6,6′-Dimeth­oxy-2,2′-[(cyclo­hexane-1,2-di­yl)bis­(nitrilo­methyl­idyne)]diphenol

Zhang, Q.; Yan, P.-F.; Li, G.-M.; Chen, P.

doi:10.1107/S1600536810033465

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2450

https://doi.org/10.1107/S1600536810033465

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6,6′-Dimethoxy-2,2′-[(cyclohexane-1,2-diyl)bis(nitrilomethylidyne)]diphenol

Qian Zhang,^a Peng-Fei Yan,^a Guang-Ming Li ^a and Peng Chen ^a ^*

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: jehugu@yahoo.com.cn

(Received 22 July 2010; accepted 19 August 2010; online 28 August 2010)

The molecule of the title compound, C₂₂H₂₆N₂O₄, has two azomethine linkages, both of which are in an E configuration. The cyclohexyl ring adopts a chair conformation. The dihedral angle between the benzene rings is 66.57 (9)°. The molecular structure is stabilized by two intramolecular O—H⋯N hydrogen bonds.

Related literature

For related structures, see: Aslantaş et al. (2007 ); Tozzo et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₆N₂O₄
M_r = 382.45
Monoclinic, P 2₁ /c
a = 15.014 (3) Å
b = 12.029 (2) Å
c = 12.099 (2) Å
β = 107.54 (3)°
V = 2083.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
19987 measured reflections
4748 independent reflections
2352 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.164
S = 1.03
4748 reflections
259 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.88 (2)	1.77 (2)	2.572 (3)	150 (3)
O4—H4⋯N2	0.86 (3)	1.80 (3)	2.587 (3)	152 (3)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810033465/ng5006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033465/ng5006Isup2.hkl

checkCIF report

Comment top

We present the crystal structure of the title compound, as shown in Fig. 1. X-ray analysis suggests that the imino group is in the trans configuration and the two aromatic rings are lying on in front of the other. Bond lengths and angles within the aromatic rings are consistent with reported examples. Short H-bonds exists between the OH groups and the imino groups in ortho position.

Related literature top

For related structures, see: Aslantaş et al. (2007); Tozzo et al. (2008).

Experimental top

The title compound was prepared by a known method. o-Vanillin (2 mmol, 0.304 g) in acetontrile (20 ml) and trans-1,2-cyclohexanediamine (1 mmol, 0.114 g) in methanol (20 ml) were mixed and refluxed for about 4 h at 358 K. The reaction mixture was cooled and filtered; Compound was obtained by crystallization from a mixture methanol/acetonitrile solution after a few days. Analysis: calculated for C₂₂H₂₆N₂O₄: C 69.09, H 6.85, N 7.32, O 16.73%; found: C 69.21, H.7.01, N 23.78%.

Structure description top

For related structures, see: Aslantaş et al. (2007); Tozzo et al. (2008).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.

6,6'-Dimethoxy-2,2'-[(cyclohexane-1,2-diyl)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₂H₂₆N₂O₄	F(000) = 816
M_r = 382.45	D_x = 1.219 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4748 reflections
a = 15.014 (3) Å	θ = 3.1–27.5°
b = 12.029 (2) Å	µ = 0.08 mm⁻¹
c = 12.099 (2) Å	T = 293 K
β = 107.54 (3)°	Block, yellow
V = 2083.5 (6) Å³	0.22 × 0.20 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2352 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
Detector resolution: 10.000 pixels mm^-1	h = −19→19
ω scans	k = −15→15
19987 measured reflections	l = −15→14
4748 independent 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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0509P)² + 0.6508P] where P = (F_o² + 2F_c²)/3
4748 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₂H₂₆N₂O₄	V = 2083.5 (6) Å³
M_r = 382.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.014 (3) Å	µ = 0.08 mm⁻¹
b = 12.029 (2) Å	T = 293 K
c = 12.099 (2) Å	0.22 × 0.20 × 0.15 mm
β = 107.54 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2352 reflections with I > 2σ(I)
19987 measured reflections	R_int = 0.062
4748 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	1 restraint
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.13 e Å⁻³
4748 reflections	Δρ_min = −0.18 e Å⁻³
259 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

	x	y	z	U_iso*/U_eq
C1	0.0604 (3)	0.6458 (3)	0.0711 (3)	0.1152 (12)
H1A	0.0594	0.6532	−0.0083	0.173*
H1B	0.1008	0.7015	0.1171	0.173*
H1C	−0.0016	0.6553	0.0765	0.173*
C2	0.0895 (3)	0.5459 (3)	0.4138 (4)	0.1002 (11)
H2A	0.0743	0.5934	0.4661	0.120*
C3	0.6339 (2)	0.4074 (3)	0.4551 (3)	0.0913 (10)
H3A	0.6771	0.4377	0.4223	0.110*
C4	0.2019 (2)	−0.1264 (2)	0.3541 (3)	0.0877 (9)
H4A	0.2139	−0.1370	0.4368	0.105*
H4B	0.1573	−0.1825	0.3140	0.105*
C5	0.1206 (2)	0.4412 (3)	0.4475 (3)	0.0897 (9)
H5A	0.1276	0.4182	0.5231	0.108*
C6	0.2916 (2)	−0.1400 (2)	0.3237 (3)	0.0832 (9)
H6A	0.2788	−0.1342	0.2404	0.100*
H6B	0.3175	−0.2132	0.3475	0.100*
C7	0.6257 (2)	0.5092 (3)	0.7826 (3)	0.1011 (11)
H7A	0.6137	0.5225	0.8550	0.152*
H7B	0.6185	0.5774	0.7395	0.152*
H7C	0.6883	0.4821	0.7971	0.152*
C8	0.5739 (2)	0.3277 (3)	0.3967 (2)	0.0801 (9)
H8A	0.5761	0.3042	0.3243	0.096*
C9	0.0802 (2)	0.5821 (2)	0.3029 (3)	0.0869 (9)
H9A	0.0599	0.6542	0.2813	0.104*
C10	0.36190 (19)	−0.0523 (2)	0.3828 (2)	0.0712 (8)
H10A	0.4176	−0.0605	0.3587	0.085*
H10B	0.3796	−0.0634	0.4660	0.085*
C11	0.16120 (19)	−0.0121 (2)	0.3201 (3)	0.0805 (9)
H11A	0.1046	−0.0040	0.3421	0.097*
H11B	0.1449	−0.0038	0.2366	0.097*
C12	0.10074 (19)	0.5126 (2)	0.2240 (3)	0.0721 (8)
C13	0.14201 (18)	0.3684 (2)	0.3698 (2)	0.0645 (7)
C14	0.6317 (2)	0.4439 (2)	0.5620 (2)	0.0732 (8)
H14A	0.6731	0.4987	0.6009	0.088*
C15	0.17636 (18)	0.2574 (2)	0.4061 (2)	0.0658 (7)
H15A	0.1869	0.2370	0.4831	0.079*
C16	0.23034 (17)	0.0781 (2)	0.3785 (2)	0.0605 (7)
H16A	0.2407	0.0746	0.4624	0.073*
C17	0.13111 (18)	0.4042 (2)	0.2567 (3)	0.0677 (7)
C18	0.56880 (19)	0.3998 (2)	0.6112 (2)	0.0605 (7)
C19	0.50689 (17)	0.3178 (2)	0.5532 (2)	0.0546 (6)
C20	0.32359 (16)	0.0644 (2)	0.3545 (2)	0.0565 (6)
H20A	0.3149	0.0794	0.2723	0.068*
C21	0.50889 (17)	0.2810 (2)	0.44483 (19)	0.0558 (6)
C22	0.44426 (17)	0.1969 (2)	0.3816 (2)	0.0574 (6)
H22A	0.4441	0.1787	0.3068	0.069*
N1	0.19248 (14)	0.18712 (18)	0.33625 (18)	0.0628 (6)
N2	0.38790 (14)	0.14722 (17)	0.42452 (16)	0.0568 (5)
O1	0.56134 (14)	0.42882 (16)	0.71764 (15)	0.0826 (6)
O2	0.09388 (17)	0.53935 (17)	0.1121 (2)	0.1010 (7)
O3	0.15024 (16)	0.33730 (17)	0.17764 (17)	0.0920 (7)
H3	0.166 (3)	0.2728 (19)	0.211 (3)	0.138*
O4	0.44555 (14)	0.27515 (16)	0.60379 (15)	0.0754 (6)
H4	0.414 (2)	0.225 (3)	0.557 (3)	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.121 (3)	0.082 (2)	0.148 (3)	0.027 (2)	0.048 (3)	0.034 (2)
C2	0.113 (3)	0.078 (2)	0.125 (3)	−0.003 (2)	0.058 (2)	−0.029 (2)
C3	0.093 (2)	0.111 (3)	0.081 (2)	−0.041 (2)	0.0441 (18)	−0.012 (2)
C4	0.082 (2)	0.0693 (19)	0.112 (2)	−0.0142 (16)	0.0286 (19)	0.0015 (18)
C5	0.105 (3)	0.081 (2)	0.095 (2)	−0.0020 (19)	0.049 (2)	−0.0140 (19)
C6	0.083 (2)	0.0656 (18)	0.098 (2)	0.0009 (16)	0.0235 (18)	−0.0063 (17)
C7	0.116 (3)	0.106 (2)	0.073 (2)	−0.028 (2)	0.0178 (19)	−0.0256 (19)
C8	0.086 (2)	0.099 (2)	0.0646 (17)	−0.0261 (18)	0.0367 (16)	−0.0097 (16)
C9	0.075 (2)	0.0583 (18)	0.130 (3)	−0.0048 (15)	0.036 (2)	−0.011 (2)
C10	0.0629 (18)	0.0709 (18)	0.0779 (18)	0.0088 (15)	0.0182 (14)	0.0011 (15)
C11	0.0510 (17)	0.082 (2)	0.105 (2)	−0.0047 (15)	0.0185 (16)	0.0027 (18)
C12	0.0568 (18)	0.0676 (19)	0.089 (2)	0.0003 (14)	0.0181 (15)	−0.0017 (17)
C13	0.0553 (16)	0.0637 (17)	0.0768 (18)	−0.0028 (13)	0.0231 (14)	−0.0080 (15)
C14	0.071 (2)	0.0743 (18)	0.0709 (18)	−0.0194 (15)	0.0154 (15)	−0.0041 (15)
C15	0.0591 (17)	0.0781 (19)	0.0619 (15)	−0.0067 (14)	0.0207 (13)	−0.0010 (15)
C16	0.0526 (16)	0.0638 (16)	0.0643 (15)	0.0046 (13)	0.0163 (12)	0.0075 (13)
C17	0.0513 (16)	0.0673 (18)	0.0813 (19)	0.0062 (14)	0.0150 (14)	−0.0084 (16)
C18	0.0653 (17)	0.0625 (16)	0.0514 (14)	0.0017 (14)	0.0142 (13)	0.0037 (13)
C19	0.0539 (15)	0.0601 (15)	0.0508 (14)	0.0007 (13)	0.0175 (12)	0.0066 (12)
C20	0.0523 (15)	0.0650 (16)	0.0519 (13)	−0.0002 (13)	0.0151 (12)	0.0026 (13)
C21	0.0546 (16)	0.0651 (16)	0.0475 (13)	−0.0021 (13)	0.0151 (12)	0.0028 (12)
C22	0.0566 (16)	0.0722 (17)	0.0446 (13)	0.0030 (13)	0.0170 (12)	0.0015 (13)
N1	0.0553 (13)	0.0680 (14)	0.0620 (13)	0.0058 (11)	0.0129 (11)	−0.0021 (12)
N2	0.0513 (13)	0.0666 (13)	0.0527 (11)	−0.0026 (10)	0.0157 (10)	0.0019 (10)
O1	0.0954 (15)	0.0916 (14)	0.0620 (11)	−0.0214 (12)	0.0258 (10)	−0.0159 (11)
O2	0.1142 (18)	0.0841 (15)	0.1000 (17)	0.0303 (13)	0.0250 (14)	0.0171 (13)
O3	0.1182 (18)	0.0836 (14)	0.0708 (13)	0.0356 (13)	0.0233 (12)	0.0012 (11)
O4	0.0820 (14)	0.0921 (15)	0.0601 (11)	−0.0245 (11)	0.0335 (10)	−0.0087 (10)

Geometric parameters (Å, º) top

C1—O2	1.410 (3)	C10—H10A	0.9700
C1—H1A	0.9600	C10—H10B	0.9700
C1—H1B	0.9600	C11—C16	1.521 (3)
C1—H1C	0.9600	C11—H11A	0.9700
C2—C5	1.363 (4)	C11—H11B	0.9700
C2—C9	1.378 (4)	C12—O2	1.365 (3)
C2—H2A	0.9300	C12—C17	1.399 (4)
C3—C8	1.358 (4)	C13—C17	1.396 (4)
C3—C14	1.377 (4)	C13—C15	1.452 (4)
C3—H3A	0.9300	C14—C18	1.367 (3)
C4—C6	1.509 (4)	C14—H14A	0.9300
C4—C11	1.510 (4)	C15—N1	1.269 (3)
C4—H4A	0.9700	C15—H15A	0.9300
C4—H4B	0.9700	C16—N1	1.459 (3)
C5—C13	1.392 (4)	C16—C20	1.522 (3)
C5—H5A	0.9300	C16—H16A	0.9800
C6—C10	1.511 (4)	C17—O3	1.346 (3)
C6—H6A	0.9700	C18—O1	1.371 (3)
C6—H6B	0.9700	C18—C19	1.392 (3)
C7—O1	1.425 (3)	C19—O4	1.351 (3)
C7—H7A	0.9600	C19—C21	1.393 (3)
C7—H7B	0.9600	C20—N2	1.466 (3)
C7—H7C	0.9600	C20—H20A	0.9800
C8—C21	1.397 (3)	C21—C22	1.450 (3)
C8—H8A	0.9300	C22—N2	1.268 (3)
C9—C12	1.371 (4)	C22—H22A	0.9300
C9—H9A	0.9300	O3—H3	0.876 (18)
C10—C20	1.516 (3)	O4—H4	0.86 (3)

O2—C1—H1A	109.5	C4—C11—H11B	109.4
O2—C1—H1B	109.5	C16—C11—H11B	109.4
H1A—C1—H1B	109.5	H11A—C11—H11B	108.0
O2—C1—H1C	109.5	O2—C12—C9	125.5 (3)
H1A—C1—H1C	109.5	O2—C12—C17	114.9 (3)
H1B—C1—H1C	109.5	C9—C12—C17	119.6 (3)
C5—C2—C9	120.6 (3)	C5—C13—C17	119.1 (3)
C5—C2—H2A	119.7	C5—C13—C15	120.5 (3)
C9—C2—H2A	119.7	C17—C13—C15	120.4 (2)
C8—C3—C14	121.0 (3)	C18—C14—C3	120.0 (3)
C8—C3—H3A	119.5	C18—C14—H14A	120.0
C14—C3—H3A	119.5	C3—C14—H14A	120.0
C6—C4—C11	110.5 (2)	N1—C15—C13	122.2 (3)
C6—C4—H4A	109.6	N1—C15—H15A	118.9
C11—C4—H4A	109.6	C13—C15—H15A	118.9
C6—C4—H4B	109.6	N1—C16—C11	109.8 (2)
C11—C4—H4B	109.6	N1—C16—C20	108.3 (2)
H4A—C4—H4B	108.1	C11—C16—C20	111.9 (2)
C2—C5—C13	120.5 (3)	N1—C16—H16A	108.9
C2—C5—H5A	119.8	C11—C16—H16A	108.9
C13—C5—H5A	119.8	C20—C16—H16A	108.9
C4—C6—C10	110.9 (2)	O3—C17—C13	121.7 (2)
C4—C6—H6A	109.5	O3—C17—C12	118.5 (3)
C10—C6—H6A	109.5	C13—C17—C12	119.7 (3)
C4—C6—H6B	109.5	C14—C18—O1	125.0 (2)
C10—C6—H6B	109.5	C14—C18—C19	120.0 (2)
H6A—C6—H6B	108.0	O1—C18—C19	115.0 (2)
O1—C7—H7A	109.5	O4—C19—C18	118.9 (2)
O1—C7—H7B	109.5	O4—C19—C21	121.1 (2)
H7A—C7—H7B	109.5	C18—C19—C21	120.0 (2)
O1—C7—H7C	109.5	N2—C20—C10	111.1 (2)
H7A—C7—H7C	109.5	N2—C20—C16	107.46 (19)
H7B—C7—H7C	109.5	C10—C20—C16	111.4 (2)
C3—C8—C21	120.3 (3)	N2—C20—H20A	108.9
C3—C8—H8A	119.9	C10—C20—H20A	108.9
C21—C8—H8A	119.9	C16—C20—H20A	108.9
C12—C9—C2	120.5 (3)	C19—C21—C8	118.7 (2)
C12—C9—H9A	119.8	C19—C21—C22	121.2 (2)
C2—C9—H9A	119.8	C8—C21—C22	120.1 (2)
C6—C10—C20	112.1 (2)	N2—C22—C21	122.4 (2)
C6—C10—H10A	109.2	N2—C22—H22A	118.8
C20—C10—H10A	109.2	C21—C22—H22A	118.8
C6—C10—H10B	109.2	C15—N1—C16	119.8 (2)
C20—C10—H10B	109.2	C22—N2—C20	119.2 (2)
H10A—C10—H10B	107.9	C18—O1—C7	117.2 (2)
C4—C11—C16	111.1 (2)	C12—O2—C1	118.4 (3)
C4—C11—H11A	109.4	C17—O3—H3	107 (2)
C16—C11—H11A	109.4	C19—O4—H4	106 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.88 (2)	1.77 (2)	2.572 (3)	150 (3)
O4—H4···N2	0.86 (3)	1.80 (3)	2.587 (3)	152 (3)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆N₂O₄
M_r	382.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.014 (3), 12.029 (2), 12.099 (2)
β (°)	107.54 (3)
V (Å³)	2083.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19987, 4748, 2352
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.164, 1.03
No. of reflections	4748
No. of parameters	259
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.876 (18)	1.77 (2)	2.572 (3)	150 (3)
O4—H4···N2	0.86 (3)	1.80 (3)	2.587 (3)	152 (3)

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (Nos. 20872030 and 20972043), Heilongjiang Province (Nos. 2009RFXXG201, GC09A402 and 2010 t d03) and Heilongjiang University.

References

Aslantaş, M., Tümer, M., Şahin, E. & Tümer, F. (2007). Acta Cryst. E63, o644–o645. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tozzo, E., Romera, S., Santos, M. P., Muraro, M., Santos, R. H. De A., Liao, L. M., Vizotto, L. & Dockal, E. R. (2008). J. Mol. Struct. 876, 110–120. Google Scholar

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Volume 66| Part 9| September 2010| Page o2450

https://doi.org/10.1107/S1600536810033465

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

6,6′-Dimeth­­oxy-2,2′-[(cyclo­hexane-1,2-di­yl)bis­­(nitrilo­methyl­­idyne)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Dimethoxy-2,2′-[(cyclohexane-1,2-diyl)bis(nitrilomethylidyne)]diphenol