2,2'-[(E,E)-cis-(Cyclo-hexane-1,4-di-yl)bis-(nitrilo-methanylyl-idene)]diphenol.

In the title compound, C(20)H(22)N(2)O(2), the asymmetric unit contains two independent half-mol-ecules, which are both completed by crystallographic inversion symmetry. The cyclo-hexane rings of both mol-ecules adopt chair conformations; the N atoms are in equatorial orientations in one mol-ecule and in axial orientations in the other. Both mol-ecules feature two intra-molecular O-H⋯N hydrogen bonds, which generate S(6) rings.

Related literature

For background to Schiff bases as ligands, see: Li & Zhang (2004 ▶).

Experimental

Crystal data

C20H22N2O2

M = 322.40

Monoclinic,

a = 16.2979 (11) Å

b = 6.1103 (4) Å

c = 18.2336 (12) Å

β = 104.975 (4)°

V = 1754.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.32 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.980

12904 measured reflections

3428 independent reflections

1641 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.140

S = 1.01

3428 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.13 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023367/hb6813sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023367/hb6813Isup2.hkl

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

C20H22N2O2	F(000) = 688
Mr = 322.40	Dx = 1.221 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 355 reflections
a = 16.2979 (11) Å	θ = 3.5–18°
b = 6.1103 (4) Å	µ = 0.08 mm−1
c = 18.2336 (12) Å	T = 296 K
β = 104.975 (4)°	Prism, light yellow
V = 1754.1 (2) Å3	0.32 × 0.28 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3428 independent reflections
Radiation source: fine-focus sealed tube	1641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 0.81 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −20→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.975, Tmax = 0.980	l = −22→22
12904 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1881P] where P = (Fo2 + 2Fc2)/3
3428 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.09064 (11)	−0.2099 (2)	0.21955 (9)	0.0798 (7)
N1	0.07675 (13)	0.0983 (3)	0.12044 (10)	0.0689 (8)
C1	0.13461 (14)	−0.0662 (4)	0.27110 (13)	0.0590 (9)
C2	0.16439 (15)	−0.1325 (4)	0.34525 (13)	0.0737 (10)
C3	0.20939 (17)	0.0070 (6)	0.39911 (15)	0.0845 (11)
C4	0.22627 (17)	0.2171 (6)	0.37967 (16)	0.0878 (14)
C5	0.19641 (15)	0.2847 (4)	0.30586 (15)	0.0732 (10)
C6	0.15061 (13)	0.1469 (4)	0.25003 (12)	0.0540 (8)
C7	0.11732 (14)	0.2225 (4)	0.17308 (13)	0.0629 (9)
C8	0.0412 (2)	0.1898 (4)	0.04433 (14)	0.0798 (12)
C9	0.07984 (17)	0.0747 (5)	−0.01193 (15)	0.0893 (13)
C10	−0.05416 (19)	0.1620 (5)	0.02264 (14)	0.0895 (13)
O2	0.24999 (12)	−0.0079 (3)	0.60105 (10)	0.0906 (8)
N2	0.15493 (13)	0.3363 (3)	0.59279 (11)	0.0689 (8)
C11	0.30811 (17)	0.0985 (4)	0.65534 (13)	0.0658 (10)
C12	0.3858 (2)	−0.0030 (4)	0.68695 (16)	0.0789 (11)
C13	0.44577 (18)	0.1016 (5)	0.74179 (17)	0.0835 (12)
C14	0.43165 (18)	0.3068 (5)	0.76653 (15)	0.0827 (12)
C15	0.35547 (17)	0.4075 (4)	0.73567 (14)	0.0726 (10)
C16	0.29237 (15)	0.3078 (4)	0.67939 (13)	0.0594 (9)
C17	0.21310 (16)	0.4199 (4)	0.64521 (13)	0.0639 (9)
C18	0.07848 (17)	0.4641 (4)	0.56020 (12)	0.0707 (10)
C19	0.08057 (16)	0.5442 (5)	0.48189 (14)	0.0877 (11)
C20	0.00025 (17)	0.3308 (5)	0.55562 (15)	0.0893 (11)
H1	0.07470	−0.14950	0.17810	0.0960*
H2	0.15370	−0.27440	0.35880	0.0880*
H3	0.22880	−0.03980	0.44920	0.1020*
H4	0.25760	0.31200	0.41620	0.1050*
H5	0.20730	0.42720	0.29300	0.0880*
H7	0.12590	0.36770	0.16170	0.0760*
H8	0.05480	0.34610	0.04490	0.0960*
H9A	0.06250	0.14910	−0.06050	0.1070*
H9B	0.14120	0.08380	0.00550	0.1070*
H10A	−0.07710	0.22480	0.06200	0.1070*
H10B	−0.07820	0.24110	−0.02410	0.1070*
H2A	0.20730	0.06790	0.58720	0.1090*
H12	0.39670	−0.14170	0.67070	0.0950*
H13	0.49730	0.03250	0.76290	0.1000*
H14	0.47330	0.37660	0.80380	0.0990*
H15	0.34570	0.54600	0.75280	0.0870*
H17	0.20470	0.55910	0.66260	0.0770*
H18	0.07770	0.59130	0.59280	0.0850*
H19A	0.08650	0.42010	0.45050	0.1050*
H19B	0.12940	0.63890	0.48620	0.1050*
H20A	−0.00150	0.28800	0.60640	0.1070*
H20B	0.00280	0.19850	0.52690	0.1070*

	U11	U22	U33	U12	U13	U23
O1	0.1064 (14)	0.0639 (10)	0.0648 (11)	−0.0200 (10)	0.0146 (10)	0.0018 (8)
N1	0.0927 (15)	0.0592 (12)	0.0533 (12)	−0.0029 (11)	0.0160 (10)	0.0030 (10)
C1	0.0618 (15)	0.0655 (16)	0.0526 (14)	−0.0007 (13)	0.0202 (11)	−0.0056 (12)
C2	0.0842 (19)	0.0826 (18)	0.0583 (16)	0.0068 (15)	0.0257 (13)	0.0046 (14)
C3	0.084 (2)	0.114 (2)	0.0565 (17)	0.0167 (18)	0.0201 (14)	−0.0041 (17)
C4	0.0716 (19)	0.114 (3)	0.073 (2)	−0.0034 (17)	0.0099 (15)	−0.0310 (18)
C5	0.0669 (17)	0.0738 (17)	0.0834 (19)	−0.0097 (13)	0.0274 (14)	−0.0203 (15)
C6	0.0537 (14)	0.0567 (14)	0.0558 (14)	−0.0014 (11)	0.0217 (11)	−0.0057 (12)
C7	0.0736 (17)	0.0543 (14)	0.0672 (16)	−0.0008 (12)	0.0296 (13)	0.0013 (13)
C8	0.120 (3)	0.0562 (15)	0.0589 (16)	0.0001 (16)	0.0152 (16)	0.0100 (13)
C9	0.083 (2)	0.120 (3)	0.0661 (18)	−0.0034 (18)	0.0212 (14)	0.0239 (17)
C10	0.107 (3)	0.100 (2)	0.0625 (17)	0.0366 (19)	0.0238 (16)	−0.0014 (15)
O2	0.1192 (16)	0.0754 (12)	0.0774 (13)	0.0202 (11)	0.0259 (11)	−0.0102 (10)
N2	0.0781 (15)	0.0755 (14)	0.0541 (12)	0.0147 (12)	0.0189 (10)	0.0012 (11)
C11	0.085 (2)	0.0656 (17)	0.0548 (15)	0.0085 (15)	0.0327 (14)	0.0045 (13)
C12	0.101 (2)	0.0716 (18)	0.0787 (19)	0.0263 (18)	0.0497 (17)	0.0179 (15)
C13	0.073 (2)	0.104 (2)	0.084 (2)	0.0205 (18)	0.0391 (17)	0.0301 (18)
C14	0.067 (2)	0.097 (2)	0.088 (2)	−0.0028 (17)	0.0271 (15)	0.0135 (17)
C15	0.0768 (19)	0.0668 (16)	0.0809 (18)	−0.0025 (15)	0.0324 (15)	0.0048 (14)
C16	0.0693 (17)	0.0588 (15)	0.0594 (15)	0.0058 (13)	0.0335 (13)	0.0077 (12)
C17	0.0772 (18)	0.0605 (15)	0.0622 (16)	0.0092 (14)	0.0328 (13)	0.0061 (13)
C18	0.0829 (19)	0.0775 (17)	0.0530 (15)	0.0188 (16)	0.0202 (12)	0.0007 (13)
C19	0.0816 (19)	0.109 (2)	0.0774 (19)	0.0142 (17)	0.0296 (14)	0.0299 (16)
C20	0.089 (2)	0.104 (2)	0.0797 (19)	0.0131 (19)	0.0304 (15)	0.0309 (16)

O1—C1	1.349 (3)	C9—H9A	0.9700
O1—H1	0.8200	C9—H9B	0.9700
O2—C11	1.347 (3)	C10—H10B	0.9700
O2—H2A	0.8200	C10—H10A	0.9700
N1—C7	1.267 (3)	C11—C16	1.397 (3)
N1—C8	1.469 (3)	C11—C12	1.394 (4)
N2—C18	1.460 (3)	C12—C13	1.363 (4)
N2—C17	1.267 (3)	C13—C14	1.372 (4)
C1—C6	1.401 (3)	C14—C15	1.370 (4)
C1—C2	1.374 (3)	C15—C16	1.392 (4)
C2—C3	1.363 (4)	C16—C17	1.453 (4)
C3—C4	1.378 (5)	C18—C20	1.497 (4)
C4—C5	1.371 (4)	C18—C19	1.518 (3)
C5—C6	1.382 (3)	C19—C20ii	1.523 (4)
C6—C7	1.443 (3)	C12—H12	0.9300
C8—C10	1.511 (5)	C13—H13	0.9300
C8—C9	1.509 (4)	C14—H14	0.9300
C9—C10i	1.504 (4)	C15—H15	0.9300
C2—H2	0.9300	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9800
C4—H4	0.9300	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C7—H7	0.9300	C20—H20A	0.9700
C8—H8	0.9800	C20—H20B	0.9700
C1—O1—H1	109.00	H10A—C10—H10B	108.00
C11—O2—H2A	109.00	C8—C10—H10A	109.00
C7—N1—C8	119.3 (2)	O2—C11—C12	118.7 (2)
C17—N2—C18	119.0 (2)	C12—C11—C16	119.9 (2)
O1—C1—C2	118.9 (2)	O2—C11—C16	121.4 (2)
C2—C1—C6	120.0 (2)	C11—C12—C13	119.8 (2)
O1—C1—C6	121.1 (2)	C12—C13—C14	121.4 (3)
C1—C2—C3	120.8 (2)	C13—C14—C15	119.1 (3)
C2—C3—C4	120.2 (3)	C14—C15—C16	121.7 (2)
C3—C4—C5	119.3 (3)	C11—C16—C15	118.1 (2)
C4—C5—C6	121.8 (3)	C11—C16—C17	120.8 (2)
C1—C6—C5	117.9 (2)	C15—C16—C17	121.1 (2)
C1—C6—C7	120.9 (2)	N2—C17—C16	122.9 (2)
C5—C6—C7	121.1 (2)	N2—C18—C19	109.3 (2)
N1—C7—C6	122.4 (2)	N2—C18—C20	110.9 (2)
N1—C8—C10	109.4 (2)	C19—C18—C20	110.4 (2)
C9—C8—C10	110.6 (2)	C18—C19—C20ii	110.9 (2)
N1—C8—C9	109.4 (2)	C18—C20—C19ii	112.2 (2)
C8—C9—C10i	112.7 (2)	C11—C12—H12	120.00
C8—C10—C9i	112.0 (2)	C13—C12—H12	120.00
C1—C2—H2	120.00	C12—C13—H13	119.00
C3—C2—H2	120.00	C14—C13—H13	119.00
C4—C3—H3	120.00	C13—C14—H14	120.00
C2—C3—H3	120.00	C15—C14—H14	120.00
C3—C4—H4	120.00	C14—C15—H15	119.00
C5—C4—H4	120.00	C16—C15—H15	119.00
C6—C5—H5	119.00	N2—C17—H17	119.00
C4—C5—H5	119.00	C16—C17—H17	119.00
C6—C7—H7	119.00	N2—C18—H18	109.00
N1—C7—H7	119.00	C19—C18—H18	109.00
C9—C8—H8	109.00	C20—C18—H18	109.00
C10—C8—H8	109.00	C18—C19—H19A	109.00
N1—C8—H8	109.00	C18—C19—H19B	109.00
C8—C9—H9B	109.00	H19A—C19—H19B	108.00
C8—C9—H9A	109.00	C20ii—C19—H19A	109.00
C10i—C9—H9B	109.00	C20ii—C19—H19B	109.00
H9A—C9—H9B	108.00	C18—C20—H20A	109.00
C10i—C9—H9A	109.00	C18—C20—H20B	109.00
C8—C10—H10B	109.00	H20A—C20—H20B	108.00
C9i—C10—H10A	109.00	C19ii—C20—H20A	109.00
C9i—C10—H10B	109.00	C19ii—C20—H20B	109.00
C8—N1—C7—C6	177.0 (2)	N1—C8—C10—C9i	−67.2 (3)
C7—N1—C8—C9	119.4 (3)	C9—C8—C10—C9i	53.4 (3)
C7—N1—C8—C10	−119.3 (3)	C8—C9—C10i—C8i	54.6 (3)
C18—N2—C17—C16	−178.1 (2)	O2—C11—C12—C13	179.8 (3)
C17—N2—C18—C19	105.8 (3)	C16—C11—C12—C13	0.7 (4)
C17—N2—C18—C20	−132.2 (2)	O2—C11—C16—C15	−179.9 (2)
O1—C1—C2—C3	179.7 (2)	O2—C11—C16—C17	−1.4 (4)
C6—C1—C2—C3	0.2 (4)	C12—C11—C16—C15	−0.9 (4)
O1—C1—C6—C5	−179.7 (2)	C12—C11—C16—C17	177.7 (2)
C2—C1—C6—C7	−177.7 (2)	C11—C12—C13—C14	−0.4 (5)
O1—C1—C6—C7	2.8 (3)	C12—C13—C14—C15	0.4 (4)
C2—C1—C6—C5	−0.2 (3)	C13—C14—C15—C16	−0.6 (4)
C1—C2—C3—C4	−0.5 (4)	C14—C15—C16—C11	0.8 (4)
C2—C3—C4—C5	0.8 (4)	C14—C15—C16—C17	−177.7 (2)
C3—C4—C5—C6	−0.8 (4)	C11—C16—C17—N2	0.0 (4)
C4—C5—C6—C1	0.5 (4)	C15—C16—C17—N2	178.5 (2)
C4—C5—C6—C7	178.0 (2)	N2—C18—C19—C20ii	177.3 (2)
C1—C6—C7—N1	−4.2 (4)	C20—C18—C19—C20ii	55.0 (3)
C5—C6—C7—N1	178.4 (2)	N2—C18—C20—C19ii	−177.1 (2)
C10—C8—C9—C10i	−53.8 (3)	C19—C18—C20—C19ii	−55.7 (3)
N1—C8—C9—C10i	66.8 (3)	C18—C19—C20ii—C18ii	−56.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.579 (2)	148
O2—H2A···N2	0.82	1.86	2.593 (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	1.85	2.579 (2)	148
O2—H2A⋯N2	0.82	1.86	2.593 (3)	148