N,N'-Bis(2-hydroxy­cyclo­hexyl)-trans-cyclo­hexane-1,2-di­amine: a structure reanalysed at low temperature

The title compound, C₁₈H₃₄N₂O₂, has been prepared and its solid-state structure redetermined at low temperature. The crystalline structure contains only RSSR and SRRS diastereo­meric pairs occurring in alternating layers within the crystal, reinforcing the idea that a high degree of diastereoselectivity is attained in the reaction of poly­amines and cyclo­hexene oxide. The compound crystallizes in space group C2/c and the molecule sits on a crystallographic twofold axis.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.131
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXTL (Bruker, 1999).

N,N'-bis(2-hydroxycyclohexyl)-trans-cyclohexane-1,2-diamine

Crystal data

C18H34N2O2	F(000) = 688
Mr = 310.47	Dx = 1.152 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 975 reflections
a = 11.8682 (17) Å	θ = 2.4–29.3°
b = 17.512 (3) Å	µ = 0.07 mm^−1
c = 10.2790 (15) Å	T = 123 K
β = 123.074 (2)°	Plate, colourless
V = 1790.2 (5) Å^3	0.40 × 0.34 × 0.12 mm
Z = 4

Data collection

Bruker SMART 1K CCD diffractometer	1514 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.5°, θmin = 2.3°
ω scans	h = −8→14
5446 measured reflections	k = −21→21
1852 independent reflections	l = −12→10

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0842P)^2 + 0.6514P] where P = (Fo^2 + 2Fc^2)/3
1852 reflections	(Δ/σ)max = 0.001
108 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.26 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
N1	0.87482 (11)	0.26213 (6)	0.24675 (12)	0.0180 (3)
H111	0.7916 (17)	0.2784 (9)	0.1813 (18)	0.028 (4)*
O1	1.11126 (8)	0.17741 (5)	0.47534 (10)	0.0233 (3)
H112	1.109 (2)	0.2033 (11)	0.389 (2)	0.059 (6)*
C1	0.97922 (12)	0.15161 (7)	0.42255 (14)	0.0190 (3)
H1	0.9483	0.1167	0.3321	0.023*
C2	0.87922 (12)	0.21767 (7)	0.37096 (13)	0.0181 (3)
H2	0.9082	0.2519	0.4618	0.022*
C3	0.74017 (13)	0.18527 (7)	0.31501 (15)	0.0213 (3)
H3A	0.6749	0.2277	0.2821	0.026*
H3B	0.7102	0.1519	0.2240	0.026*
C4	0.74285 (13)	0.13952 (7)	0.44323 (15)	0.0236 (3)
H4A	0.7644	0.1740	0.5302	0.028*
H4B	0.6528	0.1173	0.4025	0.028*
C5	0.84701 (14)	0.07554 (8)	0.50288 (16)	0.0255 (3)
H5A	0.8185	0.0370	0.4200	0.031*
H5B	0.8526	0.0501	0.5922	0.031*
C6	0.98533 (13)	0.10659 (7)	0.55290 (15)	0.0232 (3)
H6A	1.0189	0.1401	0.6446	0.028*
H6B	1.0491	0.0636	0.5832	0.028*
C7	0.96625 (12)	0.32917 (7)	0.29608 (14)	0.0181 (3)
H7	1.0381	0.3229	0.4086	0.022*
C8	0.89101 (13)	0.40360 (7)	0.27741 (15)	0.0216 (3)
H8A	0.8094	0.4060	0.1710	0.026*
H8B	0.8618	0.4035	0.3511	0.026*
C9	0.97674 (13)	0.47427 (7)	0.30632 (14)	0.0217 (3)
H9A	1.0558	0.4741	0.4147	0.026*
H9B	0.9236	0.5209	0.2908	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0131 (5)	0.0228 (6)	0.0163 (5)	−0.0008 (4)	0.0068 (4)	0.0009 (4)
O1	0.0152 (5)	0.0323 (6)	0.0207 (5)	0.0000 (4)	0.0086 (4)	0.0032 (4)
C1	0.0159 (6)	0.0231 (7)	0.0185 (6)	−0.0006 (5)	0.0097 (5)	−0.0015 (5)
C2	0.0172 (6)	0.0208 (6)	0.0175 (6)	−0.0007 (5)	0.0103 (5)	−0.0011 (4)
C3	0.0174 (6)	0.0231 (7)	0.0251 (6)	−0.0001 (5)	0.0126 (5)	−0.0014 (5)
C4	0.0246 (7)	0.0233 (7)	0.0295 (7)	−0.0031 (5)	0.0190 (6)	−0.0038 (5)
C5	0.0286 (8)	0.0231 (7)	0.0301 (7)	−0.0020 (6)	0.0194 (6)	0.0005 (5)
C6	0.0239 (7)	0.0241 (7)	0.0226 (7)	0.0011 (5)	0.0134 (6)	0.0017 (5)
C7	0.0150 (6)	0.0212 (6)	0.0168 (6)	−0.0014 (5)	0.0078 (5)	−0.0009 (4)
C8	0.0200 (7)	0.0243 (7)	0.0236 (6)	0.0003 (5)	0.0139 (5)	−0.0008 (5)
C9	0.0226 (7)	0.0213 (7)	0.0222 (6)	−0.0001 (5)	0.0129 (5)	−0.0017 (5)

Geometric parameters (Å, º)

N1—C2	1.4718 (15)	C4—H4B	0.9900
N1—C7	1.4874 (15)	C5—C6	1.5276 (18)
N1—H111	0.885 (17)	C5—H5A	0.9900
O1—C1	1.4234 (15)	C5—H5B	0.9900
O1—H112	0.99 (2)	C6—H6A	0.9900
C1—C6	1.5218 (17)	C6—H6B	0.9900
C1—C2	1.5301 (17)	C7—C8	1.5317 (17)
C1—H1	1.0000	C7—C7^i	1.539 (2)
C2—C3	1.5298 (17)	C7—H7	1.0000
C2—H2	1.0000	C8—C9	1.5250 (17)
C3—C4	1.5278 (18)	C8—H8A	0.9900
C3—H3A	0.9900	C8—H8B	0.9900
C3—H3B	0.9900	C9—C9^i	1.531 (2)
C4—C5	1.5271 (19)	C9—H9A	0.9900
C4—H4A	0.9900	C9—H9B	0.9900
C2—N1—C7	116.61 (9)	C4—C5—H5A	109.4
C2—N1—H111	109.0 (10)	C6—C5—H5A	109.4
C7—N1—H111	108.0 (10)	C4—C5—H5B	109.4
C1—O1—H112	108.5 (12)	C6—C5—H5B	109.4
O1—C1—C6	108.37 (10)	H5A—C5—H5B	108.0
O1—C1—C2	112.12 (10)	C1—C6—C5	111.22 (10)
C6—C1—C2	110.61 (10)	C1—C6—H6A	109.4
O1—C1—H1	108.6	C5—C6—H6A	109.4
C6—C1—H1	108.6	C1—C6—H6B	109.4
C2—C1—H1	108.6	C5—C6—H6B	109.4
N1—C2—C3	110.47 (10)	H6A—C6—H6B	108.0
N1—C2—C1	110.74 (9)	N1—C7—C8	111.22 (10)
C3—C2—C1	108.87 (10)	N1—C7—C7^i	108.55 (8)
N1—C2—H2	108.9	C8—C7—C7^i	112.75 (8)
C3—C2—H2	108.9	N1—C7—H7	108.1
C1—C2—H2	108.9	C8—C7—H7	108.1
C4—C3—C2	111.09 (10)	C7^i—C7—H7	108.1
C4—C3—H3A	109.4	C9—C8—C7	112.64 (10)
C2—C3—H3A	109.4	C9—C8—H8A	109.1
C4—C3—H3B	109.4	C7—C8—H8A	109.1
C2—C3—H3B	109.4	C9—C8—H8B	109.1
H3A—C3—H3B	108.0	C7—C8—H8B	109.1
C5—C4—C3	111.25 (10)	H8A—C8—H8B	107.8
C5—C4—H4A	109.4	C8—C9—C9^i	109.29 (9)
C3—C4—H4A	109.4	C8—C9—H9A	109.8
C5—C4—H4B	109.4	C9^i—C9—H9A	109.8
C3—C4—H4B	109.4	C8—C9—H9B	109.8
H4A—C4—H4B	108.0	C9^i—C9—H9B	109.8
C4—C5—C6	111.08 (11)	H9A—C9—H9B	108.3
C7—N1—C2—C3	146.80 (10)	O1—C1—C6—C5	−178.75 (10)
C7—N1—C2—C1	−92.50 (12)	C2—C1—C6—C5	57.97 (13)
O1—C1—C2—N1	57.93 (12)	C4—C5—C6—C1	−54.68 (14)
C6—C1—C2—N1	179.02 (9)	C2—N1—C7—C8	−99.60 (12)
O1—C1—C2—C3	179.58 (9)	C2—N1—C7—C7^i	135.80 (11)
C6—C1—C2—C3	−59.33 (12)	N1—C7—C8—C9	−172.39 (9)
N1—C2—C3—C4	−179.51 (9)	C7^i—C7—C8—C9	−50.19 (16)
C1—C2—C3—C4	58.67 (13)	C7—C8—C9—C9^i	58.23 (15)
C2—C3—C4—C5	−56.49 (14)	C8—C7—C7^i—C8^i	45.3 (2)
C3—C4—C5—C6	53.77 (14)	N1—C7—C7^i—N1^i	−67.27 (17)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H111···O1^ii	0.885 (17)	2.172 (17)	3.0273 (14)	162.2 (14)
O1—H112···N1^i	0.99 (2)	1.82 (2)	2.8021 (14)	170.3 (17)
C8—H8A···O1^ii	0.99	2.56	3.3800 (16)	140

Symmetry codes: (i) −x+2, y, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2.