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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2450.
Published online 2010 August 28. doi:  10.1107/S1600536810033465
PMCID: PMC3008137

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

Abstract

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 [triangle]); Tozzo et al. (2008 [triangle]).

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Object name is e-66-o2450-scheme1.jpg

Experimental

Crystal data

  • C22H26N2O4
  • M r = 382.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2450-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.164
  • S = 1.03
  • 4748 reflections
  • 259 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033465/ng5006Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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%.

Refinement

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97Å (methylene C), and with Uiso(H) = 1.2Ueq(C) or C—H = 0.96 Å (methly C) and with Uiso(H) = 1.5Ueq(C). The H atoms attached to the O atoms were found from the Fourier difference map and the O–H bonds are refined in the normal range with Uiso(H) = 1.5Ueq(O).

Figures

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

Crystal data

C22H26N2O4F(000) = 816
Mr = 382.45Dx = 1.219 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4748 reflections
a = 15.014 (3) Åθ = 3.1–27.5°
b = 12.029 (2) ŵ = 0.08 mm1
c = 12.099 (2) ÅT = 293 K
β = 107.54 (3)°Block, yellow
V = 2083.5 (6) Å30.22 × 0.20 × 0.15 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer2352 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
graphiteθmax = 27.5°, θmin = 3.1°
Detector resolution: 10.000 pixels mm-1h = −19→19
ω scansk = −15→15
19987 measured reflectionsl = −15→14
4748 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6508P] where P = (Fo2 + 2Fc2)/3
4748 reflections(Δ/σ)max = 0.001
259 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = −0.18 e Å3

Special details

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)

xyzUiso*/Ueq
C10.0604 (3)0.6458 (3)0.0711 (3)0.1152 (12)
H1A0.05940.6532−0.00830.173*
H1B0.10080.70150.11710.173*
H1C−0.00160.65530.07650.173*
C20.0895 (3)0.5459 (3)0.4138 (4)0.1002 (11)
H2A0.07430.59340.46610.120*
C30.6339 (2)0.4074 (3)0.4551 (3)0.0913 (10)
H3A0.67710.43770.42230.110*
C40.2019 (2)−0.1264 (2)0.3541 (3)0.0877 (9)
H4A0.2139−0.13700.43680.105*
H4B0.1573−0.18250.31400.105*
C50.1206 (2)0.4412 (3)0.4475 (3)0.0897 (9)
H5A0.12760.41820.52310.108*
C60.2916 (2)−0.1400 (2)0.3237 (3)0.0832 (9)
H6A0.2788−0.13420.24040.100*
H6B0.3175−0.21320.34750.100*
C70.6257 (2)0.5092 (3)0.7826 (3)0.1011 (11)
H7A0.61370.52250.85500.152*
H7B0.61850.57740.73950.152*
H7C0.68830.48210.79710.152*
C80.5739 (2)0.3277 (3)0.3967 (2)0.0801 (9)
H8A0.57610.30420.32430.096*
C90.0802 (2)0.5821 (2)0.3029 (3)0.0869 (9)
H9A0.05990.65420.28130.104*
C100.36190 (19)−0.0523 (2)0.3828 (2)0.0712 (8)
H10A0.4176−0.06050.35870.085*
H10B0.3796−0.06340.46600.085*
C110.16120 (19)−0.0121 (2)0.3201 (3)0.0805 (9)
H11A0.1046−0.00400.34210.097*
H11B0.1449−0.00380.23660.097*
C120.10074 (19)0.5126 (2)0.2240 (3)0.0721 (8)
C130.14201 (18)0.3684 (2)0.3698 (2)0.0645 (7)
C140.6317 (2)0.4439 (2)0.5620 (2)0.0732 (8)
H14A0.67310.49870.60090.088*
C150.17636 (18)0.2574 (2)0.4061 (2)0.0658 (7)
H15A0.18690.23700.48310.079*
C160.23034 (17)0.0781 (2)0.3785 (2)0.0605 (7)
H16A0.24070.07460.46240.073*
C170.13111 (18)0.4042 (2)0.2567 (3)0.0677 (7)
C180.56880 (19)0.3998 (2)0.6112 (2)0.0605 (7)
C190.50689 (17)0.3178 (2)0.5532 (2)0.0546 (6)
C200.32359 (16)0.0644 (2)0.3545 (2)0.0565 (6)
H20A0.31490.07940.27230.068*
C210.50889 (17)0.2810 (2)0.44483 (19)0.0558 (6)
C220.44426 (17)0.1969 (2)0.3816 (2)0.0574 (6)
H22A0.44410.17870.30680.069*
N10.19248 (14)0.18712 (18)0.33625 (18)0.0628 (6)
N20.38790 (14)0.14722 (17)0.42452 (16)0.0568 (5)
O10.56134 (14)0.42882 (16)0.71764 (15)0.0826 (6)
O20.09388 (17)0.53935 (17)0.1121 (2)0.1010 (7)
O30.15024 (16)0.33730 (17)0.17764 (17)0.0920 (7)
H30.166 (3)0.2728 (19)0.211 (3)0.138*
O40.44555 (14)0.27515 (16)0.60379 (15)0.0754 (6)
H40.414 (2)0.225 (3)0.557 (3)0.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.121 (3)0.082 (2)0.148 (3)0.027 (2)0.048 (3)0.034 (2)
C20.113 (3)0.078 (2)0.125 (3)−0.003 (2)0.058 (2)−0.029 (2)
C30.093 (2)0.111 (3)0.081 (2)−0.041 (2)0.0441 (18)−0.012 (2)
C40.082 (2)0.0693 (19)0.112 (2)−0.0142 (16)0.0286 (19)0.0015 (18)
C50.105 (3)0.081 (2)0.095 (2)−0.0020 (19)0.049 (2)−0.0140 (19)
C60.083 (2)0.0656 (18)0.098 (2)0.0009 (16)0.0235 (18)−0.0063 (17)
C70.116 (3)0.106 (2)0.073 (2)−0.028 (2)0.0178 (19)−0.0256 (19)
C80.086 (2)0.099 (2)0.0646 (17)−0.0261 (18)0.0367 (16)−0.0097 (16)
C90.075 (2)0.0583 (18)0.130 (3)−0.0048 (15)0.036 (2)−0.011 (2)
C100.0629 (18)0.0709 (18)0.0779 (18)0.0088 (15)0.0182 (14)0.0011 (15)
C110.0510 (17)0.082 (2)0.105 (2)−0.0047 (15)0.0185 (16)0.0027 (18)
C120.0568 (18)0.0676 (19)0.089 (2)0.0003 (14)0.0181 (15)−0.0017 (17)
C130.0553 (16)0.0637 (17)0.0768 (18)−0.0028 (13)0.0231 (14)−0.0080 (15)
C140.071 (2)0.0743 (18)0.0709 (18)−0.0194 (15)0.0154 (15)−0.0041 (15)
C150.0591 (17)0.0781 (19)0.0619 (15)−0.0067 (14)0.0207 (13)−0.0010 (15)
C160.0526 (16)0.0638 (16)0.0643 (15)0.0046 (13)0.0163 (12)0.0075 (13)
C170.0513 (16)0.0673 (18)0.0813 (19)0.0062 (14)0.0150 (14)−0.0084 (16)
C180.0653 (17)0.0625 (16)0.0514 (14)0.0017 (14)0.0142 (13)0.0037 (13)
C190.0539 (15)0.0601 (15)0.0508 (14)0.0007 (13)0.0175 (12)0.0066 (12)
C200.0523 (15)0.0650 (16)0.0519 (13)−0.0002 (13)0.0151 (12)0.0026 (13)
C210.0546 (16)0.0651 (16)0.0475 (13)−0.0021 (13)0.0151 (12)0.0028 (12)
C220.0566 (16)0.0722 (17)0.0446 (13)0.0030 (13)0.0170 (12)0.0015 (13)
N10.0553 (13)0.0680 (14)0.0620 (13)0.0058 (11)0.0129 (11)−0.0021 (12)
N20.0513 (13)0.0666 (13)0.0527 (11)−0.0026 (10)0.0157 (10)0.0019 (10)
O10.0954 (15)0.0916 (14)0.0620 (11)−0.0214 (12)0.0258 (10)−0.0159 (11)
O20.1142 (18)0.0841 (15)0.1000 (17)0.0303 (13)0.0250 (14)0.0171 (13)
O30.1182 (18)0.0836 (14)0.0708 (13)0.0356 (13)0.0233 (12)0.0012 (11)
O40.0820 (14)0.0921 (15)0.0601 (11)−0.0245 (11)0.0335 (10)−0.0087 (10)

Geometric parameters (Å, °)

C1—O21.410 (3)C10—H10A0.9700
C1—H1A0.9600C10—H10B0.9700
C1—H1B0.9600C11—C161.521 (3)
C1—H1C0.9600C11—H11A0.9700
C2—C51.363 (4)C11—H11B0.9700
C2—C91.378 (4)C12—O21.365 (3)
C2—H2A0.9300C12—C171.399 (4)
C3—C81.358 (4)C13—C171.396 (4)
C3—C141.377 (4)C13—C151.452 (4)
C3—H3A0.9300C14—C181.367 (3)
C4—C61.509 (4)C14—H14A0.9300
C4—C111.510 (4)C15—N11.269 (3)
C4—H4A0.9700C15—H15A0.9300
C4—H4B0.9700C16—N11.459 (3)
C5—C131.392 (4)C16—C201.522 (3)
C5—H5A0.9300C16—H16A0.9800
C6—C101.511 (4)C17—O31.346 (3)
C6—H6A0.9700C18—O11.371 (3)
C6—H6B0.9700C18—C191.392 (3)
C7—O11.425 (3)C19—O41.351 (3)
C7—H7A0.9600C19—C211.393 (3)
C7—H7B0.9600C20—N21.466 (3)
C7—H7C0.9600C20—H20A0.9800
C8—C211.397 (3)C21—C221.450 (3)
C8—H8A0.9300C22—N21.268 (3)
C9—C121.371 (4)C22—H22A0.9300
C9—H9A0.9300O3—H30.876 (18)
C10—C201.516 (3)O4—H40.86 (3)
O2—C1—H1A109.5C4—C11—H11B109.4
O2—C1—H1B109.5C16—C11—H11B109.4
H1A—C1—H1B109.5H11A—C11—H11B108.0
O2—C1—H1C109.5O2—C12—C9125.5 (3)
H1A—C1—H1C109.5O2—C12—C17114.9 (3)
H1B—C1—H1C109.5C9—C12—C17119.6 (3)
C5—C2—C9120.6 (3)C5—C13—C17119.1 (3)
C5—C2—H2A119.7C5—C13—C15120.5 (3)
C9—C2—H2A119.7C17—C13—C15120.4 (2)
C8—C3—C14121.0 (3)C18—C14—C3120.0 (3)
C8—C3—H3A119.5C18—C14—H14A120.0
C14—C3—H3A119.5C3—C14—H14A120.0
C6—C4—C11110.5 (2)N1—C15—C13122.2 (3)
C6—C4—H4A109.6N1—C15—H15A118.9
C11—C4—H4A109.6C13—C15—H15A118.9
C6—C4—H4B109.6N1—C16—C11109.8 (2)
C11—C4—H4B109.6N1—C16—C20108.3 (2)
H4A—C4—H4B108.1C11—C16—C20111.9 (2)
C2—C5—C13120.5 (3)N1—C16—H16A108.9
C2—C5—H5A119.8C11—C16—H16A108.9
C13—C5—H5A119.8C20—C16—H16A108.9
C4—C6—C10110.9 (2)O3—C17—C13121.7 (2)
C4—C6—H6A109.5O3—C17—C12118.5 (3)
C10—C6—H6A109.5C13—C17—C12119.7 (3)
C4—C6—H6B109.5C14—C18—O1125.0 (2)
C10—C6—H6B109.5C14—C18—C19120.0 (2)
H6A—C6—H6B108.0O1—C18—C19115.0 (2)
O1—C7—H7A109.5O4—C19—C18118.9 (2)
O1—C7—H7B109.5O4—C19—C21121.1 (2)
H7A—C7—H7B109.5C18—C19—C21120.0 (2)
O1—C7—H7C109.5N2—C20—C10111.1 (2)
H7A—C7—H7C109.5N2—C20—C16107.46 (19)
H7B—C7—H7C109.5C10—C20—C16111.4 (2)
C3—C8—C21120.3 (3)N2—C20—H20A108.9
C3—C8—H8A119.9C10—C20—H20A108.9
C21—C8—H8A119.9C16—C20—H20A108.9
C12—C9—C2120.5 (3)C19—C21—C8118.7 (2)
C12—C9—H9A119.8C19—C21—C22121.2 (2)
C2—C9—H9A119.8C8—C21—C22120.1 (2)
C6—C10—C20112.1 (2)N2—C22—C21122.4 (2)
C6—C10—H10A109.2N2—C22—H22A118.8
C20—C10—H10A109.2C21—C22—H22A118.8
C6—C10—H10B109.2C15—N1—C16119.8 (2)
C20—C10—H10B109.2C22—N2—C20119.2 (2)
H10A—C10—H10B107.9C18—O1—C7117.2 (2)
C4—C11—C16111.1 (2)C12—O2—C1118.4 (3)
C4—C11—H11A109.4C17—O3—H3107 (2)
C16—C11—H11A109.4C19—O4—H4106 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N10.88 (2)1.77 (2)2.572 (3)150 (3)
O4—H4···N20.86 (3)1.80 (3)2.587 (3)152 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5006).

References

  • Aslantaş, M., Tümer, M., Şahin, E. & Tümer, F. (2007). Acta Cryst. E63, o644–o645.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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.

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