The title compound, C
10H
24N
2O
2, 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
CCDC reference: 624903
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (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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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
C10H24N2O2 | F(000) = 228 |
Mr = 204.31 | Dx = 1.159 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2yn | Cell parameters from 1583 reflections |
a = 4.6334 (13) Å | θ = 1.8–27.9° |
b = 5.4777 (14) Å | µ = 0.08 mm−1 |
c = 23.161 (2) Å | T = 113 K |
β = 95.336 (6)° | Block, colorless |
V = 585.3 (2) Å3 | 0.12 × 0.08 × 0.04 mm |
Z = 2 | |
Data collection top
Rigaku Saturn diffractometer | 1157 independent reflections |
Radiation source: rotating anode | 1035 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.049 |
Detector resolution: 7.31 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −6→6 |
Tmin = 0.979, Tmax = 0.997 | l = −28→28 |
5952 measured reflections | |
Refinement top
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H 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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.7120 (3) | 0.4794 (2) | 0.06698 (5) | 0.0182 (4) | |
N1 | 0.1924 (3) | 0.7782 (3) | 0.05198 (6) | 0.0137 (4) | |
C1 | 0.1077 (4) | 1.0171 (3) | 0.02653 (7) | 0.0146 (4) | |
H1A | 0.2817 | 1.1034 | 0.0153 | 0.018* | |
H1B | 0.0190 | 1.1181 | 0.0556 | 0.018* | |
C2 | 0.4039 (3) | 0.7978 (3) | 0.10352 (7) | 0.0137 (4) | |
H2 | 0.5534 | 0.9226 | 0.0960 | 0.016* | |
C3 | 0.2536 (4) | 0.8748 (3) | 0.15662 (7) | 0.0190 (4) | |
H3A | 0.1376 | 0.7357 | 0.1690 | 0.023* | |
H3B | 0.1179 | 1.0099 | 0.1454 | 0.023* | |
C4 | 0.4613 (4) | 0.9575 (4) | 0.20809 (8) | 0.0261 (5) | |
H4A | 0.3501 | 1.0022 | 0.2405 | 0.031* | |
H4B | 0.5722 | 1.0992 | 0.1967 | 0.031* | |
H4C | 0.5947 | 0.8241 | 0.2200 | 0.031* | |
C5 | 0.5502 (4) | 0.5510 (3) | 0.11319 (8) | 0.0162 (4) | |
H5A | 0.6813 | 0.5572 | 0.1494 | 0.019* | |
H5B | 0.4004 | 0.4260 | 0.1183 | 0.019* | |
H1 | 0.275 (4) | 0.688 (4) | 0.0254 (9) | 0.020 (5)* | |
H6 | 0.857 (5) | 0.578 (4) | 0.0655 (9) | 0.037 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0140 (7) | 0.0170 (7) | 0.0237 (7) | 0.0007 (5) | 0.0021 (5) | −0.0038 (5) |
N1 | 0.0146 (7) | 0.0130 (8) | 0.0136 (7) | 0.0027 (6) | 0.0009 (6) | −0.0017 (6) |
C1 | 0.0136 (9) | 0.0137 (9) | 0.0161 (9) | 0.0022 (7) | −0.0001 (7) | 0.0000 (7) |
C2 | 0.0121 (8) | 0.0147 (9) | 0.0140 (9) | −0.0002 (7) | −0.0010 (7) | −0.0007 (7) |
C3 | 0.0175 (9) | 0.0216 (10) | 0.0175 (9) | 0.0028 (8) | 0.0001 (7) | −0.0010 (8) |
C4 | 0.0290 (11) | 0.0291 (11) | 0.0194 (10) | 0.0025 (9) | −0.0009 (8) | −0.0052 (8) |
C5 | 0.0128 (8) | 0.0169 (9) | 0.0187 (9) | −0.0001 (7) | −0.0001 (7) | 0.0018 (7) |
Geometric parameters (Å, º) top
O1—C5 | 1.418 (2) | C2—H2 | 1.0000 |
O1—H6 | 0.87 (3) | C3—C4 | 1.529 (2) |
N1—C1 | 1.473 (2) | C3—H3A | 0.9900 |
N1—C2 | 1.476 (2) | C3—H3B | 0.9900 |
N1—H1 | 0.90 (2) | C4—H4A | 0.9800 |
C1—C1i | 1.521 (3) | C4—H4B | 0.9800 |
C1—H1A | 0.9900 | C4—H4C | 0.9800 |
C1—H1B | 0.9900 | C5—H5A | 0.9900 |
C2—C5 | 1.520 (2) | C5—H5B | 0.9900 |
C2—C3 | 1.528 (2) | | |
| | | |
C5—O1—H6 | 108.9 (16) | C2—C3—H3A | 108.7 |
C1—N1—C2 | 113.02 (13) | C4—C3—H3A | 108.7 |
C1—N1—H1 | 109.2 (12) | C2—C3—H3B | 108.7 |
C2—N1—H1 | 107.5 (12) | C4—C3—H3B | 108.7 |
N1—C1—C1i | 110.15 (17) | H3A—C3—H3B | 107.6 |
N1—C1—H1A | 109.6 | C3—C4—H4A | 109.5 |
C1i—C1—H1A | 109.6 | C3—C4—H4B | 109.5 |
N1—C1—H1B | 109.6 | H4A—C4—H4B | 109.5 |
C1i—C1—H1B | 109.6 | C3—C4—H4C | 109.5 |
H1A—C1—H1B | 108.1 | H4A—C4—H4C | 109.5 |
N1—C2—C5 | 107.95 (13) | H4B—C4—H4C | 109.5 |
N1—C2—C3 | 110.67 (13) | O1—C5—C2 | 113.24 (14) |
C5—C2—C3 | 110.94 (14) | O1—C5—H5A | 108.9 |
N1—C2—H2 | 109.1 | C2—C5—H5A | 108.9 |
C5—C2—H2 | 109.1 | O1—C5—H5B | 108.9 |
C3—C2—H2 | 109.1 | C2—C5—H5B | 108.9 |
C2—C3—C4 | 114.08 (15) | H5A—C5—H5B | 107.7 |
| | | |
C2—N1—C1—C1i | 179.49 (16) | C5—C2—C3—C4 | 73.85 (19) |
C1—N1—C2—C5 | −160.86 (14) | N1—C2—C5—O1 | 63.18 (17) |
C1—N1—C2—C3 | 77.56 (18) | C3—C2—C5—O1 | −175.42 (14) |
N1—C2—C3—C4 | −166.35 (15) | | |
Symmetry code: (i) −x, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.90 (2) | 2.33 (2) | 3.163 (2) | 152.9 (16) |
N1—H1···O1 | 0.90 (2) | 2.444 (19) | 2.9051 (19) | 112.1 (14) |
O1—H6···N1iii | 0.87 (3) | 1.95 (3) | 2.810 (2) | 172 (2) |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1, y, z. |