2,6-Bis(2,4-dimethyl­benzyl­idene)cyclo­hexa­none

Solanko, K.A.; Bond, A.D.

doi:10.1107/S1600536810018684

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1435

https://doi.org/10.1107/S1600536810018684

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2,6-Bis(2,4-dimethylbenzylidene)cyclohexanone

Katarzyna A. Solanko ^a and Andrew D. Bond ^a ^*

^aUniversity of Southern Denmark, Department of Physics and Chemistry, Campusvej 55, 5230 Odense, Denmark
^*Correspondence e-mail: adb@chem.sdu.dk

(Received 17 May 2010; accepted 19 May 2010; online 22 May 2010)

In the crystal structure of the title compound, C₂₄H₆O, the molecule exhibits point symmetry m but the mirror plane is not utilized as part of the space-group symmetry. The structure contains face-to-face interactions between the 2,4-dimethylbenzylidene substituents in which the methyl groups lie directly above the centroids of adjacent benzene rings.

Related literature

For related structures, see: Guo et al. (2008 ); Jia et al. (1989 ); Liu (2009 ); Ompraba et al. (2003 ); Shi et al. (2008 ); Zhang et al. (2005 ); Zhou (2007 ). For quantification of the molecular point symmetry, see: Pilati & Forni (1998 , 2000 ).

Experimental

Crystal data

C₂₄H₂₆O
M_r = 330.45
Monoclinic, P 2₁ /c
a = 6.9784 (4) Å
b = 19.2540 (12) Å
c = 14.2829 (10) Å
β = 102.179 (3)°
V = 1875.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 120 K
0.60 × 0.20 × 0.20 mm

Data collection

Bruker–Nonius X8 APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.895, T_max = 0.986
32106 measured reflections
3565 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 1.08
3565 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
C—H⋯π interactions (Å, °)

Cg1 and Cg2 are the centroids of the C21–C26 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯Cg1ⁱ	0.98	3.00	3.532 (1)	154
C17—H17C⋯Cg1ⁱⁱ	0.98	2.62	3.469 (1)	111
C27—H27B⋯Cg2ⁱⁱⁱ	0.98	2.64	3.486 (1)	145
C27—H27C⋯Cg2^iv	0.98	2.80	3.510 (1)	130
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810018684/jh2159sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018684/jh2159Isup2.hkl

checkCIF report

Comment top

We were interested in the crystal structure of 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone (Guo et al., 2008) because we have found that it exhibits a relatively large change in structure on cooling from room temperature to 100 K (Solanko & Bond, unpublished results). We synthesised the analogous tetra-methyl-substituted compound to examine whether it might form a similar structure and display similar behaviour. It does not.

We note that in the publication of Guo et al. (2008), the chloro compound is stated to be synthesised by reaction of 2,4-dichlorobenzophenone with cyclohexanone. It seems likely that this should be 2,4-dichlorobenzaldehyde with cyclohexanone, as described here in the Experimental section.

The molecular point symmetry m referred to in the Abstract was quantified using the program SYMMOL (Pilati & Forni, 1998, 2000): the rms deviation of the molecule from its m symmetrised counterpart is 0.055 Å.

Related literature top

For related structures, see: Guo et al. (2008); Jia et al. (1989); Liu (2009); Ompraba et al. (2003); Shi et al. (2008); Zhang et al. (2005); Zhou (2007). For quantification of the molecular point symmetry, see: Pilati & Forni (1998, 2000).

Experimental top

2,4-Dimethylbenzaldehyde (2.8 ml, 0.02 mol), cyclohexanone (1.0 ml, 0.01 mol) and 30% NaOH(aq) (1 ml) were stirred in ethanol (3 ml) at room temperature for 6 h. The yellow product was filtered and washed using EtOH (3 × 2 ml). Crystals were obtained by slow evaporation from acetone under ambient conditions.

Structure description top

For related structures, see: Guo et al. (2008); Jia et al. (1989); Liu (2009); Ompraba et al. (2003); Shi et al. (2008); Zhang et al. (2005); Zhou (2007). For quantification of the molecular point symmetry, see: Pilati & Forni (1998, 2000).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular unit showing displacement ellipsoids at 50% probability. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Face-to-face interactions between the 2,4-dimethylbenzylidene substituents, with C(methyl)···centroid interactions highlighted.

2,6-Bis(2,4-dimethylbenzylidene)cyclohexanone top

Crystal data top

C₂₄H₂₆O	F(000) = 712
M_r = 330.45	D_x = 1.170 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5996 reflections
a = 6.9784 (4) Å	θ = 2.6–24.5°
b = 19.2540 (12) Å	µ = 0.07 mm⁻¹
c = 14.2829 (10) Å	T = 120 K
β = 102.179 (3)°	Needle, yellow
V = 1875.9 (2) Å³	0.60 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker–Nonius X8 APEXII CCD diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and φ scans	θ_max = 25.8°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→8
T_min = 0.895, T_max = 0.986	k = −19→23
32106 measured reflections	l = −17→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0604P)² + 0.133P] where P = (F_o² + 2F_c²)/3
3565 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₂₆O	V = 1875.9 (2) Å³
M_r = 330.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9784 (4) Å	µ = 0.07 mm⁻¹
b = 19.2540 (12) Å	T = 120 K
c = 14.2829 (10) Å	0.60 × 0.20 × 0.20 mm
β = 102.179 (3)°

Data collection top

Bruker–Nonius X8 APEXII CCD diffractometer	3565 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2399 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.986	R_int = 0.042
32106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
3565 reflections	Δρ_min = −0.22 e Å⁻³
230 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.0853 (2)	0.39396 (5)	0.26683 (9)	0.0545 (4)
C1	0.1796 (2)	0.39689 (7)	0.20350 (11)	0.0297 (4)
C2	0.2281 (2)	0.46589 (7)	0.16524 (10)	0.0243 (3)
C3	0.3539 (2)	0.46722 (7)	0.09156 (10)	0.0250 (4)
H3A	0.4324	0.5105	0.0989	0.030*
H3B	0.2687	0.4673	0.0267	0.030*
C4	0.4907 (2)	0.40496 (7)	0.10168 (11)	0.0274 (4)
H4A	0.5727	0.4074	0.0531	0.033*
H4B	0.5785	0.4051	0.1659	0.033*
C5	0.3697 (2)	0.33903 (7)	0.08813 (10)	0.0246 (4)
H5A	0.2836	0.3391	0.0234	0.030*
H5B	0.4583	0.2985	0.0924	0.030*
C6	0.24585 (19)	0.33209 (7)	0.16204 (10)	0.0226 (3)
C10	0.1637 (2)	0.52272 (7)	0.20284 (10)	0.0243 (4)
H10A	0.0927	0.5149	0.2518	0.029*
C11	0.18876 (19)	0.59566 (7)	0.17793 (10)	0.0205 (3)
C12	0.23238 (18)	0.64565 (7)	0.25081 (10)	0.0207 (3)
C13	0.25309 (18)	0.71416 (7)	0.22573 (10)	0.0215 (3)
H13A	0.2840	0.7477	0.2754	0.026*
C14	0.23096 (18)	0.73622 (7)	0.13169 (10)	0.0227 (3)
C15	0.18354 (19)	0.68668 (7)	0.05996 (10)	0.0225 (3)
H15A	0.1646	0.7003	−0.0053	0.027*
C16	0.16363 (19)	0.61763 (7)	0.08281 (10)	0.0217 (3)
H16A	0.1322	0.5844	0.0328	0.026*
C17	0.2599 (2)	0.62591 (8)	0.35419 (10)	0.0271 (4)
H17A	0.3140	0.6655	0.3944	0.041*
H17B	0.3505	0.5865	0.3677	0.041*
H17C	0.1332	0.6128	0.3682	0.041*
C18	0.2627 (2)	0.81108 (8)	0.11040 (11)	0.0330 (4)
H18A	0.2040	0.8406	0.1527	0.049*
H18B	0.2012	0.8211	0.0435	0.049*
H18C	0.4036	0.8205	0.1210	0.049*
C20	0.19241 (19)	0.27140 (7)	0.19475 (10)	0.0225 (3)
H20A	0.1265	0.2743	0.2464	0.027*
C21	0.22247 (18)	0.20107 (7)	0.16113 (9)	0.0198 (3)
C22	0.25798 (18)	0.14544 (7)	0.22633 (10)	0.0199 (3)
C23	0.27183 (19)	0.07907 (7)	0.19172 (10)	0.0247 (4)
H23A	0.2970	0.0417	0.2361	0.030*
C24	0.2504 (2)	0.06452 (8)	0.09459 (11)	0.0278 (4)
C25	0.2156 (2)	0.11958 (8)	0.03073 (11)	0.0268 (4)
H25A	0.2004	0.1113	−0.0360	0.032*
C26	0.20303 (19)	0.18648 (8)	0.06376 (10)	0.0239 (4)
H26A	0.1805	0.2236	0.0190	0.029*
C27	0.28382 (19)	0.15735 (8)	0.33191 (9)	0.0255 (4)
H27A	0.3023	0.1127	0.3655	0.038*
H27B	0.1671	0.1804	0.3450	0.038*
H27C	0.3990	0.1868	0.3543	0.038*
C28	0.2652 (3)	−0.00880 (8)	0.06076 (13)	0.0441 (5)
H28A	0.1693	−0.0379	0.0835	0.066*
H28B	0.3975	−0.0266	0.0861	0.066*
H28C	0.2384	−0.0097	−0.0094	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0908 (10)	0.0269 (7)	0.0671 (9)	−0.0005 (6)	0.0645 (8)	0.0014 (6)
C1	0.0368 (9)	0.0268 (10)	0.0313 (9)	−0.0015 (7)	0.0202 (7)	0.0008 (7)
C2	0.0257 (8)	0.0240 (9)	0.0256 (8)	0.0008 (6)	0.0105 (6)	0.0022 (7)
C3	0.0293 (8)	0.0223 (9)	0.0276 (8)	−0.0005 (6)	0.0154 (6)	0.0029 (6)
C4	0.0286 (8)	0.0266 (9)	0.0316 (9)	0.0009 (7)	0.0170 (7)	0.0030 (7)
C5	0.0292 (8)	0.0232 (9)	0.0242 (8)	0.0044 (6)	0.0117 (6)	0.0032 (6)
C6	0.0247 (8)	0.0225 (9)	0.0220 (8)	0.0002 (6)	0.0080 (6)	0.0012 (6)
C10	0.0251 (8)	0.0258 (9)	0.0255 (8)	0.0013 (6)	0.0130 (6)	0.0022 (7)
C11	0.0153 (7)	0.0233 (9)	0.0251 (9)	0.0033 (6)	0.0095 (6)	0.0033 (7)
C12	0.0127 (7)	0.0269 (9)	0.0231 (8)	0.0042 (6)	0.0055 (6)	0.0022 (7)
C13	0.0171 (7)	0.0232 (9)	0.0237 (8)	0.0020 (6)	0.0034 (6)	−0.0026 (6)
C14	0.0171 (7)	0.0229 (8)	0.0283 (9)	0.0038 (6)	0.0056 (6)	0.0047 (7)
C15	0.0203 (7)	0.0262 (9)	0.0217 (8)	0.0058 (6)	0.0062 (6)	0.0059 (7)
C16	0.0195 (7)	0.0249 (9)	0.0218 (8)	0.0027 (6)	0.0070 (6)	−0.0024 (6)
C17	0.0236 (8)	0.0331 (9)	0.0252 (8)	0.0007 (7)	0.0065 (6)	0.0032 (7)
C18	0.0369 (9)	0.0268 (9)	0.0350 (10)	0.0000 (7)	0.0071 (7)	0.0045 (7)
C20	0.0233 (7)	0.0252 (9)	0.0201 (8)	−0.0003 (6)	0.0071 (6)	0.0001 (6)
C21	0.0162 (7)	0.0220 (8)	0.0218 (8)	−0.0019 (6)	0.0051 (6)	−0.0016 (6)
C22	0.0115 (7)	0.0241 (9)	0.0245 (8)	−0.0026 (6)	0.0044 (6)	0.0000 (7)
C23	0.0170 (7)	0.0222 (9)	0.0353 (10)	−0.0009 (6)	0.0060 (6)	0.0031 (7)
C24	0.0190 (7)	0.0254 (9)	0.0401 (10)	−0.0016 (6)	0.0089 (7)	−0.0071 (8)
C25	0.0233 (8)	0.0324 (10)	0.0243 (8)	−0.0026 (7)	0.0044 (6)	−0.0078 (7)
C26	0.0212 (7)	0.0263 (9)	0.0241 (9)	−0.0010 (6)	0.0048 (6)	0.0003 (7)
C27	0.0223 (7)	0.0296 (9)	0.0248 (9)	−0.0024 (7)	0.0049 (6)	0.0038 (7)
C28	0.0447 (10)	0.0295 (10)	0.0590 (12)	−0.0009 (8)	0.0129 (9)	−0.0138 (9)

Geometric parameters (Å, º) top

O1—C1	1.2272 (17)	C16—H16A	0.950
C1—C6	1.4954 (19)	C17—H17A	0.980
C1—C2	1.5022 (19)	C17—H17B	0.980
C2—C10	1.3378 (19)	C17—H17C	0.980
C2—C3	1.5062 (19)	C18—H18A	0.980
C3—C4	1.5198 (19)	C18—H18B	0.980
C3—H3A	0.990	C18—H18C	0.980
C3—H3B	0.990	C20—C21	1.4665 (19)
C4—C5	1.5140 (19)	C20—H20A	0.950
C4—H4A	0.990	C21—C26	1.3970 (19)
C4—H4B	0.990	C21—C22	1.4067 (19)
C5—C6	1.5049 (19)	C22—C23	1.381 (2)
C5—H5A	0.990	C22—C27	1.4981 (19)
C5—H5B	0.990	C23—C24	1.392 (2)
C6—C20	1.3402 (18)	C23—H23A	0.950
C10—C11	1.4683 (19)	C24—C25	1.386 (2)
C10—H10A	0.950	C24—C28	1.503 (2)
C11—C16	1.3983 (19)	C25—C26	1.381 (2)
C11—C12	1.4033 (19)	C25—H25A	0.950
C12—C13	1.3824 (19)	C26—H26A	0.950
C12—C17	1.4973 (19)	C27—H27A	0.980
C13—C14	1.3858 (19)	C27—H27B	0.980
C13—H13A	0.950	C27—H27C	0.980
C14—C15	1.3878 (19)	C28—H28A	0.980
C14—C18	1.499 (2)	C28—H28B	0.980
C15—C16	1.3829 (19)	C28—H28C	0.980
C15—H15A	0.950

O1—C1—C6	120.80 (13)	C11—C16—H16A	119.3
O1—C1—C2	120.39 (13)	C12—C17—H17A	109.5
C6—C1—C2	118.80 (12)	C12—C17—H17B	109.5
C10—C2—C1	117.17 (12)	H17A—C17—H17B	109.5
C10—C2—C3	124.17 (12)	C12—C17—H17C	109.5
C1—C2—C3	118.58 (12)	H17A—C17—H17C	109.5
C2—C3—C4	111.52 (11)	H17B—C17—H17C	109.5
C2—C3—H3A	109.3	C14—C18—H18A	109.5
C4—C3—H3A	109.3	C14—C18—H18B	109.5
C2—C3—H3B	109.3	H18A—C18—H18B	109.5
C4—C3—H3B	109.3	C14—C18—H18C	109.5
H3A—C3—H3B	108.0	H18A—C18—H18C	109.5
C5—C4—C3	109.10 (12)	H18B—C18—H18C	109.5
C5—C4—H4A	109.9	C6—C20—C21	128.42 (13)
C3—C4—H4A	109.9	C6—C20—H20A	115.8
C5—C4—H4B	109.9	C21—C20—H20A	115.8
C3—C4—H4B	109.9	C26—C21—C22	118.20 (13)
H4A—C4—H4B	108.3	C26—C21—C20	121.40 (12)
C6—C5—C4	111.84 (11)	C22—C21—C20	120.25 (12)
C6—C5—H5A	109.2	C23—C22—C21	118.92 (13)
C4—C5—H5A	109.2	C23—C22—C27	119.96 (13)
C6—C5—H5B	109.2	C21—C22—C27	121.12 (12)
C4—C5—H5B	109.2	C22—C23—C24	122.82 (13)
H5A—C5—H5B	107.9	C22—C23—H23A	118.6
C20—C6—C1	117.23 (12)	C24—C23—H23A	118.6
C20—C6—C5	124.42 (12)	C25—C24—C23	117.97 (13)
C1—C6—C5	118.35 (11)	C25—C24—C28	121.41 (14)
C2—C10—C11	128.14 (13)	C23—C24—C28	120.61 (14)
C2—C10—H10A	115.9	C26—C25—C24	120.23 (14)
C11—C10—H10A	115.9	C26—C25—H25A	119.9
C16—C11—C12	118.44 (12)	C24—C25—H25A	119.9
C16—C11—C10	121.86 (13)	C25—C26—C21	121.85 (13)
C12—C11—C10	119.65 (12)	C25—C26—H26A	119.1
C13—C12—C11	118.72 (12)	C21—C26—H26A	119.1
C13—C12—C17	119.94 (13)	C22—C27—H27A	109.5
C11—C12—C17	121.33 (12)	C22—C27—H27B	109.5
C12—C13—C14	123.18 (13)	H27A—C27—H27B	109.5
C12—C13—H13A	118.4	C22—C27—H27C	109.5
C14—C13—H13A	118.4	H27A—C27—H27C	109.5
C13—C14—C15	117.73 (13)	H27B—C27—H27C	109.5
C13—C14—C18	120.01 (13)	C24—C28—H28A	109.5
C15—C14—C18	122.24 (13)	C24—C28—H28B	109.5
C16—C15—C14	120.44 (13)	H28A—C28—H28B	109.5
C16—C15—H15A	119.8	C24—C28—H28C	109.5
C14—C15—H15A	119.8	H28A—C28—H28C	109.5
C15—C16—C11	121.47 (13)	H28B—C28—H28C	109.5
C15—C16—H16A	119.3

O1—C1—C2—C10	−0.3 (2)	C12—C13—C14—C15	0.74 (19)
C6—C1—C2—C10	178.86 (13)	C12—C13—C14—C18	−177.85 (12)
O1—C1—C2—C3	176.57 (15)	C13—C14—C15—C16	−1.32 (19)
C6—C1—C2—C3	−4.3 (2)	C18—C14—C15—C16	177.24 (13)
C10—C2—C3—C4	148.79 (14)	C14—C15—C16—C11	0.5 (2)
C1—C2—C3—C4	−27.81 (19)	C12—C11—C16—C15	0.91 (19)
C2—C3—C4—C5	60.25 (16)	C10—C11—C16—C15	178.63 (12)
C3—C4—C5—C6	−60.88 (15)	C1—C6—C20—C21	174.29 (13)
O1—C1—C6—C20	2.1 (2)	C5—C6—C20—C21	−6.7 (2)
C2—C1—C6—C20	−177.03 (13)	C6—C20—C21—C26	−39.0 (2)
O1—C1—C6—C5	−176.96 (15)	C6—C20—C21—C22	145.61 (14)
C2—C1—C6—C5	3.9 (2)	C26—C21—C22—C23	−0.09 (18)
C4—C5—C6—C20	−150.24 (14)	C20—C21—C22—C23	175.44 (11)
C4—C5—C6—C1	28.73 (18)	C26—C21—C22—C27	178.95 (12)
C1—C2—C10—C11	−179.33 (13)	C20—C21—C22—C27	−5.52 (19)
C3—C2—C10—C11	4.0 (2)	C21—C22—C23—C24	−0.58 (19)
C2—C10—C11—C16	43.5 (2)	C27—C22—C23—C24	−179.63 (12)
C2—C10—C11—C12	−138.83 (15)	C22—C23—C24—C25	0.6 (2)
C16—C11—C12—C13	−1.47 (18)	C22—C23—C24—C28	−179.46 (13)
C10—C11—C12—C13	−179.23 (12)	C23—C24—C25—C26	0.0 (2)
C16—C11—C12—C17	179.60 (12)	C28—C24—C25—C26	−179.90 (13)
C10—C11—C12—C17	1.84 (19)	C24—C25—C26—C21	−0.7 (2)
C11—C12—C13—C14	0.66 (19)	C22—C21—C26—C25	0.71 (19)
C17—C12—C13—C14	179.61 (12)	C20—C21—C26—C25	−174.76 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C21–C26 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···Cg1ⁱ	0.98	3.00	3.532 (1)	154
C17—H17C···Cg1ⁱⁱ	0.98	2.62	3.469 (1)	111
C27—H27B···Cg2ⁱⁱⁱ	0.98	2.64	3.486 (1)	145
C27—H27C···Cg2^iv	0.98	2.80	3.510 (1)	130

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆O
M_r	330.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	6.9784 (4), 19.2540 (12), 14.2829 (10)
β (°)	102.179 (3)
V (Å³)	1875.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.60 × 0.20 × 0.20

Data collection
Diffractometer	Bruker–Nonius X8 APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.895, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	32106, 3565, 2399
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 1.08
No. of reflections	3565
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C21–C26 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···Cg1ⁱ	0.98	3.00	3.532 (1)	154.4
C17—H17C···Cg1ⁱⁱ	0.98	2.62	3.469 (1)	110.5
C27—H27B···Cg2ⁱⁱⁱ	0.98	2.64	3.486 (1)	145.0
C27—H27C···Cg2^iv	0.98	2.80	3.510 (1)	130.2

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2.

Acknowledgements

We are grateful to the Danish Natural Sciences Research Council for funding (grant No. 272-08-0237).

References

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