)0.065*
C40.5770 (3)0.05978 (7)0.2470 (3)0.0522 (4)
H4A0.493 (3)0.0901 (7)0.152 (3)0.063*
H4B0.454 (3)0.0482 (7)0.370 (3)0.063*
C50.6252 (3)0.01175 (7)0.0669 (3)0.0512 (4)
H5A0.719 (3)0.0187 (7)0.158 (3)0.061*
H5B0.738 (3)0.0236 (7)0.057 (3)0.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0382 (6)0.0586 (7)0.0628 (8)0.0020 (5)0.0016 (5)0.0157 (6)
O10.0540 (6)0.0675 (7)0.0667 (7)0.0007 (5)0.0011 (5)0.0227 (5)
O20.0392 (6)0.0997 (10)0.0929 (10)0.0008 (5)0.0005 (5)0.0348 (7)
C10.0788 (14)0.0812 (14)0.0741 (14)0.0173 (12)0.0017 (11)0.0290 (11)
C20.0428 (7)0.0484 (7)0.0526 (8)0.0023 (6)0.0002 (6)0.0042 (6)
C30.0433 (8)0.0593 (9)0.0602 (10)0.0025 (7)0.0012 (6)0.0125 (7)
C40.0425 (8)0.0583 (9)0.0554 (9)0.0023 (6)0.0004 (6)0.0077 (7)
C50.0407 (7)0.0575 (8)0.0552 (9)0.0021 (6)0.0020 (6)0.0074 (7)
Geometric parameters (Å, º) top
N1—C21.3294 (18)C1—H1C'0.99 (7)
N1—C31.4463 (19)C3—C41.503 (2)
N1—H1D0.855 (19)C3—H3A0.994 (17)
O1—C21.3408 (17)C3—H3B0.954 (18)
O1—C11.434 (2)C4—C51.509 (2)
O2—C21.1987 (18)C4—H4A0.955 (17)
C1—H1A1.04 (6)C4—H4B0.962 (18)
C1—H1B0.97 (7)C5—C5i1.510 (3)
C1—H1C0.92 (7)C5—H5A0.970 (17)
C1—H1A'0.96 (8)C5—H5B0.935 (18)
C1—H1B'1.06 (7)
C2—N1—C3120.59 (12)H1A'—C1—H1C'105 (5)
C2—N1—H1D118.4 (12)H1B'—C1—H1C'116 (5)
C3—N1—H1D120.6 (12)O2—C2—N1125.22 (14)
C2—O1—C1116.48 (14)O2—C2—O1123.46 (13)
O1—C1—H1A107 (3)N1—C2—O1111.32 (12)
O1—C1—H1B117 (3)N1—C3—C4112.11 (12)
H1A—C1—H1B94 (4)N1—C3—H3A108.9 (10)
O1—C1—H1C109 (3)C4—C3—H3A110.3 (9)
H1A—C1—H1C108 (4)N1—C3—H3B110.5 (10)
H1B—C1—H1C119 (5)C4—C3—H3B111.0 (10)
O1—C1—H1A'115 (4)H3A—C3—H3B103.7 (13)
H1A—C1—H1A'49 (4)C3—C4—C5112.62 (12)
H1B—C1—H1A'47 (4)C3—C4—H4A109.1 (10)
H1C—C1—H1A'134 (5)C5—C4—H4A108.8 (10)
O1—C1—H1B'111 (3)C3—C4—H4B109.8 (10)
H1A—C1—H1B'139 (4)C5—C4—H4B110.0 (10)
H1B—C1—H1B'57 (4)H4A—C4—H4B106.3 (14)
H1C—C1—H1B'70 (4)C4—C5—C5i114.08 (15)
H1A'—C1—H1B'102 (5)C4—C5—H5A110.2 (10)
O1—C1—H1C'108 (3)C5i—C5—H5A108.6 (9)
H1A—C1—H1C'61 (4)C4—C5—H5B109.9 (10)
H1B—C1—H1C'134 (5)C5i—C5—H5B108.1 (10)
H1C—C1—H1C'50 (4)H5A—C5—H5B105.5 (14)
C3—N1—C2—O24.0 (2)C2—N1—C3—C4177.45 (14)
C3—N1—C2—O1176.56 (13)N1—C3—C4—C5176.07 (14)
C1—O1—C2—O20.5 (2)C3—C4—C5—C5i178.36 (17)
C1—O1—C2—N1178.97 (17)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O2ii0.855 (19)2.116 (19)2.9664 (17)172.9 (17)
Symmetry code: (ii) x1, y, z.
 

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