2,6-Bis(4-methoxy-benzyl-idene)cyclo-hexa-none.

In the title mol-ecule, C(22)H(22)O(3), the central cyclo-hexa-none ring adopts an envelope conformation. The two outer aromatic rings form a dihedral angle of 19.3 (2)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C22H22O3

M = 334.40

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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: SHELXTL.

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

C22H22O3	F(000) = 712
Mr = 334.40	Dx = 1.262 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.0129 (8) Å	Cell parameters from 935 reflections
b = 9.4874 (10) Å	θ = 2.4–25.2°
c = 20.9416 (17) Å	µ = 0.08 mm−1
β = 100.518 (1)°	T = 298 K
V = 1760.6 (3) Å3	Prism, yellow
Z = 4	0.45 × 0.17 × 0.15 mm

Bruker SMART APEX CCD area-detector diffractometer	3105 independent reflections
Radiation source: fine-focus sealed tube	1233 reflections with I > 2σ(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.964, Tmax = 0.988	k = −11→11
9092 measured reflections	l = −23→24

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3
3105 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.12 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.1376 (3)	−0.1927 (3)	0.02703 (11)	0.1012 (9)
O2	0.4818 (3)	−0.0038 (2)	0.41111 (13)	0.0905 (8)
O3	0.0867 (3)	0.0536 (3)	−0.35644 (17)	0.1062 (9)
C1	0.1981 (4)	−0.0760 (4)	0.02660 (19)	0.0782 (10)
C2	0.2658 (4)	−0.0065 (3)	0.0884 (2)	0.0729 (10)
C3	0.3239 (4)	0.1430 (3)	0.08487 (18)	0.0941 (12)
H3A	0.3018	0.1963	0.1215	0.113*
H3B	0.4327	0.1404	0.0883	0.113*
C4	0.2551 (5)	0.2176 (4)	0.02279 (19)	0.1055 (14)
H4A	0.1479	0.2305	0.0217	0.127*
H4B	0.3007	0.3101	0.0220	0.127*
C5	0.2779 (5)	0.1360 (4)	−0.03590 (18)	0.0973 (12)
H5A	0.3851	0.1263	−0.0359	0.117*
H5B	0.2331	0.1869	−0.0748	0.117*
C6	0.2063 (4)	−0.0095 (3)	−0.0364 (2)	0.0754 (10)
C7	0.2725 (4)	−0.0772 (3)	0.1430 (2)	0.0744 (10)
H7	0.2294	−0.1662	0.1361	0.089*
C8	0.3302 (4)	−0.0512 (3)	0.21109 (18)	0.0655 (9)
C9	0.4222 (4)	0.0636 (4)	0.2354 (2)	0.0812 (10)
H9	0.4495	0.1291	0.2066	0.097*
C10	0.4728 (4)	0.0810 (3)	0.30125 (19)	0.0760 (10)
H10	0.5326	0.1585	0.3158	0.091*
C11	0.4371 (4)	−0.0127 (4)	0.3454 (2)	0.0746 (10)
C12	0.3475 (4)	−0.1281 (3)	0.3233 (2)	0.0753 (10)
H12	0.3210	−0.1932	0.3525	0.090*
C13	0.2984 (4)	−0.1449 (3)	0.2575 (2)	0.0789 (10)
H13	0.2403	−0.2238	0.2434	0.095*
C14	0.5918 (5)	0.0992 (4)	0.43567 (18)	0.1055 (13)
H14A	0.6829	0.0810	0.4194	0.158*
H14B	0.6125	0.0951	0.4823	0.158*
H14C	0.5545	0.1911	0.4220	0.158*
C15	0.1460 (4)	−0.0755 (3)	−0.0911 (2)	0.0747 (10)
H15	0.1021	−0.1614	−0.0840	0.090*
C16	0.1343 (4)	−0.0418 (3)	−0.1593 (2)	0.0709 (10)
C17	0.0221 (4)	−0.1023 (3)	−0.2053 (2)	0.0777 (10)
H17	−0.0428	−0.1659	−0.1907	0.093*
C18	−0.0001 (4)	−0.0757 (4)	−0.2704 (2)	0.0792 (10)
H18	−0.0786	−0.1184	−0.2988	0.095*
C19	0.0973 (5)	0.0166 (4)	−0.2928 (2)	0.0862 (12)
C20	0.2143 (5)	0.0738 (4)	−0.2494 (2)	0.0884 (12)
H20	0.2823	0.1329	−0.2646	0.106*
C21	0.2335 (4)	0.0466 (4)	−0.1850 (2)	0.0894 (11)
H21	0.3142	0.0874	−0.1572	0.107*
C22	−0.0240 (5)	−0.0063 (4)	−0.4044 (2)	0.1223 (16)
H22A	−0.0036	−0.1049	−0.4082	0.184*
H22B	−0.0231	0.0395	−0.4452	0.184*
H22C	−0.1213	0.0054	−0.3925	0.184*

	U11	U22	U33	U12	U13	U23
O1	0.117 (2)	0.0614 (16)	0.120 (2)	−0.0281 (15)	0.0088 (15)	0.0043 (14)
O2	0.097 (2)	0.0870 (18)	0.087 (2)	−0.0124 (15)	0.0157 (15)	0.0058 (14)
O3	0.128 (3)	0.090 (2)	0.104 (2)	0.0029 (17)	0.0314 (19)	−0.0034 (17)
C1	0.072 (3)	0.059 (2)	0.105 (3)	0.0060 (19)	0.019 (2)	0.008 (2)
C2	0.066 (2)	0.053 (2)	0.098 (3)	−0.0002 (17)	0.012 (2)	−0.004 (2)
C3	0.107 (3)	0.061 (2)	0.109 (3)	−0.011 (2)	0.005 (2)	0.003 (2)
C4	0.133 (4)	0.053 (2)	0.124 (3)	−0.019 (2)	0.005 (3)	−0.003 (2)
C5	0.108 (3)	0.063 (2)	0.120 (3)	−0.018 (2)	0.017 (2)	0.002 (2)
C6	0.070 (3)	0.054 (2)	0.101 (3)	0.0013 (17)	0.012 (2)	−0.010 (2)
C7	0.065 (2)	0.053 (2)	0.107 (3)	0.0008 (17)	0.021 (2)	0.001 (2)
C8	0.057 (2)	0.047 (2)	0.094 (3)	0.0007 (17)	0.018 (2)	−0.0063 (19)
C9	0.078 (3)	0.069 (2)	0.101 (3)	−0.010 (2)	0.027 (2)	0.010 (2)
C10	0.073 (3)	0.064 (2)	0.090 (3)	−0.0117 (18)	0.014 (2)	0.002 (2)
C11	0.070 (3)	0.067 (2)	0.091 (3)	0.0036 (19)	0.025 (2)	0.009 (2)
C12	0.071 (3)	0.053 (2)	0.104 (3)	−0.0076 (18)	0.022 (2)	0.0050 (19)
C13	0.067 (3)	0.056 (2)	0.116 (3)	−0.0037 (17)	0.021 (2)	0.000 (2)
C14	0.103 (3)	0.083 (3)	0.126 (3)	−0.012 (2)	0.008 (3)	−0.008 (2)
C15	0.067 (2)	0.059 (2)	0.101 (3)	0.0070 (18)	0.022 (2)	0.001 (2)
C16	0.060 (2)	0.050 (2)	0.104 (3)	0.0043 (18)	0.019 (2)	−0.009 (2)
C17	0.072 (3)	0.058 (2)	0.106 (3)	0.0068 (19)	0.023 (2)	−0.007 (2)
C18	0.073 (3)	0.065 (2)	0.101 (3)	0.010 (2)	0.021 (2)	−0.008 (2)
C19	0.102 (4)	0.065 (3)	0.097 (4)	0.026 (2)	0.031 (3)	0.001 (2)
C20	0.090 (3)	0.069 (2)	0.111 (4)	−0.011 (2)	0.031 (3)	−0.010 (2)
C21	0.086 (3)	0.076 (3)	0.109 (4)	−0.007 (2)	0.023 (3)	−0.009 (2)
C22	0.135 (4)	0.134 (4)	0.099 (3)	0.024 (3)	0.025 (3)	−0.013 (3)

O1—C1	1.236 (4)	C10—C11	1.363 (4)
O2—C11	1.364 (4)	C10—H10	0.9300
O2—C14	1.420 (4)	C11—C12	1.388 (4)
O3—C19	1.364 (4)	C12—C13	1.377 (4)
O3—C22	1.400 (4)	C12—H12	0.9300
C1—C6	1.477 (5)	C13—H13	0.9300
C1—C2	1.481 (5)	C14—H14A	0.9600
C2—C7	1.318 (4)	C14—H14B	0.9600
C2—C3	1.518 (4)	C14—H14C	0.9600
C3—C4	1.510 (4)	C15—C16	1.448 (4)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—C17	1.388 (4)
C4—C5	1.498 (4)	C16—C21	1.403 (5)
C4—H4A	0.9700	C17—C18	1.364 (4)
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.523 (4)	C18—C19	1.382 (5)
C5—H5A	0.9700	C18—H18	0.9300
C5—H5B	0.9700	C19—C20	1.372 (5)
C6—C15	1.330 (4)	C20—C21	1.352 (5)
C7—C8	1.447 (4)	C20—H20	0.9300
C7—H7	0.9300	C21—H21	0.9300
C8—C13	1.385 (4)	C22—H22A	0.9600
C8—C9	1.407 (4)	C22—H22B	0.9600
C9—C10	1.380 (4)	C22—H22C	0.9600
C9—H9	0.9300
C11—O2—C14	117.8 (3)	C10—C11—C12	118.9 (4)
C19—O3—C22	120.6 (4)	O2—C11—C12	115.6 (3)
O1—C1—C6	118.9 (3)	C13—C12—C11	119.0 (3)
O1—C1—C2	120.3 (3)	C13—C12—H12	120.5
C6—C1—C2	120.7 (4)	C11—C12—H12	120.5
C7—C2—C1	118.6 (3)	C12—C13—C8	123.9 (3)
C7—C2—C3	123.8 (3)	C12—C13—H13	118.0
C1—C2—C3	117.6 (3)	C8—C13—H13	118.0
C4—C3—C2	112.9 (3)	O2—C14—H14A	109.5
C4—C3—H3A	109.0	O2—C14—H14B	109.5
C2—C3—H3A	109.0	H14A—C14—H14B	109.5
C4—C3—H3B	109.0	O2—C14—H14C	109.5
C2—C3—H3B	109.0	H14A—C14—H14C	109.5
H3A—C3—H3B	107.8	H14B—C14—H14C	109.5
C5—C4—C3	111.6 (3)	C6—C15—C16	133.6 (3)
C5—C4—H4A	109.3	C6—C15—H15	113.2
C3—C4—H4A	109.3	C16—C15—H15	113.2
C5—C4—H4B	109.3	C17—C16—C21	114.5 (4)
C3—C4—H4B	109.3	C17—C16—C15	120.4 (4)
H4A—C4—H4B	108.0	C21—C16—C15	125.0 (4)
C4—C5—C6	110.7 (3)	C18—C17—C16	124.9 (4)
C4—C5—H5A	109.5	C18—C17—H17	117.5
C6—C5—H5A	109.5	C16—C17—H17	117.5
C4—C5—H5B	109.5	C17—C18—C19	118.1 (4)
C6—C5—H5B	109.5	C17—C18—H18	121.0
H5A—C5—H5B	108.1	C19—C18—H18	121.0
C15—C6—C1	119.3 (3)	O3—C19—C20	117.0 (4)
C15—C6—C5	122.6 (3)	O3—C19—C18	124.0 (4)
C1—C6—C5	118.1 (3)	C20—C19—C18	118.9 (4)
C2—C7—C8	136.0 (3)	C21—C20—C19	121.9 (4)
C2—C7—H7	112.0	C21—C20—H20	119.0
C8—C7—H7	112.0	C19—C20—H20	119.0
C13—C8—C9	115.2 (3)	C20—C21—C16	121.5 (4)
C13—C8—C7	119.9 (3)	C20—C21—H21	119.3
C9—C8—C7	124.8 (3)	C16—C21—H21	119.3
C10—C9—C8	121.3 (3)	O3—C22—H22A	109.5
C10—C9—H9	119.3	O3—C22—H22B	109.5
C8—C9—H9	119.3	H22A—C22—H22B	109.5
C11—C10—C9	121.6 (3)	O3—C22—H22C	109.5
C11—C10—H10	119.2	H22A—C22—H22C	109.5
C9—C10—H10	119.2	H22B—C22—H22C	109.5
C10—C11—O2	125.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2i	0.96	2.67	3.512 (5)	146
C4—H4A···O1ii	0.97	2.61	3.510 (5)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2i	0.96	2.67	3.512 (5)	146
C4—H4A⋯O1ii	0.97	2.61	3.510 (5)	154

Symmetry codes: (i) ; (ii) .