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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3399
https://doi.org/10.1107/S1600536811049038

cis-N1,N2-Bis(2-hy­dr­oxy­benzyl­­idene)cyclo­hexane-1,2-di­amine

Ping Fan,a Chunhua Ge,a* Xiangdong Zhang,a Rui Zhanga and Su Lia

aCollege of Chemistry, Liaoning University, Shenyang, Liaoning 110036, People's Republic of China
*Correspondence e-mail: chhge@lnu.edu.cn

(Received 9 November 2011; accepted 17 November 2011; online 23 November 2011)

In the title compound, C20H22N2O2, the cyclo­hexane ring adopts a chair conformation and the two N atoms bonded to salicyl­idene groups are in cis positions. Both hy­droxy groups are involved in intra­molecular O—H⋯N hydrogen bonding and the two benzene rings form a dihedral angle of 60.5 (1)°.

Related literature

For the crystal structure of trans-N,N′-bis­(salicyl­idene)-1,2-cyclo­hexa­nediamine, see: Cannadine et al. (1996[Cannadine, J. C., Corden, J. P., Errington, W., Moore, P. & Wallbridge, M. G. H. (1996). Acta Cryst. C52, 1014-1017.]); Liu et al. (1997[Liu, Q., Ding, M., Lin, Y. & Xing, Y. (1997). Acta Cryst. C53, 1671-1673.]), and for the crystal structures of its complexes, see: Khalaji et al. (2010[Khalaji, A. D., Hadadzadeh, H., Fejfarova, K. & Dusek, M. (2010). Polyhedron, 29, 807-812.]); Man et al. (2008[Man, W.-L., Kwong, H.-K., Lam, W. W. Y., Xiang, J., Wong, T.-W., Lam, W.-H., Wong, W.-T., Peng, S.-M. & Lau, T.-C. (2008). Inorg. Chem. 47, 5936-5944.]); Xu et al. (2009[Xu, Z., Zhou, M.-D., Drees, M., Chaffey-Millar, H., Herdtweck, E., Herrmann, W. A. & Kuhn, F. E. (2009). Inorg. Chem. 48, 6812-6822.]).

[Scheme 1]

Experimental

Crystal data

  • C20H22N2O2

  • Mr = 322.40

  • Orthorhombic, P 21 21 21

  • a = 6.125 (3) Å

  • b = 13.763 (6) Å

  • c = 21.537 (9) Å

  • V = 1815.4 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.25 × 0.15 × 0.12 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.987, Tmax = 0.991

  • 9439 measured reflections

  • 4195 independent reflections

  • 2178 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.115

  • S = 0.99

  • 4195 reflections

  • 219 parameters

  • H-atom parameters constrained

  • Δρmax = 0.09 e Å−3

  • Δρmin = −0.10 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.87 2.599 (3) 148
O2—H2⋯N2 0.82 1.84 2.577 (3) 148

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049038/cv5199sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049038/cv5199Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049038/cv5199Isup3.cml

checkCIF report


Comment top

1,2-Cyclohexanediamine has trans-cis isomers, so their reaction products are also isomers. trans-N,N'-Bis(salicylidene)-1,2-cyclohexanediamine has been prepared and characterized via X-ray crystallography (Cannadine et al., 1996; Liu et al., 1997). The compound is current of interest due to its fascinating versatility as coordination ligand (Khalaji et al., 2010; Man et al., 2008; Xu et al., 2009). As cis-isomer is difficult to form complex, it has received relatively few studies.

The stucture of the title compound is shown in Fig. 1. The two N-salicylidene groups are cis in the structure with the same constitution but differ in the arrangement of their atoms in space. Dihedral angel between aromatic rings is 60.5 (1) °, between the ring of C1—C6 and C8/C10/C12 is 88.8 (1) °, between the ring of C15—C20 and C8/C10/C12 is 75.2 (1)°, respectively. hydroxy groups and imine groups are involved in intramolecular hydrogen bonding (Table 1).

Related literature top

For the crystal structure of trans-N,N'-bis(salicylidene)-1,2-cyclohexanediamine, see: Cannadine et al. (1996); Liu et al. (1997), and for the crystal structures of its complexes, see: Khalaji et al. (2010); Man et al. (2008); Xu et al. (2009).

Experimental top

The cis-trans mixture of 1,2-cyclohexanediamine was purchased from Alfa Aesar and was used as received without further purification. The title compound was obtained as following: added 0.05 mol salicylaldehyde slowly to ethanol solution of 1,2-cyclohexanediamine with stirring, then the resulting mixture was stirred 2 h under reflexing. By slow evaporation, yellow block-shape single crystals suitable for X-ray analysis were obtained within several days.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.93 - 0.97 Å, and O—H = 0.82 Å), and refined in a riding model, with Uiso(H) = 1.2-1.5 Ueq of the parent atom. In the absence of any significant anomalous scatterers in the molecule, the 1621 Friedel pairs were merged before the final refinement.

Structure description top

1,2-Cyclohexanediamine has trans-cis isomers, so their reaction products are also isomers. trans-N,N'-Bis(salicylidene)-1,2-cyclohexanediamine has been prepared and characterized via X-ray crystallography (Cannadine et al., 1996; Liu et al., 1997). The compound is current of interest due to its fascinating versatility as coordination ligand (Khalaji et al., 2010; Man et al., 2008; Xu et al., 2009). As cis-isomer is difficult to form complex, it has received relatively few studies.

The stucture of the title compound is shown in Fig. 1. The two N-salicylidene groups are cis in the structure with the same constitution but differ in the arrangement of their atoms in space. Dihedral angel between aromatic rings is 60.5 (1) °, between the ring of C1—C6 and C8/C10/C12 is 88.8 (1) °, between the ring of C15—C20 and C8/C10/C12 is 75.2 (1)°, respectively. hydroxy groups and imine groups are involved in intramolecular hydrogen bonding (Table 1).

For the crystal structure of trans-N,N'-bis(salicylidene)-1,2-cyclohexanediamine, see: Cannadine et al. (1996); Liu et al. (1997), and for the crystal structures of its complexes, see: Khalaji et al. (2010); Man et al. (2008); Xu et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
2-(N-{2-[(2-hydroxybenzylidene)amino]cyclohexyl}carboximidoyl)phenol top
Crystal data top
C20H22N2O2F(000) = 688
Mr = 322.40Dx = 1.180 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 126 reflections
a = 6.125 (3) Åθ = 2.5–23.1°
b = 13.763 (6) ŵ = 0.08 mm−1
c = 21.537 (9) ÅT = 296 K
V = 1815.4 (13) Å3Block, yellow
Z = 40.25 × 0.15 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4195 independent reflections
Radiation source: fine-focus sealed tube2178 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 28.2°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −8→8
Tmin = 0.987, Tmax = 0.991k = −18→8
9439 measured reflectionsl = −27→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0487P)2]
where P = (Fo2 + 2Fc2)/3
4195 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.09 e Å−3
0 restraintsΔρmin = −0.10 e Å−3
Crystal data top
C20H22N2O2V = 1815.4 (13) Å3
Mr = 322.40Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.125 (3) ŵ = 0.08 mm−1
b = 13.763 (6) ÅT = 296 K
c = 21.537 (9) Å0.25 × 0.15 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4195 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2178 reflections with I > 2σ(I)
Tmin = 0.987, Tmax = 0.991Rint = 0.026
9439 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 0.99Δρmax = 0.09 e Å−3
4195 reflectionsΔρmin = −0.10 e Å−3
219 parameters
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
xyzUiso*/Ueq
N2−0.0052 (3)1.09660 (12)0.07839 (9)0.0732 (5)
N1−0.0383 (3)0.92191 (11)0.14663 (8)0.0654 (4)
C14−0.0964 (4)1.13716 (14)0.03205 (11)0.0692 (6)
H14−0.23111.16720.03740.083*
O10.3379 (3)0.84294 (11)0.17057 (9)0.0955 (5)
H10.23970.88330.17220.143*
C150.0042 (3)1.13768 (13)−0.02904 (10)0.0622 (5)
C7−0.0724 (4)0.85231 (15)0.10808 (9)0.0642 (5)
H7−0.20200.85210.08560.077*
C13−0.1099 (4)1.09759 (15)0.13967 (10)0.0736 (6)
H13−0.22941.14490.13880.088*
C200.2131 (4)1.09706 (15)−0.03864 (11)0.0699 (6)
O20.3257 (3)1.05667 (15)0.00898 (8)0.1061 (6)
H20.25201.05930.04070.159*
C8−0.2060 (3)0.99701 (14)0.15462 (9)0.0670 (6)
H8−0.32640.98380.12580.080*
C16−0.1018 (4)1.17840 (16)−0.07974 (12)0.0803 (7)
H16−0.23791.2071−0.07420.096*
C50.0343 (4)0.69815 (16)0.05699 (9)0.0795 (7)
H5−0.09730.69840.03550.095*
C10.2831 (4)0.77194 (15)0.12906 (11)0.0720 (6)
C60.0818 (4)0.77415 (14)0.09806 (9)0.0635 (6)
C190.3026 (4)1.09673 (16)−0.09734 (12)0.0848 (7)
H190.43971.0695−0.10380.102*
C17−0.0095 (5)1.17723 (17)−0.13826 (12)0.0919 (8)
H17−0.08351.2042−0.17180.110*
C30.3740 (6)0.62313 (19)0.07855 (15)0.1027 (9)
H30.47210.57260.07190.123*
C20.4287 (4)0.69612 (18)0.11904 (13)0.0940 (8)
H2A0.56210.69490.13960.113*
C180.1903 (5)1.13633 (16)−0.14639 (13)0.0882 (7)
H180.25211.1351−0.18580.106*
C9−0.2941 (4)0.99545 (17)0.22072 (10)0.0861 (7)
H9A−0.41961.03820.22340.103*
H9B−0.34270.93020.23060.103*
C40.1800 (6)0.62283 (17)0.04797 (13)0.0955 (9)
H40.14540.57220.02110.115*
C120.0551 (5)1.13028 (19)0.18700 (12)0.1004 (8)
H12A0.10161.19600.17740.120*
H12B0.18221.08840.18500.120*
C10−0.1265 (5)1.0268 (2)0.26770 (11)0.1056 (9)
H10A−0.00670.98070.26800.127*
H10B−0.19181.02720.30870.127*
C11−0.0396 (6)1.1276 (2)0.25261 (13)0.1206 (10)
H11A0.07291.14510.28230.145*
H11B−0.15681.17470.25600.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0736 (12)0.0638 (10)0.0823 (12)0.0124 (10)0.0150 (11)0.0022 (10)
N10.0665 (11)0.0612 (10)0.0686 (10)0.0021 (9)−0.0040 (9)−0.0028 (9)
C140.0631 (14)0.0491 (11)0.0953 (16)0.0074 (10)0.0081 (14)−0.0095 (11)
O10.0795 (11)0.0822 (10)0.1249 (12)0.0047 (10)−0.0239 (11)−0.0169 (10)
C150.0558 (12)0.0503 (11)0.0807 (14)−0.0014 (10)0.0059 (12)−0.0102 (10)
C70.0657 (14)0.0729 (13)0.0540 (11)−0.0063 (12)0.0026 (11)0.0031 (11)
C130.0736 (15)0.0627 (12)0.0846 (15)0.0136 (11)0.0117 (14)−0.0044 (12)
C200.0635 (14)0.0615 (12)0.0848 (16)0.0066 (11)0.0056 (14)−0.0014 (12)
O20.0858 (12)0.1315 (14)0.1009 (12)0.0447 (11)0.0156 (11)0.0126 (12)
C80.0585 (13)0.0764 (13)0.0662 (13)0.0082 (12)−0.0002 (11)−0.0029 (11)
C160.0686 (15)0.0780 (14)0.0943 (17)0.0114 (12)−0.0031 (15)−0.0093 (14)
C50.1023 (19)0.0715 (14)0.0649 (13)−0.0134 (15)0.0107 (14)−0.0049 (11)
C10.0746 (16)0.0562 (12)0.0850 (16)−0.0052 (12)0.0086 (14)0.0037 (12)
C60.0739 (16)0.0567 (12)0.0600 (12)−0.0067 (12)0.0075 (12)0.0038 (10)
C190.0761 (16)0.0802 (15)0.0980 (18)0.0085 (14)0.0251 (16)−0.0053 (14)
C170.104 (2)0.0924 (17)0.0795 (17)0.0148 (16)−0.0074 (17)−0.0083 (14)
C30.116 (3)0.0641 (16)0.128 (2)0.0091 (17)0.046 (2)0.0023 (16)
C20.0843 (18)0.0730 (15)0.125 (2)0.0094 (15)0.0115 (17)0.0144 (16)
C180.104 (2)0.0741 (15)0.0870 (18)0.0034 (16)0.0185 (17)−0.0029 (13)
C90.0863 (17)0.0986 (16)0.0734 (15)0.0124 (15)0.0108 (14)0.0039 (13)
C40.133 (3)0.0620 (15)0.0916 (19)−0.0111 (18)0.037 (2)−0.0087 (13)
C120.101 (2)0.0944 (18)0.1055 (19)−0.0143 (16)0.0050 (17)−0.0323 (14)
C100.115 (2)0.133 (2)0.0689 (15)0.028 (2)−0.0044 (17)−0.0073 (16)
C110.122 (2)0.145 (3)0.0947 (19)−0.005 (2)−0.0084 (19)−0.0495 (19)
Geometric parameters (Å, º) top
N2—C141.273 (3)C5—H50.9300
N2—C131.467 (3)C1—C21.390 (3)
N1—C71.285 (2)C1—C61.402 (3)
N1—C81.467 (2)C19—C181.373 (3)
C14—C151.453 (3)C19—H190.9300
C14—H140.9300C17—C181.359 (4)
O1—C11.366 (2)C17—H170.9300
O1—H10.8200C3—C41.358 (4)
C15—C161.389 (3)C3—C21.372 (4)
C15—C201.411 (3)C3—H30.9300
C7—C61.448 (3)C2—H2A0.9300
C7—H70.9300C18—H180.9300
C13—C121.504 (3)C9—C101.504 (4)
C13—C81.538 (3)C9—H9A0.9700
C13—H130.9800C9—H9B0.9700
C20—O21.355 (2)C4—H40.9300
C20—C191.378 (3)C12—C111.528 (4)
O2—H20.8200C12—H12A0.9700
C8—C91.523 (3)C12—H12B0.9700
C8—H80.9800C10—C111.522 (4)
C16—C171.382 (3)C10—H10A0.9700
C16—H160.9300C10—H10B0.9700
C5—C41.381 (4)C11—H11A0.9700
C5—C61.400 (3)C11—H11B0.9700
C14—N2—C13120.62 (18)C18—C19—H19119.8
C7—N1—C8119.17 (18)C20—C19—H19119.8
N2—C14—C15121.72 (19)C18—C17—C16119.4 (3)
N2—C14—H14119.1C18—C17—H17120.3
C15—C14—H14119.1C16—C17—H17120.3
C1—O1—H1109.5C4—C3—C2121.6 (3)
C16—C15—C20118.0 (2)C4—C3—H3119.2
C16—C15—C14121.0 (2)C2—C3—H3119.2
C20—C15—C14121.0 (2)C3—C2—C1119.5 (3)
N1—C7—C6123.0 (2)C3—C2—H2A120.3
N1—C7—H7118.5C1—C2—H2A120.3
C6—C7—H7118.5C17—C18—C19121.1 (2)
N2—C13—C12108.59 (19)C17—C18—H18119.5
N2—C13—C8110.31 (16)C19—C18—H18119.5
C12—C13—C8112.61 (19)C10—C9—C8112.5 (2)
N2—C13—H13108.4C10—C9—H9A109.1
C12—C13—H13108.4C8—C9—H9A109.1
C8—C13—H13108.4C10—C9—H9B109.1
O2—C20—C19119.4 (2)C8—C9—H9B109.1
O2—C20—C15120.8 (2)H9A—C9—H9B107.8
C19—C20—C15119.7 (2)C3—C4—C5119.6 (3)
C20—O2—H2109.5C3—C4—H4120.2
N1—C8—C9110.34 (17)C5—C4—H4120.2
N1—C8—C13109.95 (16)C13—C12—C11111.4 (2)
C9—C8—C13110.13 (17)C13—C12—H12A109.3
N1—C8—H8108.8C11—C12—H12A109.3
C9—C8—H8108.8C13—C12—H12B109.3
C13—C8—H8108.8C11—C12—H12B109.3
C17—C16—C15121.4 (2)H12A—C12—H12B108.0
C17—C16—H16119.3C9—C10—C11110.9 (2)
C15—C16—H16119.3C9—C10—H10A109.5
C4—C5—C6121.0 (3)C11—C10—H10A109.5
C4—C5—H5119.5C9—C10—H10B109.5
C6—C5—H5119.5C11—C10—H10B109.5
O1—C1—C2118.7 (2)H10A—C10—H10B108.1
O1—C1—C6120.8 (2)C10—C11—C12110.6 (2)
C2—C1—C6120.4 (2)C10—C11—H11A109.5
C5—C6—C1117.9 (2)C12—C11—H11A109.5
C5—C6—C7120.9 (2)C10—C11—H11B109.5
C1—C6—C7121.2 (2)C12—C11—H11B109.5
C18—C19—C20120.4 (2)H11A—C11—H11B108.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.599 (3)148
O2—H2···N20.821.842.577 (3)148

Experimental details

Crystal data
Chemical formulaC20H22N2O2
Mr322.40
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)6.125 (3), 13.763 (6), 21.537 (9)
V (Å3)1815.4 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.25 × 0.15 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.987, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		9439, 4195, 2178
Rint0.026
(sin θ/λ)max (Å−1)0.664
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.115, 0.99
No. of reflections4195
No. of parameters219
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.09, −0.10

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.599 (3)148
O2—H2···N20.821.842.577 (3)148
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 20971062 and 21171081).

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3399
https://doi.org/10.1107/S1600536811049038
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