(1R,2R)-N,N'-Bis[1-(2-pyrid-yl)ethyl-idene]cyclo-hexane-1,2-diamine.

In the title compound, C(20)H(24)N(4), the cyclo-hexane ring adopts a chair conformation with the two imine groups linked at equatorial positions. The two halves of the mol-ecule 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 = 320.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.06

2044 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013607/pv2274Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H24N4	F(000) = 688
Mr = 320.43	Dx = 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

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

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(Fo2) + (0.0714P)2 + 1.0614P] where P = (Fo2 + 2Fc2)/3
2044 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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