cis-N,N-Bis(2-hy-droxy-benzyl-idene)cyclo-hexane-1,2-diamine.

In the title compound, C(20)H(22)N(2)O(2), the cyclo-hexane ring adopts a chair conformation and the two N atoms bonded to salicyl-idene groups are in cis positions. Both hy-droxy groups are involved in intra-molecular 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 ▶); Liu et al. (1997 ▶), and for the crystal structures of its complexes, see: Khalaji et al. (2010 ▶); n class="Species">Man et al. (2008 ▶); Xu et al. (2009 ▶).

Experimental

Crystal data

C20H22N2O2

M = 322.40

Orthorhombic,

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 ▶) T min = 0.987, T max = 0.991

9439 measured reflections

4195 independent reflections

2178 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 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

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049038/cv5199sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049038/cv5199Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049038/cv5199Isup3.cml

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

C20H22N2O2	F(000) = 688
Mr = 322.40	Dx = 1.180 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 126 reflections
a = 6.125 (3) Å	θ = 2.5–23.1°
b = 13.763 (6) Å	µ = 0.08 mm−1
c = 21.537 (9) Å	T = 296 K
V = 1815.4 (13) Å3	Block, yellow
Z = 4	0.25 × 0.15 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	4195 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.987, Tmax = 0.991	k = −18→8
9439 measured reflections	l = −27→28

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-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 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.10 e Å−3

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.

	x	y	z	Uiso*/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	−0.2311	1.1672	0.0374	0.083*
O1	0.3379 (3)	0.84294 (11)	0.17057 (9)	0.0955 (5)
H1	0.2397	0.8833	0.1722	0.143*
C15	0.0042 (3)	1.13768 (13)	−0.02904 (10)	0.0622 (5)
C7	−0.0724 (4)	0.85231 (15)	0.10808 (9)	0.0642 (5)
H7	−0.2020	0.8521	0.0856	0.077*
C13	−0.1099 (4)	1.09759 (15)	0.13967 (10)	0.0736 (6)
H13	−0.2294	1.1449	0.1388	0.088*
C20	0.2131 (4)	1.09706 (15)	−0.03864 (11)	0.0699 (6)
O2	0.3257 (3)	1.05667 (15)	0.00898 (8)	0.1061 (6)
H2	0.2520	1.0593	0.0407	0.159*
C8	−0.2060 (3)	0.99701 (14)	0.15462 (9)	0.0670 (6)
H8	−0.3264	0.9838	0.1258	0.080*
C16	−0.1018 (4)	1.17840 (16)	−0.07974 (12)	0.0803 (7)
H16	−0.2379	1.2071	−0.0742	0.096*
C5	0.0343 (4)	0.69815 (16)	0.05699 (9)	0.0795 (7)
H5	−0.0973	0.6984	0.0355	0.095*
C1	0.2831 (4)	0.77194 (15)	0.12906 (11)	0.0720 (6)
C6	0.0818 (4)	0.77415 (14)	0.09806 (9)	0.0635 (6)
C19	0.3026 (4)	1.09673 (16)	−0.09734 (12)	0.0848 (7)
H19	0.4397	1.0695	−0.1038	0.102*
C17	−0.0095 (5)	1.17723 (17)	−0.13826 (12)	0.0919 (8)
H17	−0.0835	1.2042	−0.1718	0.110*
C3	0.3740 (6)	0.62313 (19)	0.07855 (15)	0.1027 (9)
H3	0.4721	0.5726	0.0719	0.123*
C2	0.4287 (4)	0.69612 (18)	0.11904 (13)	0.0940 (8)
H2A	0.5621	0.6949	0.1396	0.113*
C18	0.1903 (5)	1.13633 (16)	−0.14639 (13)	0.0882 (7)
H18	0.2521	1.1351	−0.1858	0.106*
C9	−0.2941 (4)	0.99545 (17)	0.22072 (10)	0.0861 (7)
H9A	−0.4196	1.0382	0.2234	0.103*
H9B	−0.3427	0.9302	0.2306	0.103*
C4	0.1800 (6)	0.62283 (17)	0.04797 (13)	0.0955 (9)
H4	0.1454	0.5722	0.0211	0.115*
C12	0.0551 (5)	1.13028 (19)	0.18700 (12)	0.1004 (8)
H12A	0.1016	1.1960	0.1774	0.120*
H12B	0.1822	1.0884	0.1850	0.120*
C10	−0.1265 (5)	1.0268 (2)	0.26770 (11)	0.1056 (9)
H10A	−0.0067	0.9807	0.2680	0.127*
H10B	−0.1918	1.0272	0.3087	0.127*
C11	−0.0396 (6)	1.1276 (2)	0.25261 (13)	0.1206 (10)
H11A	0.0729	1.1451	0.2823	0.145*
H11B	−0.1568	1.1747	0.2560	0.145*

	U11	U22	U33	U12	U13	U23
N2	0.0736 (12)	0.0638 (10)	0.0823 (12)	0.0124 (10)	0.0150 (11)	0.0022 (10)
N1	0.0665 (11)	0.0612 (10)	0.0686 (10)	0.0021 (9)	−0.0040 (9)	−0.0028 (9)
C14	0.0631 (14)	0.0491 (11)	0.0953 (16)	0.0074 (10)	0.0081 (14)	−0.0095 (11)
O1	0.0795 (11)	0.0822 (10)	0.1249 (12)	0.0047 (10)	−0.0239 (11)	−0.0169 (10)
C15	0.0558 (12)	0.0503 (11)	0.0807 (14)	−0.0014 (10)	0.0059 (12)	−0.0102 (10)
C7	0.0657 (14)	0.0729 (13)	0.0540 (11)	−0.0063 (12)	0.0026 (11)	0.0031 (11)
C13	0.0736 (15)	0.0627 (12)	0.0846 (15)	0.0136 (11)	0.0117 (14)	−0.0044 (12)
C20	0.0635 (14)	0.0615 (12)	0.0848 (16)	0.0066 (11)	0.0056 (14)	−0.0014 (12)
O2	0.0858 (12)	0.1315 (14)	0.1009 (12)	0.0447 (11)	0.0156 (11)	0.0126 (12)
C8	0.0585 (13)	0.0764 (13)	0.0662 (13)	0.0082 (12)	−0.0002 (11)	−0.0029 (11)
C16	0.0686 (15)	0.0780 (14)	0.0943 (17)	0.0114 (12)	−0.0031 (15)	−0.0093 (14)
C5	0.1023 (19)	0.0715 (14)	0.0649 (13)	−0.0134 (15)	0.0107 (14)	−0.0049 (11)
C1	0.0746 (16)	0.0562 (12)	0.0850 (16)	−0.0052 (12)	0.0086 (14)	0.0037 (12)
C6	0.0739 (16)	0.0567 (12)	0.0600 (12)	−0.0067 (12)	0.0075 (12)	0.0038 (10)
C19	0.0761 (16)	0.0802 (15)	0.0980 (18)	0.0085 (14)	0.0251 (16)	−0.0053 (14)
C17	0.104 (2)	0.0924 (17)	0.0795 (17)	0.0148 (16)	−0.0074 (17)	−0.0083 (14)
C3	0.116 (3)	0.0641 (16)	0.128 (2)	0.0091 (17)	0.046 (2)	0.0023 (16)
C2	0.0843 (18)	0.0730 (15)	0.125 (2)	0.0094 (15)	0.0115 (17)	0.0144 (16)
C18	0.104 (2)	0.0741 (15)	0.0870 (18)	0.0034 (16)	0.0185 (17)	−0.0029 (13)
C9	0.0863 (17)	0.0986 (16)	0.0734 (15)	0.0124 (15)	0.0108 (14)	0.0039 (13)
C4	0.133 (3)	0.0620 (15)	0.0916 (19)	−0.0111 (18)	0.037 (2)	−0.0087 (13)
C12	0.101 (2)	0.0944 (18)	0.1055 (19)	−0.0143 (16)	0.0050 (17)	−0.0323 (14)
C10	0.115 (2)	0.133 (2)	0.0689 (15)	0.028 (2)	−0.0044 (17)	−0.0073 (16)
C11	0.122 (2)	0.145 (3)	0.0947 (19)	−0.005 (2)	−0.0084 (19)	−0.0495 (19)

N2—C14	1.273 (3)	C5—H5	0.9300
N2—C13	1.467 (3)	C1—C2	1.390 (3)
N1—C7	1.285 (2)	C1—C6	1.402 (3)
N1—C8	1.467 (2)	C19—C18	1.373 (3)
C14—C15	1.453 (3)	C19—H19	0.9300
C14—H14	0.9300	C17—C18	1.359 (4)
O1—C1	1.366 (2)	C17—H17	0.9300
O1—H1	0.8200	C3—C4	1.358 (4)
C15—C16	1.389 (3)	C3—C2	1.372 (4)
C15—C20	1.411 (3)	C3—H3	0.9300
C7—C6	1.448 (3)	C2—H2A	0.9300
C7—H7	0.9300	C18—H18	0.9300
C13—C12	1.504 (3)	C9—C10	1.504 (4)
C13—C8	1.538 (3)	C9—H9A	0.9700
C13—H13	0.9800	C9—H9B	0.9700
C20—O2	1.355 (2)	C4—H4	0.9300
C20—C19	1.378 (3)	C12—C11	1.528 (4)
O2—H2	0.8200	C12—H12A	0.9700
C8—C9	1.523 (3)	C12—H12B	0.9700
C8—H8	0.9800	C10—C11	1.522 (4)
C16—C17	1.382 (3)	C10—H10A	0.9700
C16—H16	0.9300	C10—H10B	0.9700
C5—C4	1.381 (4)	C11—H11A	0.9700
C5—C6	1.400 (3)	C11—H11B	0.9700
C14—N2—C13	120.62 (18)	C18—C19—H19	119.8
C7—N1—C8	119.17 (18)	C20—C19—H19	119.8
N2—C14—C15	121.72 (19)	C18—C17—C16	119.4 (3)
N2—C14—H14	119.1	C18—C17—H17	120.3
C15—C14—H14	119.1	C16—C17—H17	120.3
C1—O1—H1	109.5	C4—C3—C2	121.6 (3)
C16—C15—C20	118.0 (2)	C4—C3—H3	119.2
C16—C15—C14	121.0 (2)	C2—C3—H3	119.2
C20—C15—C14	121.0 (2)	C3—C2—C1	119.5 (3)
N1—C7—C6	123.0 (2)	C3—C2—H2A	120.3
N1—C7—H7	118.5	C1—C2—H2A	120.3
C6—C7—H7	118.5	C17—C18—C19	121.1 (2)
N2—C13—C12	108.59 (19)	C17—C18—H18	119.5
N2—C13—C8	110.31 (16)	C19—C18—H18	119.5
C12—C13—C8	112.61 (19)	C10—C9—C8	112.5 (2)
N2—C13—H13	108.4	C10—C9—H9A	109.1
C12—C13—H13	108.4	C8—C9—H9A	109.1
C8—C13—H13	108.4	C10—C9—H9B	109.1
O2—C20—C19	119.4 (2)	C8—C9—H9B	109.1
O2—C20—C15	120.8 (2)	H9A—C9—H9B	107.8
C19—C20—C15	119.7 (2)	C3—C4—C5	119.6 (3)
C20—O2—H2	109.5	C3—C4—H4	120.2
N1—C8—C9	110.34 (17)	C5—C4—H4	120.2
N1—C8—C13	109.95 (16)	C13—C12—C11	111.4 (2)
C9—C8—C13	110.13 (17)	C13—C12—H12A	109.3
N1—C8—H8	108.8	C11—C12—H12A	109.3
C9—C8—H8	108.8	C13—C12—H12B	109.3
C13—C8—H8	108.8	C11—C12—H12B	109.3
C17—C16—C15	121.4 (2)	H12A—C12—H12B	108.0
C17—C16—H16	119.3	C9—C10—C11	110.9 (2)
C15—C16—H16	119.3	C9—C10—H10A	109.5
C4—C5—C6	121.0 (3)	C11—C10—H10A	109.5
C4—C5—H5	119.5	C9—C10—H10B	109.5
C6—C5—H5	119.5	C11—C10—H10B	109.5
O1—C1—C2	118.7 (2)	H10A—C10—H10B	108.1
O1—C1—C6	120.8 (2)	C10—C11—C12	110.6 (2)
C2—C1—C6	120.4 (2)	C10—C11—H11A	109.5
C5—C6—C1	117.9 (2)	C12—C11—H11A	109.5
C5—C6—C7	120.9 (2)	C10—C11—H11B	109.5
C1—C6—C7	121.2 (2)	C12—C11—H11B	109.5
C18—C19—C20	120.4 (2)	H11A—C11—H11B	108.1

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

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