(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone

Kanchanadevi, J.; Anbalagan, G.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.; Gunasekaran, B.; Manivannan, V.

doi:10.1107/S1600536813018035

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1201

doi:10.1107/S1600536813018035

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(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone

J. Kanchanadevi,^a G. Anbalagan,^b R. Sivasakthikumaran,^c A. K. Mohanakrishnan,^c B. Gunasekaran ^d and V. Manivannan ^e ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, ^dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 14 June 2013; accepted 30 June 2013; online 3 July 2013)

The title compound C₂₈H₂₂O₂, basically consists of three ring systems, viz. a central benzene ring, with a lateral napthalene group to which it subtends a dihedral angle of 66.56 (4)° and a tetrahydropyran ring exhibiting a half-chair conformation. The molecular structure is stabilized by a weak intramolecular C—H⋯O interaction, while the crystal packing features weak C—H⋯π contacts.

Related literature

For the biological activity of diketones, see: Bennett et al. (1999 ); Sugawara et al. (2001 ). For related structures, see: Jagadeesan et al. (2011 , 2013 )

Experimental

Crystal data

C₂₈H₂₂O₂
M_r = 390.46
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.5625 (5) Å
b = 13.6374 (8) Å
c = 14.4927 (8) Å
V = 2087.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.989
13047 measured reflections
4998 independent reflections
3511 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.100
S = 1.03
4998 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1	0.93	2.29	2.856 (2)	118
C4—H4⋯Cg3ⁱ	0.93	2.54	3.419 (1)	159
C25—H25A⋯Cg3ⁱⁱ	0.97	2.94	3.849 (5)	157
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018035/bg2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018035/bg2509Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018035/bg2509Isup3.cml

checkCIF report

Comment top

In recent days diketones and their derivatives are very important on account of their wide range of applications in biology and medicine. They are known to exhibit antioxidant, antitumour and antibacterial activities (Bennett et al., 1999). Also they are useful as hematopoietic agents in medicine, in particular, in the treatment of cancer, chemotherapy, radiotherapy and drug therapy (Sugawara et al., 2001).

The geometric parameters of the title molecule (Fig. 1) agree well with those of reported similar structures (Jagadeesan et al., 2011, 2013). The central phenyl ring (C1—C6) makes a dihedral angle of 66.56 (4) ° with the napthelene ring (C8—C17) system, while the tetrahydropyran ring exhibits a half-chair conformation.

The molecular structure is stabilized by a weak intramolecular a C—H···O interaction and the crystal packing is controlled by weak C—H···π contacts (Table 1).

Related literature top

For the biological activity of diketones, see: Bennett et al. (1999); Sugawara et al. (2001). For related structures, see: Jagadeesan et al. (2011, 2013)

Experimental top

To a stirred solution of benzo[c]furan (1.0 g, 2.67 mmol) in dry THF (20 ml), lead tetraacetate (LTA) (1.18 g, 2.66 mmol) was added and then stirred 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). Removal of solvent in vacuum followed by crystallization from methanol furnished the compound as a colourless solid with a Yield of 94%.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone top

Crystal data top

C₂₈H₂₂O₂	F(000) = 824
M_r = 390.46	D_x = 1.242 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5023 reflections
a = 10.5625 (5) Å	θ = 2.4–27.9°
b = 13.6374 (8) Å	µ = 0.08 mm⁻¹
c = 14.4927 (8) Å	T = 295 K
V = 2087.6 (2) Å³	Block, colourless
Z = 4	0.20 × 0.18 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	4998 independent reflections
Radiation source: fine-focus sealed tube	3511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0 pixels mm^-1	θ_max = 28.0°, θ_min = 2.4°
ω and ϕ scans	h = −13→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→11
T_min = 0.985, T_max = 0.989	l = −19→19
13047 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0423P)² + 0.1006P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4998 reflections	Δρ_max = 0.14 e Å⁻³
272 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (11)

Crystal data top

C₂₈H₂₂O₂	V = 2087.6 (2) Å³
M_r = 390.46	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.5625 (5) Å	µ = 0.08 mm⁻¹
b = 13.6374 (8) Å	T = 295 K
c = 14.4927 (8) Å	0.20 × 0.18 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	4998 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3511 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.989	R_int = 0.027
13047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.14 e Å⁻³
4998 reflections	Δρ_min = −0.13 e Å⁻³
272 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.33655 (16)	0.99371 (12)	0.82430 (11)	0.0415 (4)
C2	0.32842 (16)	0.98524 (12)	0.92015 (11)	0.0412 (4)
C3	0.23477 (17)	1.03566 (13)	0.96667 (13)	0.0490 (4)
H3	0.2288	1.0302	1.0305	0.059*
C4	0.15021 (18)	1.09395 (15)	0.91969 (15)	0.0579 (5)
H4	0.0873	1.1273	0.9519	0.070*
C5	0.15820 (18)	1.10309 (15)	0.82597 (15)	0.0569 (5)
H5	0.1011	1.1428	0.7944	0.068*
C6	0.25110 (17)	1.05336 (13)	0.77827 (13)	0.0517 (5)
H6	0.2565	1.0599	0.7145	0.062*
C7	0.42627 (17)	0.92891 (14)	0.77308 (12)	0.0476 (4)
C8	0.49710 (16)	0.96879 (13)	0.69309 (12)	0.0439 (4)
C9	0.52520 (18)	1.06701 (14)	0.69107 (14)	0.0543 (5)
H9	0.4900	1.1078	0.7357	0.065*
C10	0.6045 (2)	1.10767 (16)	0.62462 (15)	0.0643 (5)
H10	0.6202	1.1748	0.6243	0.077*
C11	0.6585 (2)	1.04903 (16)	0.56068 (14)	0.0618 (5)
H11	0.7140	1.0761	0.5179	0.074*
C12	0.63253 (16)	0.94787 (15)	0.55742 (12)	0.0498 (5)
C13	0.68928 (19)	0.88731 (19)	0.49028 (14)	0.0655 (6)
H13	0.7459	0.9141	0.4481	0.079*
C14	0.6619 (2)	0.79030 (19)	0.48681 (16)	0.0733 (7)
H14	0.7003	0.7509	0.4425	0.088*
C15	0.5770 (2)	0.74932 (16)	0.54904 (15)	0.0669 (6)
H15	0.5578	0.6829	0.5451	0.080*
C16	0.52150 (17)	0.80499 (13)	0.61565 (13)	0.0522 (5)
H16	0.4647	0.7762	0.6565	0.063*
C17	0.54892 (14)	0.90562 (13)	0.62354 (12)	0.0424 (4)
C18	0.42905 (17)	0.93173 (14)	0.97279 (12)	0.0446 (4)
C19	0.39317 (16)	0.85114 (13)	1.03589 (11)	0.0413 (4)
C20	0.48595 (17)	0.80906 (14)	1.09093 (12)	0.0476 (4)
H20	0.5684	0.8328	1.0874	0.057*
C21	0.45937 (17)	0.73290 (14)	1.15083 (12)	0.0504 (5)
C22	0.5631 (2)	0.6889 (2)	1.20877 (15)	0.0760 (7)
H22A	0.6168	0.7412	1.2317	0.091*
H22B	0.6147	0.6468	1.1701	0.091*
C23	0.5145 (3)	0.62984 (19)	1.28973 (16)	0.0862 (8)
H23A	0.5833	0.5917	1.3158	0.103*
H23B	0.4835	0.6740	1.3371	0.103*
C24	0.4094 (3)	0.5620 (2)	1.26035 (19)	0.0970 (9)
H24A	0.4404	0.5177	1.2131	0.116*
H24B	0.3823	0.5229	1.3127	0.116*
C25	0.2995 (2)	0.61887 (17)	1.22370 (17)	0.0791 (7)
H25A	0.2545	0.6482	1.2751	0.095*
H25B	0.2418	0.5739	1.1933	0.095*
C26	0.33552 (19)	0.69868 (14)	1.15654 (12)	0.0512 (5)
C27	0.24312 (18)	0.74029 (14)	1.10116 (13)	0.0519 (5)
H27	0.1605	0.7170	1.1047	0.062*
C28	0.27079 (17)	0.81506 (13)	1.04115 (12)	0.0468 (4)
H28	0.2075	0.8415	1.0041	0.056*
O1	0.44000 (15)	0.84526 (11)	0.79968 (10)	0.0732 (4)
O2	0.53817 (12)	0.95838 (12)	0.96392 (11)	0.0726 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (10)	0.0393 (10)	0.0415 (9)	−0.0032 (8)	0.0041 (7)	0.0052 (8)
C2	0.0430 (9)	0.0389 (10)	0.0416 (9)	−0.0055 (8)	0.0013 (7)	0.0034 (7)
C3	0.0545 (11)	0.0479 (11)	0.0446 (10)	0.0008 (9)	0.0094 (8)	0.0021 (8)
C4	0.0523 (11)	0.0541 (12)	0.0674 (13)	0.0082 (10)	0.0130 (9)	0.0033 (10)
C5	0.0513 (12)	0.0507 (12)	0.0688 (13)	0.0109 (9)	−0.0017 (9)	0.0126 (10)
C6	0.0575 (11)	0.0524 (12)	0.0453 (10)	0.0011 (9)	−0.0028 (9)	0.0104 (9)
C7	0.0552 (11)	0.0437 (11)	0.0438 (10)	0.0001 (9)	0.0037 (8)	0.0060 (8)
C8	0.0478 (10)	0.0430 (10)	0.0409 (9)	0.0035 (8)	0.0012 (7)	0.0055 (8)
C9	0.0651 (12)	0.0444 (11)	0.0535 (11)	−0.0031 (9)	0.0090 (9)	0.0008 (9)
C10	0.0758 (13)	0.0477 (12)	0.0693 (13)	−0.0124 (10)	0.0153 (12)	0.0074 (11)
C11	0.0614 (12)	0.0649 (14)	0.0590 (13)	−0.0073 (11)	0.0136 (10)	0.0149 (10)
C12	0.0450 (10)	0.0607 (13)	0.0436 (10)	0.0060 (9)	0.0009 (7)	0.0061 (9)
C13	0.0587 (12)	0.0831 (18)	0.0547 (12)	0.0140 (11)	0.0094 (10)	0.0021 (11)
C14	0.0760 (15)	0.0790 (18)	0.0649 (14)	0.0293 (13)	0.0060 (11)	−0.0137 (13)
C15	0.0809 (15)	0.0487 (13)	0.0710 (15)	0.0172 (11)	−0.0036 (12)	−0.0058 (11)
C16	0.0599 (11)	0.0448 (11)	0.0519 (11)	0.0078 (9)	−0.0016 (9)	0.0069 (9)
C17	0.0410 (9)	0.0454 (10)	0.0406 (9)	0.0045 (7)	−0.0052 (7)	0.0055 (8)
C18	0.0431 (10)	0.0488 (11)	0.0420 (9)	−0.0021 (8)	0.0002 (7)	0.0033 (8)
C19	0.0457 (9)	0.0416 (10)	0.0367 (8)	−0.0001 (8)	0.0023 (7)	−0.0019 (8)
C20	0.0447 (10)	0.0544 (11)	0.0435 (9)	0.0010 (9)	0.0018 (7)	0.0038 (8)
C21	0.0591 (12)	0.0530 (11)	0.0391 (10)	0.0101 (9)	0.0075 (8)	0.0043 (8)
C22	0.0740 (14)	0.0879 (18)	0.0661 (14)	0.0233 (13)	0.0023 (11)	0.0249 (13)
C23	0.110 (2)	0.0872 (19)	0.0611 (14)	0.0355 (17)	0.0091 (14)	0.0274 (13)
C24	0.121 (2)	0.0741 (18)	0.096 (2)	0.0233 (17)	0.0315 (17)	0.0412 (16)
C25	0.0948 (17)	0.0636 (15)	0.0790 (16)	0.0071 (12)	0.0311 (13)	0.0268 (13)
C26	0.0633 (13)	0.0432 (11)	0.0470 (10)	0.0069 (9)	0.0173 (8)	0.0028 (8)
C27	0.0516 (10)	0.0483 (11)	0.0560 (11)	−0.0068 (9)	0.0096 (9)	−0.0019 (9)
C28	0.0500 (10)	0.0472 (11)	0.0432 (10)	−0.0014 (8)	0.0000 (8)	−0.0009 (8)
O1	0.1049 (12)	0.0478 (8)	0.0669 (9)	0.0165 (8)	0.0289 (8)	0.0166 (7)
O2	0.0455 (8)	0.0879 (11)	0.0844 (10)	−0.0111 (7)	−0.0058 (7)	0.0355 (9)

Geometric parameters (Å, º) top

C1—C6	1.386 (2)	C15—C16	1.361 (3)
C1—C2	1.397 (2)	C15—H15	0.9300
C1—C7	1.493 (2)	C16—C17	1.407 (2)
C2—C3	1.380 (2)	C16—H16	0.9300
C2—C18	1.498 (2)	C18—O2	1.215 (2)
C3—C4	1.376 (3)	C18—C19	1.479 (2)
C3—H3	0.9300	C19—C28	1.385 (2)
C4—C5	1.367 (3)	C19—C20	1.388 (2)
C4—H4	0.9300	C20—C21	1.382 (2)
C5—C6	1.379 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C26	1.391 (3)
C6—H6	0.9300	C21—C22	1.505 (3)
C7—O1	1.213 (2)	C22—C23	1.513 (3)
C7—C8	1.483 (2)	C22—H22A	0.9700
C8—C9	1.372 (2)	C22—H22B	0.9700
C8—C17	1.435 (2)	C23—C24	1.507 (4)
C9—C10	1.392 (3)	C23—H23A	0.9700
C9—H9	0.9300	C23—H23B	0.9700
C10—C11	1.350 (3)	C24—C25	1.494 (3)
C10—H10	0.9300	C24—H24A	0.9700
C11—C12	1.407 (3)	C24—H24B	0.9700
C11—H11	0.9300	C25—C26	1.509 (3)
C12—C13	1.410 (3)	C25—H25A	0.9700
C12—C17	1.425 (2)	C25—H25B	0.9700
C13—C14	1.355 (3)	C26—C27	1.385 (3)
C13—H13	0.9300	C27—C28	1.372 (2)
C14—C15	1.389 (3)	C27—H27	0.9300
C14—H14	0.9300	C28—H28	0.9300

C6—C1—C2	119.15 (17)	C16—C17—C12	117.86 (17)
C6—C1—C7	121.42 (16)	C16—C17—C8	124.35 (16)
C2—C1—C7	118.98 (16)	C12—C17—C8	117.79 (16)
C3—C2—C1	119.25 (16)	O2—C18—C19	122.04 (16)
C3—C2—C18	120.16 (15)	O2—C18—C2	118.26 (16)
C1—C2—C18	120.21 (16)	C19—C18—C2	119.67 (15)
C4—C3—C2	120.75 (17)	C28—C19—C20	118.71 (16)
C4—C3—H3	119.6	C28—C19—C18	122.48 (15)
C2—C3—H3	119.6	C20—C19—C18	118.80 (15)
C5—C4—C3	120.29 (18)	C21—C20—C19	121.89 (16)
C5—C4—H4	119.9	C21—C20—H20	119.1
C3—C4—H4	119.9	C19—C20—H20	119.1
C4—C5—C6	119.83 (18)	C20—C21—C26	118.70 (16)
C4—C5—H5	120.1	C20—C21—C22	120.15 (18)
C6—C5—H5	120.1	C26—C21—C22	121.15 (17)
C5—C6—C1	120.72 (17)	C21—C22—C23	113.45 (19)
C5—C6—H6	119.6	C21—C22—H22A	108.9
C1—C6—H6	119.6	C23—C22—H22A	108.9
O1—C7—C8	122.21 (16)	C21—C22—H22B	108.9
O1—C7—C1	118.32 (15)	C23—C22—H22B	108.9
C8—C7—C1	119.45 (16)	H22A—C22—H22B	107.7
C9—C8—C17	119.25 (16)	C24—C23—C22	111.0 (2)
C9—C8—C7	118.93 (16)	C24—C23—H23A	109.4
C17—C8—C7	121.44 (16)	C22—C23—H23A	109.4
C8—C9—C10	122.27 (19)	C24—C23—H23B	109.4
C8—C9—H9	118.9	C22—C23—H23B	109.4
C10—C9—H9	118.9	H23A—C23—H23B	108.0
C11—C10—C9	119.54 (19)	C25—C24—C23	110.7 (2)
C11—C10—H10	120.2	C25—C24—H24A	109.5
C9—C10—H10	120.2	C23—C24—H24A	109.5
C10—C11—C12	121.43 (18)	C25—C24—H24B	109.5
C10—C11—H11	119.3	C23—C24—H24B	109.5
C12—C11—H11	119.3	H24A—C24—H24B	108.1
C11—C12—C13	120.97 (19)	C24—C25—C26	114.05 (19)
C11—C12—C17	119.64 (18)	C24—C25—H25A	108.7
C13—C12—C17	119.39 (19)	C26—C25—H25A	108.7
C14—C13—C12	120.5 (2)	C24—C25—H25B	108.7
C14—C13—H13	119.8	C26—C25—H25B	108.7
C12—C13—H13	119.8	H25A—C25—H25B	107.6
C13—C14—C15	120.4 (2)	C27—C26—C21	119.38 (17)
C13—C14—H14	119.8	C27—C26—C25	119.43 (18)
C15—C14—H14	119.8	C21—C26—C25	121.17 (18)
C16—C15—C14	120.9 (2)	C28—C27—C26	121.45 (17)
C16—C15—H15	119.5	C28—C27—H27	119.3
C14—C15—H15	119.5	C26—C27—H27	119.3
C15—C16—C17	120.87 (18)	C27—C28—C19	119.86 (17)
C15—C16—H16	119.6	C27—C28—H28	120.1
C17—C16—H16	119.6	C19—C28—H28	120.1

C6—C1—C2—C3	0.6 (3)	C11—C12—C17—C8	−1.8 (2)
C7—C1—C2—C3	−171.82 (16)	C13—C12—C17—C8	177.47 (17)
C6—C1—C2—C18	−172.24 (16)	C9—C8—C17—C16	−176.47 (17)
C7—C1—C2—C18	15.3 (3)	C7—C8—C17—C16	10.7 (3)
C1—C2—C3—C4	−0.2 (3)	C9—C8—C17—C12	2.8 (2)
C18—C2—C3—C4	172.73 (17)	C7—C8—C17—C12	−170.07 (16)
C2—C3—C4—C5	−0.3 (3)	C3—C2—C18—O2	−116.9 (2)
C3—C4—C5—C6	0.3 (3)	C1—C2—C18—O2	55.9 (2)
C4—C5—C6—C1	0.2 (3)	C3—C2—C18—C19	61.0 (2)
C2—C1—C6—C5	−0.7 (3)	C1—C2—C18—C19	−126.17 (18)
C7—C1—C6—C5	171.59 (18)	O2—C18—C19—C28	−174.79 (18)
C6—C1—C7—O1	−135.5 (2)	C2—C18—C19—C28	7.4 (2)
C2—C1—C7—O1	36.8 (3)	O2—C18—C19—C20	4.2 (3)
C6—C1—C7—C8	45.7 (3)	C2—C18—C19—C20	−173.60 (16)
C2—C1—C7—C8	−142.05 (17)	C28—C19—C20—C21	−0.3 (3)
O1—C7—C8—C9	−150.0 (2)	C18—C19—C20—C21	−179.40 (16)
C1—C7—C8—C9	28.8 (3)	C19—C20—C21—C26	−0.8 (3)
O1—C7—C8—C17	22.9 (3)	C19—C20—C21—C22	179.53 (18)
C1—C7—C8—C17	−158.31 (16)	C20—C21—C22—C23	162.3 (2)
C17—C8—C9—C10	−1.2 (3)	C26—C21—C22—C23	−17.3 (3)
C7—C8—C9—C10	171.80 (18)	C21—C22—C23—C24	46.4 (3)
C8—C9—C10—C11	−1.4 (3)	C22—C23—C24—C25	−61.6 (3)
C9—C10—C11—C12	2.5 (3)	C23—C24—C25—C26	46.2 (3)
C10—C11—C12—C13	179.9 (2)	C20—C21—C26—C27	1.2 (3)
C10—C11—C12—C17	−0.8 (3)	C22—C21—C26—C27	−179.15 (19)
C11—C12—C13—C14	−178.9 (2)	C20—C21—C26—C25	−177.22 (18)
C17—C12—C13—C14	1.9 (3)	C22—C21—C26—C25	2.4 (3)
C12—C13—C14—C15	0.4 (3)	C24—C25—C26—C27	164.4 (2)
C13—C14—C15—C16	−1.3 (3)	C24—C25—C26—C21	−17.2 (3)
C14—C15—C16—C17	−0.2 (3)	C21—C26—C27—C28	−0.5 (3)
C15—C16—C17—C12	2.4 (3)	C25—C26—C27—C28	177.99 (18)
C15—C16—C17—C8	−178.34 (18)	C26—C27—C28—C19	−0.7 (3)
C11—C12—C17—C16	177.50 (17)	C20—C19—C28—C27	1.1 (3)
C13—C12—C17—C16	−3.2 (2)	C18—C19—C28—C27	−179.88 (16)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1	0.93	2.29	2.856 (2)	118
C4—H4···Cg3ⁱ	0.93	2.54	3.419 (1)	159
C25—H25A···Cg3ⁱⁱ	0.97	2.94	3.849 (5)	157

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂O₂
M_r	390.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	10.5625 (5), 13.6374 (8), 14.4927 (8)
V (Å³)	2087.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	13047, 4998, 3511
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.100, 1.03
No. of reflections	4998
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1	0.93	2.29	2.856 (2)	118.4
C4—H4···Cg3ⁱ	0.93	2.54	3.419 (1)	159.0
C25—H25A···Cg3ⁱⁱ	0.97	2.94	3.849 (5)	157.0

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

References

Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847–1852. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o26. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1. Google Scholar

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Volume 69| Part 8| August 2013| Page o1201

doi:10.1107/S1600536813018035

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Naphthalen-1-yl){2-[(5,6,7,8-tetra­hydronaphthalen-2-yl)carbonyl]phenyl}methanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone