(1R,2R)-N,N′-Bis[1-(2-pyrid­yl)ethyl­idene]cyclo­hexane-1,2-diamine

Saleh Salga, M.; Khaledi, H.; Mohd Ali, H.; Puteh, R.

doi:10.1107/S1600536810013607

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1095

https://doi.org/10.1107/S1600536810013607

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(1R,2R)-N,N′-Bis[1-(2-pyridyl)ethylidene]cyclohexane-1,2-diamine

Muhammad Saleh Salga,^a Hamid Khaledi,^a ^* Hapipah Mohd Ali ^a and Rustam Puteh ^b

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Physics, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@perdana.um.edu.my

(Received 7 April 2010; accepted 13 April 2010; online 17 April 2010)

In the title compound, C₂₀H₂₄N₄, the cyclohexane ring adopts a chair conformation with the two imine groups linked at equatorial positions. The two halves of the molecule are related by a crystallographic twofold rotation axis. The dihedral angle between the pyridine rings is 75.73 (3)°.

Related literature

For the crystal structures of some Schiff bases derived from cyclohexane-1,2-diamine, see: Aslantaş et al. (2007 ); Glidewell et al. (2005 ); Liu et al. (2006 ).

Experimental

Crystal data

C₂₀H₂₄N₄
M_r = 320.43
Monoclinic, C 2/c
a = 18.0605 (3) Å
b = 8.9371 (1) Å
c = 11.1076 (2) Å
β = 97.970 (1)°
V = 1775.54 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.49 × 0.37 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.975
8186 measured reflections
2044 independent reflections
1833 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.121
S = 1.06
2044 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810013607/pv2274sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013607/pv2274Isup2.hkl

checkCIF report

Comment top

The stucture of the title compound is presented in Fig. 1. The cyclohexane ring adopts a chair conformation with the two imines linked at equatorial positions. The two halves of the molecule are realted by a two-fold rotation. The dihedral angel between the two pyridine rings is 75.73 (3)°. The crystal structure is devoid of any inter- or intra- molecular interactions.

The bond distances and angles in the title molecule are in agreement with the corresponding bond distances and angles reported in some related structures (Aslantaş et al., 2007; Glidewell et al., 2005; Liu et al., 2006).

Related literature top

For the crystal structures of some Schiff bases derived from cyclohexane-1,2-diamine, see: Aslantaş et al. (2007); Glidewell et al. (2005); Liu et al. (2006).

Experimental top

A mixture of 2-acetylpyiridine (0.444 g, 4 mmol) and 1,2-diaminocyclohexane (0.224, 2 mmol) was refluxed in ethanol (50 ml) for 2 hours. The solution was then set aside overnight whereupon the yellow crystals of the title compound were formed.

Structure description top

For the crystal structures of some Schiff bases derived from cyclohexane-1,2-diamine, see: Aslantaş et al. (2007); Glidewell et al. (2005); Liu et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot of the title compound at 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code for the unlabeled atoms: -x, y, -z+3/2.

(1R,2R)-N,N'-Bis[1-(2- pyridyl)ethylidene]cyclohexane-1,2-diamine top

Crystal data top

C₂₀H₂₄N₄	F(000) = 688
M_r = 320.43	D_x = 1.199 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4367 reflections
a = 18.0605 (3) Å	θ = 2.3–30.3°
b = 8.9371 (1) Å	µ = 0.07 mm⁻¹
c = 11.1076 (2) Å	T = 100 K
β = 97.970 (1)°	Block, pale yellow
V = 1775.54 (5) Å³	0.49 × 0.37 × 0.35 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2044 independent reflections
Radiation source: fine-focus sealed tube	1833 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→22
T_min = 0.965, T_max = 0.975	k = −11→11
8186 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0714P)² + 1.0614P] where P = (F_o² + 2F_c²)/3
2044 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₂₄N₄	V = 1775.54 (5) Å³
M_r = 320.43	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.0605 (3) Å	µ = 0.07 mm⁻¹
b = 8.9371 (1) Å	T = 100 K
c = 11.1076 (2) Å	0.49 × 0.37 × 0.35 mm
β = 97.970 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2044 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1833 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.975	R_int = 0.019
8186 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
2044 reflections	Δρ_min = −0.23 e Å⁻³
110 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	U_iso*/U_eq
N1	0.07952 (5)	0.04557 (10)	0.74621 (8)	0.0160 (2)
N2	0.19413 (5)	0.35854 (10)	0.82811 (8)	0.0188 (2)
C1	0.22757 (6)	0.47046 (13)	0.77554 (10)	0.0214 (3)
H1	0.2635	0.5294	0.8252	0.026*
C2	0.21265 (6)	0.50475 (13)	0.65292 (10)	0.0212 (3)
H2	0.2368	0.5865	0.6199	0.025*
C3	0.16173 (7)	0.41697 (13)	0.57979 (10)	0.0233 (3)
H3	0.1504	0.4372	0.4953	0.028*
C4	0.12752 (6)	0.29891 (12)	0.63160 (10)	0.0208 (3)
H4	0.0929	0.2362	0.5831	0.025*
C5	0.14487 (6)	0.27409 (11)	0.75622 (9)	0.0154 (2)
C6	0.10752 (6)	0.14970 (11)	0.81635 (9)	0.0160 (2)
C7	0.10754 (7)	0.16392 (14)	0.95159 (10)	0.0269 (3)
H7A	0.0734	0.2443	0.9679	0.040*
H7B	0.1582	0.1873	0.9909	0.040*
H7C	0.0910	0.0694	0.9838	0.040*
C8	0.03861 (5)	−0.08031 (11)	0.78929 (9)	0.0151 (2)
H8	0.0327	−0.0650	0.8766	0.018*
C9	0.08258 (6)	−0.22419 (11)	0.77538 (9)	0.0169 (2)
H9A	0.0978	−0.2272	0.6931	0.020*
H9B	0.1285	−0.2242	0.8354	0.020*
C10	0.03633 (6)	−0.36338 (12)	0.79419 (10)	0.0188 (3)
H10A	0.0656	−0.4542	0.7812	0.023*
H10B	0.0248	−0.3653	0.8787	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0176 (4)	0.0139 (4)	0.0170 (4)	−0.0002 (3)	0.0038 (3)	0.0006 (3)
N2	0.0187 (5)	0.0183 (5)	0.0191 (4)	−0.0021 (3)	0.0020 (3)	−0.0008 (3)
C1	0.0197 (5)	0.0199 (6)	0.0239 (5)	−0.0045 (4)	0.0007 (4)	−0.0011 (4)
C2	0.0208 (5)	0.0178 (5)	0.0253 (6)	−0.0030 (4)	0.0040 (4)	0.0038 (4)
C3	0.0283 (6)	0.0224 (6)	0.0186 (5)	−0.0045 (4)	0.0011 (4)	0.0038 (4)
C4	0.0244 (6)	0.0186 (5)	0.0184 (5)	−0.0052 (4)	0.0002 (4)	0.0000 (4)
C5	0.0154 (5)	0.0127 (5)	0.0184 (5)	0.0017 (4)	0.0039 (4)	−0.0007 (4)
C6	0.0155 (5)	0.0157 (5)	0.0173 (5)	0.0013 (4)	0.0039 (4)	0.0001 (4)
C7	0.0362 (7)	0.0279 (6)	0.0176 (5)	−0.0114 (5)	0.0075 (5)	−0.0030 (4)
C8	0.0179 (5)	0.0134 (5)	0.0140 (4)	−0.0012 (4)	0.0027 (4)	0.0004 (4)
C9	0.0176 (5)	0.0152 (5)	0.0179 (5)	0.0008 (4)	0.0023 (4)	0.0010 (4)
C10	0.0215 (6)	0.0136 (5)	0.0211 (5)	0.0015 (4)	0.0020 (4)	0.0019 (4)

Geometric parameters (Å, º) top

N1—C6	1.2726 (14)	C6—C7	1.5075 (15)
N1—C8	1.4623 (12)	C7—H7A	0.9800
N2—C5	1.3422 (14)	C7—H7B	0.9800
N2—C1	1.3432 (14)	C7—H7C	0.9800
C1—C2	1.3856 (16)	C8—C9	1.5304 (14)
C1—H1	0.9500	C8—C8ⁱ	1.5392 (19)
C2—C3	1.3833 (16)	C8—H8	1.0000
C2—H2	0.9500	C9—C10	1.5288 (14)
C3—C4	1.3874 (15)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.3940 (15)	C10—C10ⁱ	1.526 (2)
C4—H4	0.9500	C10—H10A	0.9900
C5—C6	1.5039 (14)	C10—H10B	0.9900

C6—N1—C8	122.56 (9)	H7A—C7—H7B	109.5
C5—N2—C1	117.45 (9)	C6—C7—H7C	109.5
N2—C1—C2	123.65 (10)	H7A—C7—H7C	109.5
N2—C1—H1	118.2	H7B—C7—H7C	109.5
C2—C1—H1	118.2	N1—C8—C9	108.70 (8)
C3—C2—C1	118.33 (10)	N1—C8—C8ⁱ	105.88 (7)
C3—C2—H2	120.8	C9—C8—C8ⁱ	112.63 (6)
C1—C2—H2	120.8	N1—C8—H8	109.8
C2—C3—C4	119.06 (10)	C9—C8—H8	109.8
C2—C3—H3	120.5	C8ⁱ—C8—H8	109.8
C4—C3—H3	120.5	C10—C9—C8	111.64 (8)
C3—C4—C5	118.76 (10)	C10—C9—H9A	109.3
C3—C4—H4	120.6	C8—C9—H9A	109.3
C5—C4—H4	120.6	C10—C9—H9B	109.3
N2—C5—C4	122.72 (10)	C8—C9—H9B	109.3
N2—C5—C6	116.91 (9)	H9A—C9—H9B	108.0
C4—C5—C6	120.37 (9)	C10ⁱ—C10—C9	110.46 (7)
N1—C6—C5	115.68 (9)	C10ⁱ—C10—H10A	109.6
N1—C6—C7	128.08 (10)	C9—C10—H10A	109.6
C5—C6—C7	116.23 (9)	C10ⁱ—C10—H10B	109.6
C6—C7—H7A	109.5	C9—C10—H10B	109.6
C6—C7—H7B	109.5	H10A—C10—H10B	108.1

Symmetry code: (i) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₄
M_r	320.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.0605 (3), 8.9371 (1), 11.1076 (2)
β (°)	97.970 (1)
V (Å³)	1775.54 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.49 × 0.37 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	8186, 2044, 1833
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.121, 1.06
No. of reflections	2044
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C).

References

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