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The title compound, C10H24N2O2, was synthesized by N-alkyl­ation of 1,2-dichloro­ethane with racemic 2-amino-1-butanol. The mol­ecule lies on a crystallographic inversion center and the crystal structure is stabilized by inter­molecular O—H...N and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603457X/lh2166sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603457X/lh2166Isup2.hkl
Contains datablock I

CCDC reference: 624903

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.059
  • wR factor = 0.130
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

(R*,S*)-2,2'-(Ethane-1,2-diyldiimino)dibutan-1-ol top
Crystal data top
C10H24N2O2F(000) = 228
Mr = 204.31Dx = 1.159 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 1583 reflections
a = 4.6334 (13) Åθ = 1.8–27.9°
b = 5.4777 (14) ŵ = 0.08 mm1
c = 23.161 (2) ÅT = 113 K
β = 95.336 (6)°Block, colorless
V = 585.3 (2) Å30.12 × 0.08 × 0.04 mm
Z = 2
Data collection top
Rigaku Saturn
diffractometer
1157 independent reflections
Radiation source: rotating anode1035 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.049
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.8°
ω scansh = 55
Absorption correction: multi-scan
(Jacobson, 1998)
k = 66
Tmin = 0.979, Tmax = 0.997l = 2828
5952 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.20 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.1608P]
where P = (Fo2 + 2Fc2)/3
1157 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7120 (3)0.4794 (2)0.06698 (5)0.0182 (4)
N10.1924 (3)0.7782 (3)0.05198 (6)0.0137 (4)
C10.1077 (4)1.0171 (3)0.02653 (7)0.0146 (4)
H1A0.28171.10340.01530.018*
H1B0.01901.11810.05560.018*
C20.4039 (3)0.7978 (3)0.10352 (7)0.0137 (4)
H20.55340.92260.09600.016*
C30.2536 (4)0.8748 (3)0.15662 (7)0.0190 (4)
H3A0.13760.73570.16900.023*
H3B0.11791.00990.14540.023*
C40.4613 (4)0.9575 (4)0.20809 (8)0.0261 (5)
H4A0.35011.00220.24050.031*
H4B0.57221.09920.19670.031*
H4C0.59470.82410.22000.031*
C50.5502 (4)0.5510 (3)0.11319 (8)0.0162 (4)
H5A0.68130.55720.14940.019*
H5B0.40040.42600.11830.019*
H10.275 (4)0.688 (4)0.0254 (9)0.020 (5)*
H60.857 (5)0.578 (4)0.0655 (9)0.037 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0140 (7)0.0170 (7)0.0237 (7)0.0007 (5)0.0021 (5)0.0038 (5)
N10.0146 (7)0.0130 (8)0.0136 (7)0.0027 (6)0.0009 (6)0.0017 (6)
C10.0136 (9)0.0137 (9)0.0161 (9)0.0022 (7)0.0001 (7)0.0000 (7)
C20.0121 (8)0.0147 (9)0.0140 (9)0.0002 (7)0.0010 (7)0.0007 (7)
C30.0175 (9)0.0216 (10)0.0175 (9)0.0028 (8)0.0001 (7)0.0010 (8)
C40.0290 (11)0.0291 (11)0.0194 (10)0.0025 (9)0.0009 (8)0.0052 (8)
C50.0128 (8)0.0169 (9)0.0187 (9)0.0001 (7)0.0001 (7)0.0018 (7)
Geometric parameters (Å, º) top
O1—C51.418 (2)C2—H21.0000
O1—H60.87 (3)C3—C41.529 (2)
N1—C11.473 (2)C3—H3A0.9900
N1—C21.476 (2)C3—H3B0.9900
N1—H10.90 (2)C4—H4A0.9800
C1—C1i1.521 (3)C4—H4B0.9800
C1—H1A0.9900C4—H4C0.9800
C1—H1B0.9900C5—H5A0.9900
C2—C51.520 (2)C5—H5B0.9900
C2—C31.528 (2)
C5—O1—H6108.9 (16)C2—C3—H3A108.7
C1—N1—C2113.02 (13)C4—C3—H3A108.7
C1—N1—H1109.2 (12)C2—C3—H3B108.7
C2—N1—H1107.5 (12)C4—C3—H3B108.7
N1—C1—C1i110.15 (17)H3A—C3—H3B107.6
N1—C1—H1A109.6C3—C4—H4A109.5
C1i—C1—H1A109.6C3—C4—H4B109.5
N1—C1—H1B109.6H4A—C4—H4B109.5
C1i—C1—H1B109.6C3—C4—H4C109.5
H1A—C1—H1B108.1H4A—C4—H4C109.5
N1—C2—C5107.95 (13)H4B—C4—H4C109.5
N1—C2—C3110.67 (13)O1—C5—C2113.24 (14)
C5—C2—C3110.94 (14)O1—C5—H5A108.9
N1—C2—H2109.1C2—C5—H5A108.9
C5—C2—H2109.1O1—C5—H5B108.9
C3—C2—H2109.1C2—C5—H5B108.9
C2—C3—C4114.08 (15)H5A—C5—H5B107.7
C2—N1—C1—C1i179.49 (16)C5—C2—C3—C473.85 (19)
C1—N1—C2—C5160.86 (14)N1—C2—C5—O163.18 (17)
C1—N1—C2—C377.56 (18)C3—C2—C5—O1175.42 (14)
N1—C2—C3—C4166.35 (15)
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.90 (2)2.33 (2)3.163 (2)152.9 (16)
N1—H1···O10.90 (2)2.444 (19)2.9051 (19)112.1 (14)
O1—H6···N1iii0.87 (3)1.95 (3)2.810 (2)172 (2)
Symmetry codes: (ii) x+1, y+1, z; (iii) x+1, y, z.
 

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