2,2′-[(E,E)-cis-(Cyclo­hexane-1,4-di­yl)bis­(nitrilo­methanylyl­idene)]diphenol

Mohamed, S.K.; Akkurt, M.; Tahir, M.N.; Abdelhamid, A.A.

doi:10.1107/S1600536812023367

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1905

doi:10.1107/S1600536812023367

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2,2′-[(E,E)-cis-(Cyclohexane-1,4-diyl)bis(nitrilomethanylylidene)]diphenol

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Muhammad N. Tahir ^c and Antar A. Abdelhamid ^a

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 May 2012; accepted 22 May 2012; online 26 May 2012)

In the title compound, C₂₀H₂₂N₂O₂, the asymmetric unit contains two independent half-molecules, which are both completed by crystallographic inversion symmetry. The cyclohexane rings of both molecules adopt chair conformations; the N atoms are in equatorial orientations in one molecule and in axial orientations in the other. Both molecules feature two intramolecular 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_r = 322.40
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.140
S = 1.01
3428 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 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	1.85	2.579 (2)	148
O2—H2A⋯N2	0.82	1.86	2.593 (3)	148

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023367/hb6813sup1.cif

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

checkCIF report

Comment top

Schiff base compounds have been reported as excelent substrates in the development of coordination chemistry (e.g. Li & Zhang, 2004), In this study we report the synthesis and crystal structure of the title compound (I).

As shown in Fig. 1, there are two independent half molecules A (with C1) and B (with C11) in the asymmetric unit of the title compound. They are centrosymmetric and the centres of symmetry are lied on the centroids of their cyclohexane rings. The cyclohexane rings of them adopt chair conformations Molecular conformation of the title compound is stabilized by intramolecular O—H···N hydrogen bonds, generating an S(6) ring motif (Table 1, Fig. 2).

Related literature top

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

Experimental top

The title compound arose as a bi-product from heating a reaction mixture of 114 mg (1 mmol) cyclohexane-1,4-diamine, 112 mg (1 mmol) cyclohexane-1,3-dione and 122 mg (1 mmol) salicylaldehyde in 50 ml e thanol under reflux for 6 h. The reaction mixture was concentrated under vacuum then left to cool at ambient temperature. The obtained solid was collected by Buckner funnel, washed with water then ethanol, dried in desiccator and crystallized from ethanol (m.p. 451 K). Yellow prisms were grown from ethanol solution by slow evaporation over two days.

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewing along the b axis.

2,2'-[(E,E)-cis-(Cyclohexane-1,4- diyl)bis(nitrilomethanylylidene)]diphenol top

Crystal data top

C₂₀H₂₂N₂O₂	F(000) = 688
M_r = 322.40	D_x = 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

Data collection top

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

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0527P)² + 0.1881P] where P = (F_o² + 2F_c²)/3
3428 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₂	V = 1754.1 (2) Å³
M_r = 322.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.2979 (11) Å	µ = 0.08 mm⁻¹
b = 6.1103 (4) Å	T = 296 K
c = 18.2336 (12) Å	0.32 × 0.28 × 0.25 mm
β = 104.975 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3428 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1641 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.980	R_int = 0.041
12904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
3428 reflections	Δρ_min = −0.13 e Å⁻³
219 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O₂
M_r	322.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	16.2979 (11), 6.1103 (4), 18.2336 (12)
β (°)	104.975 (4)
V (Å³)	1754.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.28 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	12904, 3428, 1641
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.140, 1.01
No. of reflections	3428
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

This project was sponsored by the General Association of Scholarships in Egypt. The University of Sargodha is gratefully acknowledged for The X-ray difraction measurements and the data collection.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, m1017–m1019. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1905

doi:10.1107/S1600536812023367

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

2,2′-[(E,E)-cis-(Cyclo­hexane-1,4-di­yl)bis­­(nitrilo­methanylyl­­idene)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-[(E,E)-cis-(Cyclohexane-1,4-diyl)bis(nitrilomethanylylidene)]diphenol