organic compounds
(2-Benzoylphenyl)(naphthalen-1-yl)methanone
aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: a_sp59@yahoo.in
In the title compound, C24H16O2, the naphthalene ring system makes dihedral angles of 78.5 (6) and 65.5 (7)° with the terminal and central benzene rings, respectively. The dihedral angle between the benzene rings is 74.5 (8)°. In the crystal, neighbouring molecules are interlinked through two C—H⋯π interactions, which construct a two-dimensional supramolecular framework extending infinitely along (010).
Related literature
For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998); Wright et al. (2000); Varma et al. (1994). For a related structure, see: Xia (2010).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell 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
https://doi.org/10.1107/S1600536812039098/bt6830sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039098/bt6830Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039098/bt6830Isup3.cml
To a stirred suspension of benzo[c]furan (2.38 g, 7.437 mmol) in dry THF (20 ml), lead tetraacetate (3.2 g, 7.437 mmol) was added and refluxed at 50°C for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2 x 20 ml), washed with brine solution and dried (Na2SO4). The removal of solvent in vacuo followed by crystallization from methanol afforded the title compound as a colorless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.
All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed at 0.93Å with Uiso(H) = 1.2Ueq(C).
Naphthalene derivatives have manifested applications in many fields, for example, as a colorant, explosive, disinfectant, insecticide and plant hormone auxin. Naphthalene is believed to play a role in the chemical defence against biological enemies (Wiltz et al., 1998; Wright et al., 2000). It may be produced by metabolic processes in termites or by associated microorganisms which inhabit, e.g., the termite guts (Varma et al., 1994).
Bond lengths and bond angles of the title compound are comparable with the related structure (Xia, 2010). The napthyl ring C15—C24 system makes dihedral angles of 78.5 (6)° and 65.5 (7)°, with the phenyl rings C1—C6 and the C8—C13 respectively.
The C–H···π interaction C11–H11—Cg1i (Cg1 : C1–C6) [symmetry code : (i) x-1/2, -y-1/2, z-1/2] links the adjacent title moleculesto generate an extended one dimensional supramolecular network along [104] direction. Parallely stacked [104] network are further linked through C20–H20···Cg2ii (Cg2 : C8–C13) [symmetry code : (i) x-1/2, -y-1/2, z-3/2] interaction to form a two dimensional supramolecular sheet extending parallel to the (010) plane.
For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998); Wright et al. (2000); Varma et al. (1994). For a related structure, see: Xia (2010).
Data collection: APEX2 (Bruker, 2008); cell
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).Fig. 1. The structure of showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level. |
C24H16O2 | F(000) = 704 |
Mr = 336.37 | Dx = 1.301 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4106 reflections |
a = 10.4105 (3) Å | θ = 2.1–27.9° |
b = 9.6218 (3) Å | µ = 0.08 mm−1 |
c = 17.8497 (5) Å | T = 293 K |
β = 106.113 (2)° | Block, white crystalline |
V = 1717.73 (9) Å3 | 0.25 × 0.22 × 0.19 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 4081 independent reflections |
Radiation source: fine-focus sealed tube | 2906 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω and φ scans | θmax = 27.9°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.980, Tmax = 0.985 | k = −9→12 |
18980 measured reflections | l = −23→22 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0682P)2 + 0.3208P] where P = (Fo2 + 2Fc2)/3 |
4081 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C24H16O2 | V = 1717.73 (9) Å3 |
Mr = 336.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.4105 (3) Å | µ = 0.08 mm−1 |
b = 9.6218 (3) Å | T = 293 K |
c = 17.8497 (5) Å | 0.25 × 0.22 × 0.19 mm |
β = 106.113 (2)° |
Bruker APEXII CCD area-detector diffractometer | 4081 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2906 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.985 | Rint = 0.024 |
18980 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.22 e Å−3 |
4081 reflections | Δρmin = −0.17 e Å−3 |
235 parameters |
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 | ||
C1 | −0.12964 (14) | 0.43758 (18) | 0.19247 (9) | 0.0514 (4) | |
H1 | −0.1978 | 0.4398 | 0.2168 | 0.062* | |
C2 | −0.11530 (16) | 0.54645 (18) | 0.14567 (10) | 0.0577 (4) | |
H2 | −0.1746 | 0.6209 | 0.1379 | 0.069* | |
C3 | −0.01362 (17) | 0.54578 (18) | 0.11029 (10) | 0.0572 (4) | |
H3 | −0.0030 | 0.6205 | 0.0795 | 0.069* | |
C4 | 0.07240 (15) | 0.43421 (16) | 0.12060 (9) | 0.0501 (4) | |
H4 | 0.1413 | 0.4341 | 0.0967 | 0.060* | |
C5 | 0.05740 (13) | 0.32213 (15) | 0.16614 (8) | 0.0410 (3) | |
C6 | −0.04434 (13) | 0.32506 (15) | 0.20384 (8) | 0.0417 (3) | |
C7 | −0.06077 (13) | 0.21477 (16) | 0.25979 (8) | 0.0451 (3) | |
C8 | 0.04444 (13) | 0.20243 (14) | 0.33523 (8) | 0.0404 (3) | |
C9 | 0.14254 (15) | 0.30231 (16) | 0.35969 (8) | 0.0482 (3) | |
H9 | 0.1457 | 0.3780 | 0.3278 | 0.058* | |
C10 | 0.23568 (17) | 0.28980 (18) | 0.43124 (10) | 0.0598 (4) | |
H10 | 0.3014 | 0.3574 | 0.4475 | 0.072* | |
C11 | 0.23221 (18) | 0.1786 (2) | 0.47854 (10) | 0.0635 (5) | |
H11 | 0.2953 | 0.1708 | 0.5268 | 0.076* | |
C12 | 0.13550 (18) | 0.0788 (2) | 0.45457 (10) | 0.0641 (5) | |
H12 | 0.1337 | 0.0028 | 0.4864 | 0.077* | |
C13 | 0.04130 (16) | 0.09075 (17) | 0.38380 (9) | 0.0534 (4) | |
H13 | −0.0250 | 0.0236 | 0.3683 | 0.064* | |
C14 | 0.14196 (13) | 0.19692 (15) | 0.17171 (8) | 0.0423 (3) | |
C15 | 0.26477 (13) | 0.20331 (15) | 0.14345 (9) | 0.0453 (3) | |
C16 | 0.25771 (14) | 0.16839 (14) | 0.06570 (9) | 0.0452 (3) | |
C17 | 0.13610 (17) | 0.13546 (16) | 0.00976 (9) | 0.0524 (4) | |
H17 | 0.0561 | 0.1393 | 0.0233 | 0.063* | |
C18 | 0.1356 (2) | 0.09810 (19) | −0.06394 (10) | 0.0701 (5) | |
H18 | 0.0556 | 0.0751 | −0.1004 | 0.084* | |
C19 | 0.2565 (3) | 0.0944 (2) | −0.08489 (13) | 0.0841 (7) | |
H19 | 0.2556 | 0.0689 | −0.1353 | 0.101* | |
C20 | 0.3734 (3) | 0.1272 (2) | −0.03286 (14) | 0.0783 (6) | |
H20 | 0.4520 | 0.1247 | −0.0480 | 0.094* | |
C21 | 0.37831 (17) | 0.16475 (16) | 0.04334 (11) | 0.0579 (4) | |
C22 | 0.49996 (17) | 0.1967 (2) | 0.10048 (15) | 0.0723 (6) | |
H22 | 0.5797 | 0.1944 | 0.0867 | 0.087* | |
C23 | 0.50251 (17) | 0.2301 (2) | 0.17366 (14) | 0.0743 (6) | |
H23 | 0.5835 | 0.2503 | 0.2099 | 0.089* | |
C24 | 0.38446 (16) | 0.2346 (2) | 0.19557 (11) | 0.0646 (5) | |
H24 | 0.3870 | 0.2592 | 0.2463 | 0.078* | |
O1 | −0.16245 (11) | 0.14676 (16) | 0.24595 (7) | 0.0731 (4) | |
O2 | 0.11301 (12) | 0.08900 (12) | 0.19794 (7) | 0.0604 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0423 (7) | 0.0617 (10) | 0.0521 (8) | 0.0068 (7) | 0.0164 (6) | −0.0069 (7) |
C2 | 0.0572 (9) | 0.0518 (10) | 0.0615 (9) | 0.0156 (7) | 0.0124 (7) | −0.0009 (7) |
C3 | 0.0655 (10) | 0.0477 (9) | 0.0583 (9) | 0.0072 (7) | 0.0172 (8) | 0.0105 (7) |
C4 | 0.0507 (8) | 0.0525 (9) | 0.0517 (8) | 0.0047 (7) | 0.0218 (7) | 0.0079 (7) |
C5 | 0.0373 (6) | 0.0465 (8) | 0.0399 (7) | 0.0021 (6) | 0.0120 (5) | 0.0020 (6) |
C6 | 0.0360 (6) | 0.0502 (8) | 0.0388 (7) | −0.0014 (6) | 0.0103 (5) | −0.0032 (6) |
C7 | 0.0365 (6) | 0.0554 (9) | 0.0476 (8) | −0.0056 (6) | 0.0185 (6) | −0.0028 (6) |
C8 | 0.0412 (7) | 0.0426 (8) | 0.0425 (7) | −0.0005 (6) | 0.0200 (6) | −0.0029 (6) |
C9 | 0.0515 (8) | 0.0450 (8) | 0.0476 (8) | −0.0047 (6) | 0.0131 (6) | 0.0007 (6) |
C10 | 0.0584 (9) | 0.0552 (10) | 0.0583 (9) | −0.0065 (8) | 0.0038 (7) | −0.0067 (8) |
C11 | 0.0658 (10) | 0.0691 (12) | 0.0497 (9) | 0.0113 (9) | 0.0062 (8) | 0.0034 (8) |
C12 | 0.0744 (11) | 0.0610 (11) | 0.0599 (10) | 0.0090 (9) | 0.0238 (8) | 0.0186 (8) |
C13 | 0.0558 (8) | 0.0488 (9) | 0.0608 (9) | −0.0050 (7) | 0.0246 (7) | 0.0036 (7) |
C14 | 0.0434 (7) | 0.0462 (8) | 0.0394 (7) | 0.0016 (6) | 0.0153 (6) | 0.0020 (6) |
C15 | 0.0395 (7) | 0.0442 (8) | 0.0551 (8) | 0.0067 (6) | 0.0178 (6) | 0.0075 (6) |
C16 | 0.0506 (8) | 0.0354 (7) | 0.0574 (8) | 0.0096 (6) | 0.0281 (7) | 0.0095 (6) |
C17 | 0.0641 (9) | 0.0451 (8) | 0.0517 (8) | 0.0049 (7) | 0.0221 (7) | 0.0061 (7) |
C18 | 0.1059 (15) | 0.0519 (10) | 0.0538 (9) | 0.0014 (10) | 0.0243 (10) | 0.0047 (8) |
C19 | 0.149 (2) | 0.0582 (12) | 0.0668 (12) | 0.0200 (13) | 0.0655 (14) | 0.0093 (9) |
C20 | 0.1069 (16) | 0.0585 (12) | 0.0952 (15) | 0.0211 (11) | 0.0707 (14) | 0.0163 (10) |
C21 | 0.0665 (10) | 0.0403 (8) | 0.0830 (11) | 0.0154 (7) | 0.0474 (9) | 0.0164 (8) |
C22 | 0.0474 (9) | 0.0612 (11) | 0.1210 (17) | 0.0115 (8) | 0.0445 (10) | 0.0251 (11) |
C23 | 0.0413 (8) | 0.0803 (14) | 0.0990 (15) | 0.0006 (9) | 0.0156 (9) | 0.0176 (11) |
C24 | 0.0485 (8) | 0.0747 (12) | 0.0677 (11) | 0.0003 (8) | 0.0114 (8) | 0.0080 (9) |
O1 | 0.0483 (6) | 0.0960 (10) | 0.0732 (8) | −0.0269 (6) | 0.0139 (5) | 0.0079 (7) |
O2 | 0.0730 (7) | 0.0453 (6) | 0.0755 (7) | 0.0027 (5) | 0.0415 (6) | 0.0069 (5) |
C1—C2 | 1.374 (2) | C12—H12 | 0.9300 |
C1—C6 | 1.379 (2) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—O2 | 1.2110 (17) |
C2—C3 | 1.375 (2) | C14—C15 | 1.5001 (18) |
C2—H2 | 0.9300 | C15—C24 | 1.366 (2) |
C3—C4 | 1.377 (2) | C15—C16 | 1.410 (2) |
C3—H3 | 0.9300 | C16—C17 | 1.414 (2) |
C4—C5 | 1.385 (2) | C16—C21 | 1.420 (2) |
C4—H4 | 0.9300 | C17—C18 | 1.362 (2) |
C5—C6 | 1.4039 (18) | C17—H17 | 0.9300 |
C5—C14 | 1.479 (2) | C18—C19 | 1.410 (3) |
C6—C7 | 1.499 (2) | C18—H18 | 0.9300 |
C7—O1 | 1.2101 (17) | C19—C20 | 1.347 (3) |
C7—C8 | 1.486 (2) | C19—H19 | 0.9300 |
C8—C9 | 1.382 (2) | C20—C21 | 1.395 (3) |
C8—C13 | 1.387 (2) | C20—H20 | 0.9300 |
C9—C10 | 1.378 (2) | C21—C22 | 1.422 (3) |
C9—H9 | 0.9300 | C22—C23 | 1.338 (3) |
C10—C11 | 1.370 (3) | C22—H22 | 0.9300 |
C10—H10 | 0.9300 | C23—C24 | 1.390 (2) |
C11—C12 | 1.371 (3) | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—C13 | 1.372 (2) | ||
C2—C1—C6 | 120.92 (14) | C12—C13—C8 | 120.36 (15) |
C2—C1—H1 | 119.5 | C12—C13—H13 | 119.8 |
C6—C1—H1 | 119.5 | C8—C13—H13 | 119.8 |
C1—C2—C3 | 120.22 (14) | O2—C14—C5 | 121.13 (12) |
C1—C2—H2 | 119.9 | O2—C14—C15 | 119.47 (13) |
C3—C2—H2 | 119.9 | C5—C14—C15 | 119.40 (12) |
C4—C3—C2 | 119.82 (15) | C24—C15—C16 | 120.76 (14) |
C4—C3—H3 | 120.1 | C24—C15—C14 | 118.79 (14) |
C2—C3—H3 | 120.1 | C16—C15—C14 | 120.31 (13) |
C3—C4—C5 | 120.67 (14) | C15—C16—C17 | 122.72 (13) |
C3—C4—H4 | 119.7 | C15—C16—C21 | 118.30 (14) |
C5—C4—H4 | 119.7 | C17—C16—C21 | 118.98 (14) |
C4—C5—C6 | 119.25 (13) | C18—C17—C16 | 120.26 (16) |
C4—C5—C14 | 120.77 (12) | C18—C17—H17 | 119.9 |
C6—C5—C14 | 119.89 (12) | C16—C17—H17 | 119.9 |
C1—C6—C5 | 119.07 (14) | C17—C18—C19 | 119.9 (2) |
C1—C6—C7 | 117.76 (12) | C17—C18—H18 | 120.1 |
C5—C6—C7 | 123.08 (12) | C19—C18—H18 | 120.1 |
O1—C7—C8 | 121.65 (14) | C20—C19—C18 | 120.89 (18) |
O1—C7—C6 | 120.12 (13) | C20—C19—H19 | 119.6 |
C8—C7—C6 | 117.94 (11) | C18—C19—H19 | 119.6 |
C9—C8—C13 | 119.01 (14) | C19—C20—C21 | 120.97 (18) |
C9—C8—C7 | 121.67 (13) | C19—C20—H20 | 119.5 |
C13—C8—C7 | 119.28 (13) | C21—C20—H20 | 119.5 |
C10—C9—C8 | 120.02 (15) | C20—C21—C16 | 119.00 (19) |
C10—C9—H9 | 120.0 | C20—C21—C22 | 122.68 (17) |
C8—C9—H9 | 120.0 | C16—C21—C22 | 118.31 (16) |
C11—C10—C9 | 120.49 (16) | C23—C22—C21 | 121.63 (15) |
C11—C10—H10 | 119.8 | C23—C22—H22 | 119.2 |
C9—C10—H10 | 119.8 | C21—C22—H22 | 119.2 |
C10—C11—C12 | 119.83 (16) | C22—C23—C24 | 120.17 (18) |
C10—C11—H11 | 120.1 | C22—C23—H23 | 119.9 |
C12—C11—H11 | 120.1 | C24—C23—H23 | 119.9 |
C11—C12—C13 | 120.28 (16) | C15—C24—C23 | 120.82 (18) |
C11—C12—H12 | 119.9 | C15—C24—H24 | 119.6 |
C13—C12—H12 | 119.9 | C23—C24—H24 | 119.6 |
C6—C1—C2—C3 | −1.1 (2) | C6—C5—C14—O2 | 11.4 (2) |
C1—C2—C3—C4 | 1.3 (3) | C4—C5—C14—C15 | 14.2 (2) |
C2—C3—C4—C5 | 0.2 (2) | C6—C5—C14—C15 | −169.37 (12) |
C3—C4—C5—C6 | −1.9 (2) | O2—C14—C15—C24 | −87.50 (19) |
C3—C4—C5—C14 | 174.57 (14) | C5—C14—C15—C24 | 93.24 (17) |
C2—C1—C6—C5 | −0.6 (2) | O2—C14—C15—C16 | 88.28 (18) |
C2—C1—C6—C7 | 176.10 (14) | C5—C14—C15—C16 | −90.98 (17) |
C4—C5—C6—C1 | 2.1 (2) | C24—C15—C16—C17 | −179.91 (15) |
C14—C5—C6—C1 | −174.38 (13) | C14—C15—C16—C17 | 4.4 (2) |
C4—C5—C6—C7 | −174.44 (13) | C24—C15—C16—C21 | 0.9 (2) |
C14—C5—C6—C7 | 9.1 (2) | C14—C15—C16—C21 | −174.84 (13) |
C1—C6—C7—O1 | 64.4 (2) | C15—C16—C17—C18 | −177.89 (15) |
C5—C6—C7—O1 | −118.96 (16) | C21—C16—C17—C18 | 1.3 (2) |
C1—C6—C7—C8 | −109.45 (15) | C16—C17—C18—C19 | −1.0 (3) |
C5—C6—C7—C8 | 67.15 (18) | C17—C18—C19—C20 | 0.1 (3) |
O1—C7—C8—C9 | −163.01 (15) | C18—C19—C20—C21 | 0.5 (3) |
C6—C7—C8—C9 | 10.8 (2) | C19—C20—C21—C16 | −0.1 (3) |
O1—C7—C8—C13 | 14.4 (2) | C19—C20—C21—C22 | 178.40 (18) |
C6—C7—C8—C13 | −171.76 (13) | C15—C16—C21—C20 | 178.49 (15) |
C13—C8—C9—C10 | 0.3 (2) | C17—C16—C21—C20 | −0.8 (2) |
C7—C8—C9—C10 | 177.73 (14) | C15—C16—C21—C22 | −0.1 (2) |
C8—C9—C10—C11 | 0.2 (2) | C17—C16—C21—C22 | −179.36 (14) |
C9—C10—C11—C12 | 0.1 (3) | C20—C21—C22—C23 | −178.77 (18) |
C10—C11—C12—C13 | −0.7 (3) | C16—C21—C22—C23 | −0.2 (3) |
C11—C12—C13—C8 | 1.2 (3) | C21—C22—C23—C24 | −0.2 (3) |
C9—C8—C13—C12 | −0.9 (2) | C16—C15—C24—C23 | −1.3 (3) |
C7—C8—C13—C12 | −178.45 (14) | C14—C15—C24—C23 | 174.46 (16) |
C4—C5—C14—O2 | −165.07 (14) | C22—C23—C24—C15 | 1.0 (3) |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···Cg1i | 0.93 | 2.71 | 3.618 (19) | 163 |
C20—H20···Cg2ii | 0.93 | 2.85 | 3.67 (3) | 141 |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y−1/2, z−3/2. |
Experimental details
Crystal data | |
Chemical formula | C24H16O2 |
Mr | 336.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 10.4105 (3), 9.6218 (3), 17.8497 (5) |
β (°) | 106.113 (2) |
V (Å3) | 1717.73 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.980, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18980, 4081, 2906 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.135, 1.01 |
No. of reflections | 4081 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.17 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···Cg1i | 0.93 | 2.71 | 3.618 (19) | 162.6 |
C20—H20···Cg2ii | 0.93 | 2.85 | 3.673 (30) | 140.5 |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y−1/2, z−3/2. |
Acknowledgements
GG and ASP thank Dr. Babu Varghese, SAIF, IIT, Chennai, India for the data collection.
References
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Naphthalene derivatives have manifested applications in many fields, for example, as a colorant, explosive, disinfectant, insecticide and plant hormone auxin. Naphthalene is believed to play a role in the chemical defence against biological enemies (Wiltz et al., 1998; Wright et al., 2000). It may be produced by metabolic processes in termites or by associated microorganisms which inhabit, e.g., the termite guts (Varma et al., 1994).
Bond lengths and bond angles of the title compound are comparable with the related structure (Xia, 2010). The napthyl ring C15—C24 system makes dihedral angles of 78.5 (6)° and 65.5 (7)°, with the phenyl rings C1—C6 and the C8—C13 respectively.
The C–H···π interaction C11–H11—Cg1i (Cg1 : C1–C6) [symmetry code : (i) x-1/2, -y-1/2, z-1/2] links the adjacent title moleculesto generate an extended one dimensional supramolecular network along [104] direction. Parallely stacked [104] network are further linked through C20–H20···Cg2ii (Cg2 : C8–C13) [symmetry code : (i) x-1/2, -y-1/2, z-3/2] interaction to form a two dimensional supramolecular sheet extending parallel to the (010) plane.