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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o928.
Published online 2009 March 31. doi:  10.1107/S160053680901112X
PMCID: PMC2968856

2,6-Bis(4-methoxy­benzyl­idene)cyclo­hexa­none

Abstract

In the title mol­ecule, C22H22O3, the central cyclo­hexa­none ring adopts an envelope conformation. The two outer aromatic rings form a dihedral angle of 19.3 (2)°. The crystal packing exhibits weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For background, see: Tanaka et al. (2000 [triangle]). For a related structure, see: Brinda, Mudakavi et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o928-scheme1.jpg

Experimental

Crystal data

  • C22H22O3
  • M r = 334.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o928-efi1.jpg
  • a = 9.0129 (8) Å
  • b = 9.4874 (10) Å
  • c = 20.9416 (17) Å
  • β = 100.518 (1)°
  • V = 1760.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.45 × 0.17 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.964, T max = 0.988
  • 9092 measured reflections
  • 3105 independent reflections
  • 1233 reflections with I > 2σ(I)
  • R int = 0.065

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.170
  • S = 0.87
  • 3105 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; 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: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901112X/cv2532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901112X/cv2532Isup2.hkl

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

Acknowledgments

This project was supported by the Foundation of Liaocheng Vocational and Technical College.

supplementary crystallographic information

Comment

The use of organic syntheses without volatile, often flammable, expensive and toxic solvents strongly reduces the waste production and many fundamental processes have proven to be achievable through efficient procedures characterized by high simplicity of set-up and work-up (Tanaka et al., 2000). In this paper, we describe a solvent-free protocol used in the synthesis of the title compound, (I), starting from the fragrant aldehydes and cyclohexanone in the presence of NaOH.

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in 4-methyl-2,6-bis(2-naphthylmethylene) cyclohexan-1-one (Brinda, Mudakavi et al., 2007). The central cyclohexanone ring adopts an envelope conformation. The mean planes of two rings - C8—C13 and C16—C21 - form a dihedral angle of 19.3 (2)°. The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

2-Methoxylbenzaldehyde (4 mmol) and cyclohexanone (2.0 mmol), NaOH (4.0 mmol) were mixed in 50 ml flash under sovlent-free condtions After stirring for 15 min at 293 K, tthe resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C22H22O3: C 79.02, H 6.63%; found: C 69.93, H 6.65%.

Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2–1.5Ueq(C).

Figures

Fig. 1.
View of (I) showing the atomic numbering scheme and 40% probability displacement ellipsoids.

Crystal data

C22H22O3F(000) = 712
Mr = 334.40Dx = 1.262 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.0129 (8) ÅCell parameters from 935 reflections
b = 9.4874 (10) Åθ = 2.4–25.2°
c = 20.9416 (17) ŵ = 0.08 mm1
β = 100.518 (1)°T = 298 K
V = 1760.6 (3) Å3Prism, yellow
Z = 40.45 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer3105 independent reflections
Radiation source: fine-focus sealed tube1233 reflections with I > 2σ(I)
graphiteRint = 0.065
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.964, Tmax = 0.988k = −11→11
9092 measured reflectionsl = −23→24

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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 0.87w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3
3105 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.12 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
O10.1376 (3)−0.1927 (3)0.02703 (11)0.1012 (9)
O20.4818 (3)−0.0038 (2)0.41111 (13)0.0905 (8)
O30.0867 (3)0.0536 (3)−0.35644 (17)0.1062 (9)
C10.1981 (4)−0.0760 (4)0.02660 (19)0.0782 (10)
C20.2658 (4)−0.0065 (3)0.0884 (2)0.0729 (10)
C30.3239 (4)0.1430 (3)0.08487 (18)0.0941 (12)
H3A0.30180.19630.12150.113*
H3B0.43270.14040.08830.113*
C40.2551 (5)0.2176 (4)0.02279 (19)0.1055 (14)
H4A0.14790.23050.02170.127*
H4B0.30070.31010.02200.127*
C50.2779 (5)0.1360 (4)−0.03590 (18)0.0973 (12)
H5A0.38510.1263−0.03590.117*
H5B0.23310.1869−0.07480.117*
C60.2063 (4)−0.0095 (3)−0.0364 (2)0.0754 (10)
C70.2725 (4)−0.0772 (3)0.1430 (2)0.0744 (10)
H70.2294−0.16620.13610.089*
C80.3302 (4)−0.0512 (3)0.21109 (18)0.0655 (9)
C90.4222 (4)0.0636 (4)0.2354 (2)0.0812 (10)
H90.44950.12910.20660.097*
C100.4728 (4)0.0810 (3)0.30125 (19)0.0760 (10)
H100.53260.15850.31580.091*
C110.4371 (4)−0.0127 (4)0.3454 (2)0.0746 (10)
C120.3475 (4)−0.1281 (3)0.3233 (2)0.0753 (10)
H120.3210−0.19320.35250.090*
C130.2984 (4)−0.1449 (3)0.2575 (2)0.0789 (10)
H130.2403−0.22380.24340.095*
C140.5918 (5)0.0992 (4)0.43567 (18)0.1055 (13)
H14A0.68290.08100.41940.158*
H14B0.61250.09510.48230.158*
H14C0.55450.19110.42200.158*
C150.1460 (4)−0.0755 (3)−0.0911 (2)0.0747 (10)
H150.1021−0.1614−0.08400.090*
C160.1343 (4)−0.0418 (3)−0.1593 (2)0.0709 (10)
C170.0221 (4)−0.1023 (3)−0.2053 (2)0.0777 (10)
H17−0.0428−0.1659−0.19070.093*
C18−0.0001 (4)−0.0757 (4)−0.2704 (2)0.0792 (10)
H18−0.0786−0.1184−0.29880.095*
C190.0973 (5)0.0166 (4)−0.2928 (2)0.0862 (12)
C200.2143 (5)0.0738 (4)−0.2494 (2)0.0884 (12)
H200.28230.1329−0.26460.106*
C210.2335 (4)0.0466 (4)−0.1850 (2)0.0894 (11)
H210.31420.0874−0.15720.107*
C22−0.0240 (5)−0.0063 (4)−0.4044 (2)0.1223 (16)
H22A−0.0036−0.1049−0.40820.184*
H22B−0.02310.0395−0.44520.184*
H22C−0.12130.0054−0.39250.184*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.117 (2)0.0614 (16)0.120 (2)−0.0281 (15)0.0088 (15)0.0043 (14)
O20.097 (2)0.0870 (18)0.087 (2)−0.0124 (15)0.0157 (15)0.0058 (14)
O30.128 (3)0.090 (2)0.104 (2)0.0029 (17)0.0314 (19)−0.0034 (17)
C10.072 (3)0.059 (2)0.105 (3)0.0060 (19)0.019 (2)0.008 (2)
C20.066 (2)0.053 (2)0.098 (3)−0.0002 (17)0.012 (2)−0.004 (2)
C30.107 (3)0.061 (2)0.109 (3)−0.011 (2)0.005 (2)0.003 (2)
C40.133 (4)0.053 (2)0.124 (3)−0.019 (2)0.005 (3)−0.003 (2)
C50.108 (3)0.063 (2)0.120 (3)−0.018 (2)0.017 (2)0.002 (2)
C60.070 (3)0.054 (2)0.101 (3)0.0013 (17)0.012 (2)−0.010 (2)
C70.065 (2)0.053 (2)0.107 (3)0.0008 (17)0.021 (2)0.001 (2)
C80.057 (2)0.047 (2)0.094 (3)0.0007 (17)0.018 (2)−0.0063 (19)
C90.078 (3)0.069 (2)0.101 (3)−0.010 (2)0.027 (2)0.010 (2)
C100.073 (3)0.064 (2)0.090 (3)−0.0117 (18)0.014 (2)0.002 (2)
C110.070 (3)0.067 (2)0.091 (3)0.0036 (19)0.025 (2)0.009 (2)
C120.071 (3)0.053 (2)0.104 (3)−0.0076 (18)0.022 (2)0.0050 (19)
C130.067 (3)0.056 (2)0.116 (3)−0.0037 (17)0.021 (2)0.000 (2)
C140.103 (3)0.083 (3)0.126 (3)−0.012 (2)0.008 (3)−0.008 (2)
C150.067 (2)0.059 (2)0.101 (3)0.0070 (18)0.022 (2)0.001 (2)
C160.060 (2)0.050 (2)0.104 (3)0.0043 (18)0.019 (2)−0.009 (2)
C170.072 (3)0.058 (2)0.106 (3)0.0068 (19)0.023 (2)−0.007 (2)
C180.073 (3)0.065 (2)0.101 (3)0.010 (2)0.021 (2)−0.008 (2)
C190.102 (4)0.065 (3)0.097 (4)0.026 (2)0.031 (3)0.001 (2)
C200.090 (3)0.069 (2)0.111 (4)−0.011 (2)0.031 (3)−0.010 (2)
C210.086 (3)0.076 (3)0.109 (4)−0.007 (2)0.023 (3)−0.009 (2)
C220.135 (4)0.134 (4)0.099 (3)0.024 (3)0.025 (3)−0.013 (3)

Geometric parameters (Å, °)

O1—C11.236 (4)C10—C111.363 (4)
O2—C111.364 (4)C10—H100.9300
O2—C141.420 (4)C11—C121.388 (4)
O3—C191.364 (4)C12—C131.377 (4)
O3—C221.400 (4)C12—H120.9300
C1—C61.477 (5)C13—H130.9300
C1—C21.481 (5)C14—H14A0.9600
C2—C71.318 (4)C14—H14B0.9600
C2—C31.518 (4)C14—H14C0.9600
C3—C41.510 (4)C15—C161.448 (4)
C3—H3A0.9700C15—H150.9300
C3—H3B0.9700C16—C171.388 (4)
C4—C51.498 (4)C16—C211.403 (5)
C4—H4A0.9700C17—C181.364 (4)
C4—H4B0.9700C17—H170.9300
C5—C61.523 (4)C18—C191.382 (5)
C5—H5A0.9700C18—H180.9300
C5—H5B0.9700C19—C201.372 (5)
C6—C151.330 (4)C20—C211.352 (5)
C7—C81.447 (4)C20—H200.9300
C7—H70.9300C21—H210.9300
C8—C131.385 (4)C22—H22A0.9600
C8—C91.407 (4)C22—H22B0.9600
C9—C101.380 (4)C22—H22C0.9600
C9—H90.9300
C11—O2—C14117.8 (3)C10—C11—C12118.9 (4)
C19—O3—C22120.6 (4)O2—C11—C12115.6 (3)
O1—C1—C6118.9 (3)C13—C12—C11119.0 (3)
O1—C1—C2120.3 (3)C13—C12—H12120.5
C6—C1—C2120.7 (4)C11—C12—H12120.5
C7—C2—C1118.6 (3)C12—C13—C8123.9 (3)
C7—C2—C3123.8 (3)C12—C13—H13118.0
C1—C2—C3117.6 (3)C8—C13—H13118.0
C4—C3—C2112.9 (3)O2—C14—H14A109.5
C4—C3—H3A109.0O2—C14—H14B109.5
C2—C3—H3A109.0H14A—C14—H14B109.5
C4—C3—H3B109.0O2—C14—H14C109.5
C2—C3—H3B109.0H14A—C14—H14C109.5
H3A—C3—H3B107.8H14B—C14—H14C109.5
C5—C4—C3111.6 (3)C6—C15—C16133.6 (3)
C5—C4—H4A109.3C6—C15—H15113.2
C3—C4—H4A109.3C16—C15—H15113.2
C5—C4—H4B109.3C17—C16—C21114.5 (4)
C3—C4—H4B109.3C17—C16—C15120.4 (4)
H4A—C4—H4B108.0C21—C16—C15125.0 (4)
C4—C5—C6110.7 (3)C18—C17—C16124.9 (4)
C4—C5—H5A109.5C18—C17—H17117.5
C6—C5—H5A109.5C16—C17—H17117.5
C4—C5—H5B109.5C17—C18—C19118.1 (4)
C6—C5—H5B109.5C17—C18—H18121.0
H5A—C5—H5B108.1C19—C18—H18121.0
C15—C6—C1119.3 (3)O3—C19—C20117.0 (4)
C15—C6—C5122.6 (3)O3—C19—C18124.0 (4)
C1—C6—C5118.1 (3)C20—C19—C18118.9 (4)
C2—C7—C8136.0 (3)C21—C20—C19121.9 (4)
C2—C7—H7112.0C21—C20—H20119.0
C8—C7—H7112.0C19—C20—H20119.0
C13—C8—C9115.2 (3)C20—C21—C16121.5 (4)
C13—C8—C7119.9 (3)C20—C21—H21119.3
C9—C8—C7124.8 (3)C16—C21—H21119.3
C10—C9—C8121.3 (3)O3—C22—H22A109.5
C10—C9—H9119.3O3—C22—H22B109.5
C8—C9—H9119.3H22A—C22—H22B109.5
C11—C10—C9121.6 (3)O3—C22—H22C109.5
C11—C10—H10119.2H22A—C22—H22C109.5
C9—C10—H10119.2H22B—C22—H22C109.5
C10—C11—O2125.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14B···O2i0.962.673.512 (5)146
C4—H4A···O1ii0.972.613.510 (5)154

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2532).

References

  • Brinda, Mudakavi, R., Chopra, D., Murthy, M. S. & Row, T. N. G. (2007). Acta Cryst. E63, o4494.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Tanaka, T. & Toda, F. (2000). Chem. Rev.100, 1025–1074. [PubMed]

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