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

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 tetra-hydro-pyran ring exhibiting a half-chair conformation. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O inter-action, 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 = 390.46

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.100

S = 1.03

4998 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018035/bg2509sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018035/bg2509Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H22O2	F(000) = 824
Mr = 390.46	Dx = 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

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

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(Fo2) + (0.0423P)2 + 0.1006P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4998 reflections	Δρmax = 0.14 e Å−3
272 parameters	Δρmin = −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)

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .