[2-(2-Meth-oxy-1-naphtho-yl)phen-yl](1-naphth-yl)methanone.

The title compound, C(29)H(20)O(3), adopts an 'S' conformation with a dihedral angle of 68.5 (2)° beween the two acetone planes. The central phenyl ring forms dihedral angles of 83.8 (4) and 84.5 (4)° with the naphthalene and meth-oxy-substituted naphthalene mean planes, respectively. Both carbonyl-group O atoms deviate significantly from the naphthalene moiety and the meth-oxy-substituted naphthalene moiety [0.574 (1) and -1.053 (1) Å, respectively]. The crystal packing is stabilized by C-H⋯O inter-molecular inter-actions, generating C(7) chain and R(2) (2)(10) graph-set motifs.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶). For related structures, see: Tsumuki et al. (2011 ▶); Jagadeesan et al. (2011 ▶); Judas et al. (1995 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C29H20O3

M = 416.45

Monoclinic,

a = 8.3950 (3) Å

b = 8.9983 (4) Å

c = 28.5375 (11) Å

β = 97.188 (2)°

V = 2138.80 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

26364 measured reflections

6299 independent reflections

3875 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.137

S = 1.00

6270 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042747/bt5676sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042747/bt5676Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042747/bt5676Isup3.cml

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

C29H20O3	F(000) = 872
Mr = 416.45	Dx = 1.293 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3875 reflections
a = 8.3950 (3) Å	θ = 1.4–30.1°
b = 8.9983 (4) Å	µ = 0.08 mm−1
c = 28.5375 (11) Å	T = 293 K
β = 97.188 (2)°	Block, colourless
V = 2138.80 (15) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3875 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 30.1°, θmin = 1.4°
ω scans	h = −10→11
26364 measured reflections	k = −12→12
6299 independent reflections	l = −40→40

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.4431P] where P = (Fo2 + 2Fc2)/3
6270 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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	0.15231 (17)	0.63183 (17)	0.06709 (6)	0.0491 (4)
H1	0.2003	0.7251	0.0696	0.059*
C2	−0.01600 (18)	0.6217 (2)	0.06134 (7)	0.0585 (4)
H2	−0.0780	0.7075	0.0606	0.070*
C3	−0.08746 (17)	0.4876 (2)	0.05692 (6)	0.0523 (4)
H3	−0.1989	0.4816	0.0521	0.063*
C4	0.00426 (16)	0.35663 (17)	0.05949 (5)	0.0437 (3)
C5	−0.0706 (2)	0.2162 (2)	0.05524 (7)	0.0606 (5)
H5	−0.1820	0.2108	0.0499	0.073*
C6	0.0158 (2)	0.0898 (2)	0.05872 (8)	0.0763 (6)
H6	−0.0359	−0.0016	0.0553	0.092*
C7	0.1836 (2)	0.0961 (2)	0.06743 (8)	0.0708 (5)
H7	0.2426	0.0084	0.0707	0.085*
C8	0.26131 (18)	0.22922 (17)	0.07110 (6)	0.0507 (4)
H8	0.3728	0.2313	0.0768	0.061*
C9	0.17494 (15)	0.36407 (15)	0.06640 (5)	0.0367 (3)
C10	0.24751 (14)	0.50808 (15)	0.06903 (5)	0.0356 (3)
C11	0.42381 (15)	0.52955 (15)	0.07111 (5)	0.0360 (3)
C12	0.49178 (14)	0.68277 (14)	0.08141 (5)	0.0335 (3)
C13	0.54639 (16)	0.75872 (17)	0.04437 (5)	0.0430 (3)
H13	0.5386	0.7151	0.0146	0.052*
C14	0.61245 (17)	0.89905 (18)	0.05125 (5)	0.0476 (4)
H14	0.6483	0.9495	0.0261	0.057*
C15	0.62522 (18)	0.96406 (17)	0.09500 (6)	0.0509 (4)
H15	0.6696	1.0585	0.0995	0.061*
C16	0.57230 (17)	0.88951 (16)	0.13223 (5)	0.0458 (3)
H16	0.5815	0.9340	0.1619	0.055*
C17	0.50522 (14)	0.74850 (14)	0.12605 (5)	0.0351 (3)
C18	0.45546 (15)	0.66581 (15)	0.16664 (5)	0.0383 (3)
C19	0.44871 (19)	0.74572 (17)	0.21243 (5)	0.0473 (4)
C20	0.5827 (2)	0.74335 (17)	0.24785 (5)	0.0514 (4)
C21	0.7276 (2)	0.67257 (19)	0.24152 (6)	0.0592 (4)
H21	0.7352	0.6202	0.2138	0.071*
C22	0.8574 (3)	0.6795 (2)	0.27548 (7)	0.0767 (6)
H22	0.9527	0.6329	0.2706	0.092*
C23	0.8476 (4)	0.7560 (3)	0.31743 (8)	0.0913 (8)
H23	0.9369	0.7610	0.3402	0.110*
C24	0.7105 (4)	0.8225 (2)	0.32528 (7)	0.0904 (8)
H24	0.7059	0.8718	0.3537	0.108*
C25	0.5721 (3)	0.8193 (2)	0.29106 (6)	0.0696 (5)
C26	0.4270 (4)	0.8903 (3)	0.29698 (8)	0.0916 (8)
H26	0.4179	0.9379	0.3255	0.110*
C27	0.3004 (3)	0.8919 (3)	0.26284 (9)	0.0871 (7)
H27	0.2061	0.9403	0.2679	0.104*
C28	0.3114 (2)	0.8202 (2)	0.21948 (7)	0.0639 (5)
C29	0.0565 (3)	0.9120 (4)	0.18389 (11)	0.1213 (11)
H29A	0.0035	0.8871	0.2108	0.182*
H29B	−0.0166	0.8989	0.1555	0.182*
H29C	0.0913	1.0137	0.1863	0.182*
O1	0.51456 (11)	0.43299 (12)	0.06066 (4)	0.0542 (3)
O2	0.42381 (13)	0.53442 (11)	0.16317 (4)	0.0503 (3)
O3	0.19135 (16)	0.81810 (18)	0.18259 (6)	0.0838 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0369 (7)	0.0401 (8)	0.0693 (11)	−0.0038 (6)	0.0026 (7)	−0.0014 (7)
C2	0.0351 (7)	0.0559 (10)	0.0836 (13)	0.0070 (7)	0.0041 (7)	0.0041 (9)
C3	0.0290 (6)	0.0676 (11)	0.0598 (10)	−0.0062 (7)	0.0033 (6)	0.0063 (8)
C4	0.0375 (7)	0.0522 (9)	0.0420 (8)	−0.0141 (6)	0.0069 (6)	0.0021 (7)
C5	0.0463 (8)	0.0634 (11)	0.0731 (12)	−0.0245 (8)	0.0110 (8)	0.0027 (9)
C6	0.0722 (12)	0.0518 (11)	0.1073 (17)	−0.0308 (10)	0.0205 (11)	−0.0035 (11)
C7	0.0673 (11)	0.0412 (9)	0.1065 (16)	−0.0086 (8)	0.0215 (10)	0.0029 (10)
C8	0.0452 (8)	0.0419 (8)	0.0661 (11)	−0.0069 (6)	0.0115 (7)	0.0009 (7)
C9	0.0355 (6)	0.0399 (7)	0.0349 (7)	−0.0074 (5)	0.0058 (5)	−0.0014 (6)
C10	0.0304 (6)	0.0382 (7)	0.0378 (7)	−0.0053 (5)	0.0025 (5)	−0.0038 (6)
C11	0.0329 (6)	0.0389 (7)	0.0368 (7)	−0.0056 (5)	0.0064 (5)	−0.0080 (6)
C12	0.0274 (5)	0.0355 (7)	0.0384 (7)	−0.0051 (5)	0.0066 (5)	−0.0052 (6)
C13	0.0413 (7)	0.0510 (9)	0.0375 (7)	−0.0073 (6)	0.0087 (6)	−0.0048 (6)
C14	0.0480 (8)	0.0503 (9)	0.0466 (9)	−0.0121 (7)	0.0137 (6)	0.0055 (7)
C15	0.0554 (9)	0.0406 (8)	0.0590 (10)	−0.0179 (7)	0.0154 (7)	−0.0045 (7)
C16	0.0531 (8)	0.0402 (8)	0.0456 (8)	−0.0131 (6)	0.0121 (6)	−0.0104 (6)
C17	0.0345 (6)	0.0339 (7)	0.0379 (7)	−0.0054 (5)	0.0089 (5)	−0.0053 (5)
C18	0.0382 (7)	0.0380 (7)	0.0399 (7)	−0.0026 (5)	0.0098 (6)	−0.0026 (6)
C19	0.0647 (9)	0.0411 (8)	0.0397 (8)	−0.0047 (7)	0.0207 (7)	−0.0036 (6)
C20	0.0812 (11)	0.0394 (8)	0.0356 (8)	−0.0111 (8)	0.0146 (7)	−0.0007 (6)
C21	0.0761 (11)	0.0516 (10)	0.0475 (10)	−0.0066 (9)	−0.0009 (8)	0.0005 (8)
C22	0.0938 (14)	0.0626 (12)	0.0669 (13)	−0.0111 (11)	−0.0165 (11)	0.0125 (10)
C23	0.142 (2)	0.0629 (13)	0.0579 (13)	−0.0311 (14)	−0.0316 (14)	0.0148 (11)
C24	0.173 (3)	0.0596 (13)	0.0351 (10)	−0.0294 (15)	−0.0001 (13)	−0.0008 (9)
C25	0.1247 (17)	0.0506 (10)	0.0361 (9)	−0.0165 (11)	0.0207 (10)	−0.0034 (7)
C26	0.156 (2)	0.0736 (14)	0.0544 (12)	−0.0021 (15)	0.0489 (15)	−0.0182 (11)
C27	0.1146 (18)	0.0784 (15)	0.0797 (16)	0.0114 (13)	0.0576 (14)	−0.0141 (12)
C28	0.0750 (11)	0.0614 (11)	0.0618 (11)	0.0034 (9)	0.0339 (10)	−0.0052 (9)
C29	0.0917 (17)	0.142 (3)	0.139 (3)	0.0545 (17)	0.0487 (16)	0.023 (2)
O1	0.0376 (5)	0.0475 (6)	0.0803 (8)	−0.0058 (4)	0.0181 (5)	−0.0230 (6)
O2	0.0664 (7)	0.0387 (6)	0.0471 (6)	−0.0084 (5)	0.0125 (5)	0.0002 (5)
O3	0.0645 (8)	0.0969 (11)	0.0935 (11)	0.0205 (8)	0.0227 (8)	−0.0104 (9)

C1—C10	1.3678 (19)	C15—H15	0.9300
C1—C2	1.405 (2)	C16—C17	1.3904 (18)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.347 (2)	C17—C18	1.4804 (19)
C2—H2	0.9300	C18—O2	1.2131 (16)
C3—C4	1.405 (2)	C18—C19	1.499 (2)
C3—H3	0.9300	C19—C28	1.370 (2)
C4—C5	1.410 (2)	C19—C20	1.415 (2)
C4—C9	1.4233 (18)	C20—C21	1.404 (2)
C5—C6	1.345 (3)	C20—C25	1.422 (2)
C5—H5	0.9300	C21—C22	1.366 (3)
C6—C7	1.401 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.392 (3)
C7—C8	1.362 (2)	C22—H22	0.9300
C7—H7	0.9300	C23—C24	1.340 (4)
C8—C9	1.411 (2)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.421 (3)
C9—C10	1.4298 (18)	C24—H24	0.9300
C10—C11	1.4864 (17)	C25—C26	1.404 (3)
C11—O1	1.2170 (16)	C26—C27	1.349 (4)
C11—C12	1.5069 (18)	C26—H26	0.9300
C12—C13	1.3842 (19)	C27—C28	1.409 (3)
C12—C17	1.3961 (18)	C27—H27	0.9300
C13—C14	1.383 (2)	C28—O3	1.364 (2)
C13—H13	0.9300	C29—O3	1.417 (3)
C14—C15	1.371 (2)	C29—H29A	0.9600
C14—H14	0.9300	C29—H29B	0.9600
C15—C16	1.376 (2)	C29—H29C	0.9600
C10—C1—C2	121.74 (14)	C15—C16—H16	119.6
C10—C1—H1	119.1	C17—C16—H16	119.6
C2—C1—H1	119.1	C16—C17—C12	119.18 (12)
C3—C2—C1	119.91 (15)	C16—C17—C18	120.59 (12)
C3—C2—H2	120.0	C12—C17—C18	120.18 (11)
C1—C2—H2	120.0	O2—C18—C17	120.42 (12)
C2—C3—C4	120.81 (13)	O2—C18—C19	120.46 (13)
C2—C3—H3	119.6	C17—C18—C19	119.10 (12)
C4—C3—H3	119.6	C28—C19—C20	120.71 (15)
C3—C4—C5	120.80 (13)	C28—C19—C18	119.15 (15)
C3—C4—C9	120.24 (13)	C20—C19—C18	120.14 (13)
C5—C4—C9	118.96 (14)	C21—C20—C19	122.59 (14)
C6—C5—C4	121.39 (15)	C21—C20—C25	118.58 (17)
C6—C5—H5	119.3	C19—C20—C25	118.81 (17)
C4—C5—H5	119.3	C22—C21—C20	120.98 (18)
C5—C6—C7	119.99 (16)	C22—C21—H21	119.5
C5—C6—H6	120.0	C20—C21—H21	119.5
C7—C6—H6	120.0	C21—C22—C23	120.3 (2)
C8—C7—C6	120.71 (17)	C21—C22—H22	119.8
C8—C7—H7	119.6	C23—C22—H22	119.8
C6—C7—H7	119.6	C24—C23—C22	120.6 (2)
C7—C8—C9	120.89 (15)	C24—C23—H23	119.7
C7—C8—H8	119.6	C22—C23—H23	119.7
C9—C8—H8	119.6	C23—C24—C25	121.4 (2)
C8—C9—C4	117.97 (12)	C23—C24—H24	119.3
C8—C9—C10	124.32 (12)	C25—C24—H24	119.3
C4—C9—C10	117.70 (12)	C26—C25—C20	118.2 (2)
C1—C10—C9	119.52 (11)	C26—C25—C24	123.7 (2)
C1—C10—C11	118.01 (12)	C20—C25—C24	118.1 (2)
C9—C10—C11	122.38 (12)	C27—C26—C25	122.34 (18)
O1—C11—C10	123.24 (12)	C27—C26—H26	118.8
O1—C11—C12	117.88 (11)	C25—C26—H26	118.8
C10—C11—C12	118.53 (11)	C26—C27—C28	119.8 (2)
C13—C12—C17	119.41 (12)	C26—C27—H27	120.1
C13—C12—C11	117.14 (12)	C28—C27—H27	120.1
C17—C12—C11	123.43 (11)	O3—C28—C19	115.73 (15)
C14—C13—C12	120.49 (13)	O3—C28—C27	124.13 (18)
C14—C13—H13	119.8	C19—C28—C27	120.1 (2)
C12—C13—H13	119.8	O3—C29—H29A	109.5
C15—C14—C13	120.21 (14)	O3—C29—H29B	109.5
C15—C14—H14	119.9	H29A—C29—H29B	109.5
C13—C14—H14	119.9	O3—C29—H29C	109.5
C14—C15—C16	119.94 (14)	H29A—C29—H29C	109.5
C14—C15—H15	120.0	H29B—C29—H29C	109.5
C16—C15—H15	120.0	C28—O3—C29	119.16 (19)
C15—C16—C17	120.77 (14)
C10—C1—C2—C3	−0.9 (3)	C11—C12—C17—C16	178.86 (12)
C1—C2—C3—C4	2.1 (3)	C13—C12—C17—C18	−176.75 (12)
C2—C3—C4—C5	179.49 (17)	C11—C12—C17—C18	1.67 (19)
C2—C3—C4—C9	−0.6 (2)	C16—C17—C18—O2	−166.95 (14)
C3—C4—C5—C6	−178.45 (18)	C12—C17—C18—O2	10.20 (19)
C9—C4—C5—C6	1.6 (3)	C16—C17—C18—C19	11.53 (19)
C4—C5—C6—C7	0.9 (3)	C12—C17—C18—C19	−171.32 (12)
C5—C6—C7—C8	−1.9 (3)	O2—C18—C19—C28	−94.73 (19)
C6—C7—C8—C9	0.2 (3)	C17—C18—C19—C28	86.79 (18)
C7—C8—C9—C4	2.3 (2)	O2—C18—C19—C20	85.03 (18)
C7—C8—C9—C10	−178.96 (16)	C17—C18—C19—C20	−93.45 (17)
C3—C4—C9—C8	176.89 (14)	C28—C19—C20—C21	−177.85 (16)
C5—C4—C9—C8	−3.2 (2)	C18—C19—C20—C21	2.4 (2)
C3—C4—C9—C10	−1.9 (2)	C28—C19—C20—C25	0.2 (2)
C5—C4—C9—C10	177.98 (14)	C18—C19—C20—C25	−179.52 (14)
C2—C1—C10—C9	−1.7 (2)	C19—C20—C21—C22	176.34 (16)
C2—C1—C10—C11	174.95 (15)	C25—C20—C21—C22	−1.7 (2)
C8—C9—C10—C1	−175.73 (15)	C20—C21—C22—C23	0.7 (3)
C4—C9—C10—C1	3.0 (2)	C21—C22—C23—C24	0.7 (3)
C8—C9—C10—C11	7.8 (2)	C22—C23—C24—C25	−1.0 (3)
C4—C9—C10—C11	−173.44 (12)	C21—C20—C25—C26	179.73 (17)
C1—C10—C11—O1	−160.14 (15)	C19—C20—C25—C26	1.6 (2)
C9—C10—C11—O1	16.4 (2)	C21—C20—C25—C24	1.4 (2)
C1—C10—C11—C12	12.87 (19)	C19—C20—C25—C24	−176.73 (16)
C9—C10—C11—C12	−170.62 (12)	C23—C24—C25—C26	−178.3 (2)
O1—C11—C12—C13	65.58 (17)	C23—C24—C25—C20	−0.1 (3)
C10—C11—C12—C13	−107.81 (14)	C20—C25—C26—C27	−1.8 (3)
O1—C11—C12—C17	−112.87 (15)	C24—C25—C26—C27	176.4 (2)
C10—C11—C12—C17	73.74 (17)	C25—C26—C27—C28	0.2 (4)
C17—C12—C13—C14	−0.6 (2)	C20—C19—C28—O3	178.49 (15)
C11—C12—C13—C14	−179.09 (12)	C18—C19—C28—O3	−1.7 (2)
C12—C13—C14—C15	0.3 (2)	C20—C19—C28—C27	−1.9 (3)
C13—C14—C15—C16	0.1 (2)	C18—C19—C28—C27	177.88 (16)
C14—C15—C16—C17	−0.2 (2)	C26—C27—C28—O3	−178.7 (2)
C15—C16—C17—C12	−0.1 (2)	C26—C27—C28—C19	1.7 (3)
C15—C16—C17—C18	177.11 (14)	C19—C28—O3—C29	−169.66 (19)
C13—C12—C17—C16	0.44 (19)	C27—C28—O3—C29	10.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.49	3.392 (2)	164
C13—H13···O1ii	0.93	2.52	3.440 (2)	170
C27—H27···O2iii	0.93	2.51	3.262 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.49	3.392 (2)	164
C13—H13⋯O1ii	0.93	2.52	3.440 (2)	170
C27—H27⋯O2iii	0.93	2.51	3.262 (3)	138

Symmetry codes: (i) ; (ii) ; (iii) .