(2-Benzoyl­phen­yl)(3,4-dimethyl­phen­yl)methanone

Jagadeesan, G.; Sethusankar, K.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.

doi:10.1107/S1600536811029965

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2177

doi:10.1107/S1600536811029965

Open

access

(2-Benzoylphenyl)(3,4-dimethylphenyl)methanone

G. Jagadeesan,^a K. Sethusankar,^b ^* R. Sivasakthikumaran ^c and Arasambattu K. Mohanakrishnan ^c

^aDepartment of Physics, Dr MGR Educational and Research Institute University, Chennai 600 095, India, ^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 18 July 2011; accepted 25 July 2011; online 30 July 2011)

In the title compound, C₂₂H₁₈O₂, the central benzene ring forms dihedral angles of 76.0 (1) and 73.1 (1)° with the phenyl ring and dimethyl-substituted benzene ring, respectively. The carbonyl-group O atoms deviate significantly from the phenyl ring and the dimethyl-substituted benzene ring [−0.582 (12) and 0.546 (12) Å, respectively]. The crystal packing is stabilized by C—H⋯π interactions.

Related literature

For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978 ). For chelating reagents of metallic systems, see: Liang et al. (2003 ). For related bond-length and angle values, see: Judaš & Kaitner (2005). For related structures, see: Khan et al. (2009 ); Narayanan et al. (2011 ).

Experimental

Crystal data

C₂₂H₁₈O₂
M_r = 314.36
Monoclinic, P 2₁ /c
a = 17.8606 (14) Å
b = 7.7590 (6) Å
c = 11.9722 (11) Å
β = 93.942 (3)°
V = 1655.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
17270 measured reflections
3862 independent reflections
2827 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.129
S = 1.01
3862 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.93	2.86	3.747 (2)	159
C21—H21A⋯Cg3ⁱⁱ	0.96	2.91	3.8144 (17)	157
C22—H22C⋯Cg3ⁱⁱⁱ	0.96	2.78	3.6484 (17)	152
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029965/rk2286sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029965/rk2286Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029965/rk2286Isup3.cml

checkCIF report

Comment top

Diketones are important synthetic intermediates and starting materials in the synthesis of many heterocyclic compounds (Hirsch & Bailey, 1978) and also employed as effective chelating reagents for a large number of metallic systems (Liang et al., 2003).

X-ray analysis confirms the molecular structure and atom connectivity of the title compound as illustrated in the Fig. 1. The bond lengths and bond angles are normal and correspond to those observed in 2-benzyl-1,3-diphenylpropane-1,3-dione (Judaš & Kaitner, 2005). The central phenyl ring (C8–C13) of the compound forms dihedral angles of 76.0 (1)° and 73.1 (1)° with the other phenyl rings (C1–C6) and (C15–C20), respectively. The central phenyl ring (C8–C13) forms dihedral angles of 53.3 (6)° and 58.8 (6)° with the mean plane of the ketone groups (C13–C15/O1) and (C6–C8/O2), respectively.

In the dimethyl substituted phenyl ring (C15–C20) the deviation of atoms C21 and C22 are -0.014 (2) Å and -0.049 (2) Å, respectively. The atom O1 deviates by -0.582 (1) Å from the plane of the phenyl ring (C1–C6). Also the atom O2 deviate by 0.546 (1) Å from the plane of the phenyl ring (C15–C20). The title compound exhibits the structural similarities with the already reported related structures (Khan et al., 2009; Narayanan et al., 2011).

The molecular structure is stabilized by C—H···Cg interactions - look Table 1. The Cg1 is center of gravity of (C1–C6) ring and Cg3 is center of gravity of (C15–C20) ring. Symmetry codes: (i) -x, y - 1/2, -z + 5/2; (ii) -x + 1, y - 1/2, -z + 3/2; (iii) -x + 1, -y + 1, -z + 2.

Related literature top

For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978). For chelating reagents of metallic systems, see: Liang et al. (2003). For related bond-length and angle values, see: Judaš & Kaitner (2005). For related structures, see: Khan et al. (2009); Narayanan et al. (2011).

Experimental top

To a stirred suspension of 1-(3,4-dimethylphenyl)-3-phenyl-2-benzofuran (1 g, 3.22 mmol) in dry THF (20 ml), lead tetraacetate (1.52 g, 3.42 mmol) was added and refluxed at 343 K for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2 × 20 ml), washed with brine solution and dried (Na₂SO₄). The removal of solvent in vacuo afforded crude product. The crude product upon crystallization from methanol furnished the title compound as a colourless solid.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

(2-Benzoylphenyl)(3,4-dimethylphenyl)methanone top

Crystal data top

C₂₂H₁₈O₂	F(000) = 664
M_r = 314.36	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3862 reflections
a = 17.8606 (14) Å	θ = 2.3–27.7°
b = 7.7590 (6) Å	µ = 0.08 mm⁻¹
c = 11.9722 (11) Å	T = 295 K
β = 93.942 (3)°	Block, colourless
V = 1655.2 (2) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2827 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 27.7°, θ_min = 2.3°
ω scans	h = −23→21
17270 measured reflections	k = −10→10
3862 independent reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0581P)² + 0.4044P] where P = (F_o² + 2F_c²)/3
3862 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₂H₁₈O₂	V = 1655.2 (2) Å³
M_r = 314.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.8606 (14) Å	µ = 0.08 mm⁻¹
b = 7.7590 (6) Å	T = 295 K
c = 11.9722 (11) Å	0.30 × 0.25 × 0.20 mm
β = 93.942 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2827 reflections with I > 2σ(I)
17270 measured reflections	R_int = 0.030
3862 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
3862 reflections	Δρ_min = −0.18 e Å⁻³
219 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.05252 (9)	0.7620 (2)	1.04279 (14)	0.0501 (4)
H1	0.0669	0.8384	0.9884	0.060*
C2	−0.02238 (9)	0.7235 (3)	1.04997 (17)	0.0655 (5)
H2	−0.0582	0.7729	0.9998	0.079*
C3	−0.04421 (11)	0.6128 (3)	1.1308 (2)	0.0731 (6)
H3	−0.0948	0.5871	1.1354	0.088*
C4	0.00862 (12)	0.5398 (3)	1.20492 (18)	0.0722 (6)
H4	−0.0064	0.4659	1.2603	0.087*
C5	0.08396 (10)	0.5754 (2)	1.19788 (14)	0.0555 (4)
H5	0.1196	0.5245	1.2477	0.067*
C6	0.10627 (8)	0.68748 (18)	1.11613 (12)	0.0397 (3)
C7	0.18732 (8)	0.71909 (18)	1.10391 (11)	0.0375 (3)
C8	0.20890 (7)	0.88500 (17)	1.05002 (12)	0.0361 (3)
C9	0.19085 (8)	1.04058 (19)	1.09856 (14)	0.0481 (4)
H9	0.1628	1.0414	1.1612	0.058*
C10	0.21426 (9)	1.1940 (2)	1.05444 (17)	0.0579 (5)
H10	0.2032	1.2977	1.0887	0.070*
C11	0.25395 (9)	1.1945 (2)	0.95989 (18)	0.0607 (5)
H11	0.2678	1.2984	0.9285	0.073*
C12	0.27318 (8)	1.04049 (19)	0.91177 (15)	0.0516 (4)
H12	0.3010	1.0412	0.8489	0.062*
C13	0.25147 (7)	0.88492 (17)	0.95623 (12)	0.0377 (3)
C14	0.26870 (7)	0.71987 (17)	0.89837 (11)	0.0364 (3)
C15	0.34810 (7)	0.68460 (16)	0.87551 (11)	0.0338 (3)
C16	0.40683 (7)	0.74660 (17)	0.94594 (11)	0.0343 (3)
H16	0.3961	0.8163	1.0060	0.041*
C17	0.48140 (7)	0.70753 (16)	0.92943 (11)	0.0343 (3)
C18	0.49709 (8)	0.60617 (17)	0.83744 (11)	0.0363 (3)
C19	0.43783 (8)	0.54581 (18)	0.76678 (11)	0.0412 (3)
H19	0.4482	0.4791	0.7052	0.049*
C20	0.36435 (8)	0.58169 (18)	0.78516 (11)	0.0395 (3)
H20	0.3257	0.5375	0.7375	0.047*
C21	0.57643 (9)	0.5594 (2)	0.81499 (14)	0.0500 (4)
H21A	0.5760	0.4796	0.7537	0.075*
H21B	0.6007	0.5073	0.8806	0.075*
H21C	0.6032	0.6615	0.7964	0.075*
C22	0.54257 (9)	0.7725 (2)	1.00999 (13)	0.0472 (4)
H22A	0.5211	0.8371	1.0682	0.071*
H22B	0.5756	0.8454	0.9712	0.071*
H22C	0.5703	0.6767	1.0423	0.071*
O1	0.21870 (6)	0.61966 (14)	0.87004 (10)	0.0530 (3)
O2	0.23523 (6)	0.61759 (14)	1.13704 (10)	0.0545 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0392 (8)	0.0533 (9)	0.0576 (9)	−0.0033 (7)	0.0023 (7)	0.0058 (7)
C2	0.0382 (9)	0.0726 (12)	0.0846 (13)	−0.0041 (8)	−0.0035 (9)	0.0008 (10)
C3	0.0435 (10)	0.0785 (14)	0.0991 (15)	−0.0173 (9)	0.0185 (10)	−0.0055 (12)
C4	0.0656 (13)	0.0712 (13)	0.0830 (13)	−0.0172 (10)	0.0288 (11)	0.0111 (11)
C5	0.0547 (10)	0.0568 (10)	0.0560 (9)	−0.0037 (8)	0.0110 (8)	0.0100 (8)
C6	0.0370 (7)	0.0390 (7)	0.0436 (7)	−0.0022 (6)	0.0066 (6)	−0.0025 (6)
C7	0.0367 (7)	0.0368 (7)	0.0390 (7)	0.0029 (6)	0.0020 (6)	−0.0020 (6)
C8	0.0263 (6)	0.0331 (7)	0.0485 (8)	0.0009 (5)	−0.0004 (6)	−0.0019 (6)
C9	0.0377 (8)	0.0434 (8)	0.0630 (9)	0.0063 (6)	0.0033 (7)	−0.0088 (7)
C10	0.0392 (8)	0.0334 (8)	0.1004 (14)	0.0050 (7)	−0.0008 (9)	−0.0130 (8)
C11	0.0389 (8)	0.0320 (8)	0.1117 (15)	−0.0032 (7)	0.0077 (9)	0.0111 (9)
C12	0.0362 (8)	0.0408 (8)	0.0791 (11)	−0.0023 (6)	0.0132 (8)	0.0099 (8)
C13	0.0254 (6)	0.0340 (7)	0.0537 (8)	−0.0008 (5)	0.0035 (6)	0.0017 (6)
C14	0.0319 (7)	0.0358 (7)	0.0419 (7)	−0.0028 (6)	0.0048 (6)	0.0031 (6)
C15	0.0323 (7)	0.0313 (6)	0.0382 (7)	−0.0011 (5)	0.0046 (5)	0.0030 (5)
C16	0.0369 (7)	0.0321 (7)	0.0347 (6)	0.0004 (5)	0.0074 (5)	−0.0017 (5)
C17	0.0343 (7)	0.0320 (6)	0.0365 (7)	−0.0009 (5)	0.0027 (5)	0.0047 (5)
C18	0.0370 (7)	0.0336 (7)	0.0394 (7)	0.0045 (6)	0.0091 (6)	0.0066 (5)
C19	0.0477 (8)	0.0401 (8)	0.0366 (7)	0.0035 (6)	0.0080 (6)	−0.0057 (6)
C20	0.0397 (8)	0.0404 (7)	0.0381 (7)	−0.0031 (6)	0.0009 (6)	−0.0031 (6)
C21	0.0418 (8)	0.0538 (9)	0.0557 (9)	0.0106 (7)	0.0122 (7)	0.0022 (7)
C22	0.0397 (8)	0.0523 (9)	0.0489 (8)	−0.0027 (7)	−0.0023 (6)	−0.0010 (7)
O1	0.0388 (6)	0.0506 (7)	0.0701 (7)	−0.0122 (5)	0.0088 (5)	−0.0117 (5)
O2	0.0459 (6)	0.0471 (6)	0.0703 (7)	0.0103 (5)	0.0029 (5)	0.0112 (5)

Geometric parameters (Å, º) top

C1—C2	1.379 (2)	C12—C13	1.3853 (19)
C1—C6	1.382 (2)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.4980 (19)
C2—C3	1.371 (3)	C14—O1	1.2146 (16)
C2—H2	0.9300	C14—C15	1.4880 (18)
C3—C4	1.372 (3)	C15—C16	1.3861 (19)
C3—H3	0.9300	C15—C20	1.3911 (18)
C4—C5	1.382 (3)	C16—C17	1.3932 (18)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.388 (2)	C17—C18	1.3973 (18)
C5—H5	0.9300	C17—C22	1.494 (2)
C6—C7	1.4854 (19)	C18—C19	1.390 (2)
C7—O2	1.2095 (17)	C18—C21	1.5046 (19)
C7—C8	1.5020 (19)	C19—C20	1.374 (2)
C8—C9	1.3873 (19)	C19—H19	0.9300
C8—C13	1.399 (2)	C20—H20	0.9300
C9—C10	1.379 (2)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.376 (3)	C21—H21C	0.9600
C10—H10	0.9300	C22—H22A	0.9600
C11—C12	1.380 (2)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600

C2—C1—C6	120.27 (16)	C12—C13—C8	119.34 (13)
C2—C1—H1	119.9	C12—C13—C14	119.69 (13)
C6—C1—H1	119.9	C8—C13—C14	120.79 (12)
C3—C2—C1	120.25 (18)	O1—C14—C15	121.51 (12)
C3—C2—H2	119.9	O1—C14—C13	120.39 (12)
C1—C2—H2	119.9	C15—C14—C13	118.09 (11)
C2—C3—C4	119.92 (17)	C16—C15—C20	118.85 (12)
C2—C3—H3	120.0	C16—C15—C14	121.02 (12)
C4—C3—H3	120.0	C20—C15—C14	120.07 (12)
C3—C4—C5	120.49 (18)	C15—C16—C17	121.94 (12)
C3—C4—H4	119.8	C15—C16—H16	119.0
C5—C4—H4	119.8	C17—C16—H16	119.0
C4—C5—C6	119.76 (17)	C16—C17—C18	118.67 (12)
C4—C5—H5	120.1	C16—C17—C22	119.91 (12)
C6—C5—H5	120.1	C18—C17—C22	121.41 (13)
C1—C6—C5	119.30 (14)	C19—C18—C17	118.93 (12)
C1—C6—C7	120.48 (13)	C19—C18—C21	119.81 (13)
C5—C6—C7	120.13 (14)	C17—C18—C21	121.26 (13)
O2—C7—C6	122.17 (13)	C20—C19—C18	122.01 (13)
O2—C7—C8	120.16 (12)	C20—C19—H19	119.0
C6—C7—C8	117.67 (12)	C18—C19—H19	119.0
C9—C8—C13	119.44 (13)	C19—C20—C15	119.57 (13)
C9—C8—C7	119.47 (13)	C19—C20—H20	120.2
C13—C8—C7	120.94 (11)	C15—C20—H20	120.2
C10—C9—C8	120.37 (15)	C18—C21—H21A	109.5
C10—C9—H9	119.8	C18—C21—H21B	109.5
C8—C9—H9	119.8	H21A—C21—H21B	109.5
C11—C10—C9	120.26 (15)	C18—C21—H21C	109.5
C11—C10—H10	119.9	H21A—C21—H21C	109.5
C9—C10—H10	119.9	H21B—C21—H21C	109.5
C10—C11—C12	119.89 (15)	C17—C22—H22A	109.5
C10—C11—H11	120.1	C17—C22—H22B	109.5
C12—C11—H11	120.1	H22A—C22—H22B	109.5
C11—C12—C13	120.64 (15)	C17—C22—H22C	109.5
C11—C12—H12	119.7	H22A—C22—H22C	109.5
C13—C12—H12	119.7	H22B—C22—H22C	109.5

C6—C1—C2—C3	0.8 (3)	C7—C8—C13—C12	−177.13 (13)
C1—C2—C3—C4	0.0 (3)	C9—C8—C13—C14	−176.94 (13)
C2—C3—C4—C5	−0.8 (3)	C7—C8—C13—C14	7.6 (2)
C3—C4—C5—C6	0.8 (3)	C12—C13—C14—O1	−124.06 (16)
C2—C1—C6—C5	−0.8 (2)	C8—C13—C14—O1	51.2 (2)
C2—C1—C6—C7	175.82 (15)	C12—C13—C14—C15	55.03 (18)
C4—C5—C6—C1	0.0 (3)	C8—C13—C14—C15	−129.72 (14)
C4—C5—C6—C7	−176.65 (16)	O1—C14—C15—C16	−150.17 (14)
C1—C6—C7—O2	−153.93 (15)	C13—C14—C15—C16	30.75 (18)
C5—C6—C7—O2	22.7 (2)	O1—C14—C15—C20	27.0 (2)
C1—C6—C7—C8	27.09 (19)	C13—C14—C15—C20	−152.12 (13)
C5—C6—C7—C8	−156.27 (14)	C20—C15—C16—C17	−0.6 (2)
O2—C7—C8—C9	−118.70 (16)	C14—C15—C16—C17	176.55 (12)
C6—C7—C8—C9	60.30 (17)	C15—C16—C17—C18	1.55 (19)
O2—C7—C8—C13	56.75 (19)	C15—C16—C17—C22	−177.87 (13)
C6—C7—C8—C13	−124.25 (14)	C16—C17—C18—C19	−0.98 (19)
C13—C8—C9—C10	0.4 (2)	C22—C17—C18—C19	178.44 (13)
C7—C8—C9—C10	175.91 (14)	C16—C17—C18—C21	−179.98 (12)
C8—C9—C10—C11	1.8 (2)	C22—C17—C18—C21	−0.6 (2)
C9—C10—C11—C12	−2.8 (3)	C17—C18—C19—C20	−0.5 (2)
C10—C11—C12—C13	1.5 (3)	C21—C18—C19—C20	178.50 (13)
C11—C12—C13—C8	0.8 (2)	C18—C19—C20—C15	1.5 (2)
C11—C12—C13—C14	176.08 (15)	C16—C15—C20—C19	−0.9 (2)
C9—C8—C13—C12	−1.7 (2)	C14—C15—C20—C19	−178.09 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1ⁱ	0.93	2.86	3.747 (2)	159
C21—H21A···Cg3ⁱⁱ	0.96	2.91	3.8144 (17)	157
C22—H22C···Cg3ⁱⁱⁱ	0.96	2.78	3.6484 (17)	152

Symmetry codes: (i) −x, y−1/2, −z+5/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈O₂
M_r	314.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	17.8606 (14), 7.7590 (6), 11.9722 (11)
β (°)	93.942 (3)
V (Å³)	1655.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17270, 3862, 2827
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.129, 1.01
No. of reflections	3862
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1ⁱ	0.93	2.86	3.747 (2)	159
C21—H21A···Cg3ⁱⁱ	0.96	2.91	3.8144 (17)	157
C22—H22C···Cg3ⁱⁱⁱ	0.96	2.78	3.6484 (17)	152

Symmetry codes: (i) −x, y−1/2, −z+5/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2.

Acknowledgements

GJ and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection, and Dr V. Murugan, HOD, Department of Physics, for providing facilities in the department to carry out this work.

References

Bruker (2008). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hirsch, S. S. & Bailey, W. J. (1978). J. Org. Chem. 43, 4090-4094. CrossRef CAS Web of Science Google Scholar
Judaš, N. & Kaitner, B. (2005). Acta Cryst. E61, o4008–o4010. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Ng, S. W. (2009). Acta Cryst. E65, o2745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liang, F. S., Zhou, Q. G., Cheng, Y. X., Wang, L. X., Ma, D. G., Jing, X. B. & Wang, F. S. (2003). Chem. Mater. 15, 193–1937. Google Scholar
Narayanan, P., Sethusankar, K., Nandakumar, M. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o2120. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2177

doi:10.1107/S1600536811029965

Open

access