(R,S)-2,2′-(Ethane-1,2-diyldiimino)dibutan-1-ol

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.

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

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

Crystal data

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) Å^3	0.12 × 0.08 × 0.04 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.1608P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C1^i	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—C1^i	110.15 (17)	H3A—C3—H3B	107.6
N1—C1—H1A	109.6	C3—C4—H4A	109.5
C1^i—C1—H1A	109.6	C3—C4—H4B	109.5
N1—C1—H1B	109.6	H4A—C4—H4B	109.5
C1^i—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—C1^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^ii	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···N1^iii	0.87 (3)	1.95 (3)	2.810 (2)	172 (2)

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1, y, z.