(8-Benzoyl-2,7-dieth-oxy-naphthalen-1-yl)(phen-yl)methanone.

In the title compound, C28H24O4, the benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, and the benzene rings make a dihedral angle of 20.03 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 68.42 (5) and 71.69 (5)°. In the crystal, adjacent mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Nakaema et al. (2008 ▶); Nishijima et al. (2010 ▶); Sasagawa et al. (2011 ▶); Tsumuki et al. (2011 ▶); Muto et al. (2012 ▶).

Experimental

Crystal data

C28H24O4

M = 424.47

Monoclinic,

a = 7.92185 (14) Å

b = 20.6794 (4) Å

c = 14.2130 (3) Å

β = 106.043 (1)°

V = 2237.68 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 193 K

0.60 × 0.50 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.689, T max = 0.936

39782 measured reflections

4076 independent reflections

3736 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.05

4076 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: IL MILIONE (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049963/su2538sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049963/su2538Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049963/su2538Isup3.cml

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

C28H24O4	F(000) = 896
Mr = 424.47	Dx = 1.260 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 37233 reflections
a = 7.92185 (14) Å	θ = 3.2–68.3°
b = 20.6794 (4) Å	µ = 0.67 mm−1
c = 14.2130 (3) Å	T = 193 K
β = 106.043 (1)°	Needle, colourless
V = 2237.68 (7) Å3	0.60 × 0.50 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4076 independent reflections
Radiation source: fine-focus sealed tube	3736 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.9°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −24→24
Tmin = 0.689, Tmax = 0.936	l = −17→17
39782 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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.5163P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4076 reflections	Δρmax = 0.23 e Å−3
292 parameters	Δρmin = −0.16 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: 0.0075 (3)

Experimental. Spectroscopic data for the title compound: 1H NMR δ (300 MHz, CDCl3); 0.91 (6H, t, J = 6.9 Hz), 3.95 (4H, q, J = 6.9 Hz), 7.16 (2H, d, J = 9.0 Hz), 7.35 (4H, t, J = 7.2 Hz), 7.49(2H, t, J = 7.2 Hz), 7.73 (4H, d, J = 7.2 Hz), 7.91 (2H, d, J = 9.0 Hz) p.p.m.; 13C NMR δ (75 MHz, CDCl3); 13.92, 64.42, 111.89, 121.27, 125.05, 127.43, 128.54, 129.80, 131.79, 131.95, 138.93, 155.52, 197.04 p.p.m.; IR (KBr, cm-1): 1665 (C═ O), 1612, 1510, 1452 (Ar), 1266 (═C—O—C).

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
O1	0.29349 (11)	0.08669 (4)	1.04839 (6)	0.0381 (2)
O2	−0.21634 (12)	0.01858 (4)	0.55669 (6)	0.0458 (2)
O3	−0.02728 (10)	0.16304 (4)	0.86895 (6)	0.0383 (2)
O4	0.08625 (10)	0.12983 (4)	0.66958 (6)	0.0414 (2)
C1	0.12835 (13)	0.06508 (5)	0.88895 (8)	0.0299 (2)
C2	0.21642 (14)	0.04134 (5)	0.98017 (8)	0.0325 (3)
C3	0.21668 (15)	−0.02515 (6)	1.00229 (9)	0.0367 (3)
H3	0.2781	−0.0406	1.0654	0.044*
C4	0.12768 (15)	−0.06697 (6)	0.93199 (9)	0.0375 (3)
H4	0.1268	−0.1117	0.9471	0.045*
C5	−0.05370 (16)	−0.08988 (6)	0.76527 (10)	0.0398 (3)
H5	−0.0536	−0.1344	0.7817	0.048*
C6	−0.14091 (16)	−0.07056 (6)	0.67303 (9)	0.0410 (3)
H6	−0.2012	−0.1012	0.6258	0.049*
C7	−0.14038 (15)	−0.00448 (6)	0.64861 (9)	0.0361 (3)
C8	−0.05794 (14)	0.04132 (5)	0.71690 (8)	0.0314 (2)
C9	0.03474 (13)	0.02192 (5)	0.81381 (8)	0.0302 (2)
C10	0.03651 (14)	−0.04555 (5)	0.83711 (9)	0.0341 (3)
C11	0.11515 (14)	0.13756 (5)	0.87770 (8)	0.0299 (2)
C12	0.27340 (14)	0.17695 (5)	0.87977 (8)	0.0320 (2)
C13	0.43562 (15)	0.14857 (6)	0.88777 (9)	0.0390 (3)
H13	0.4468	0.1028	0.8910	0.047*
C14	0.58108 (16)	0.18650 (7)	0.89110 (10)	0.0477 (3)
H14	0.6918	0.1668	0.8966	0.057*
C15	0.56497 (18)	0.25260 (7)	0.88645 (11)	0.0542 (4)
H15	0.6650	0.2787	0.8893	0.065*
C16	0.4039 (2)	0.28145 (7)	0.87758 (13)	0.0586 (4)
H16	0.3933	0.3272	0.8739	0.070*
C17	0.25816 (17)	0.24361 (6)	0.87402 (11)	0.0455 (3)
H17	0.1474	0.2634	0.8676	0.055*
C18	−0.05219 (14)	0.10942 (5)	0.67903 (8)	0.0310 (2)
C19	−0.21431 (14)	0.14952 (5)	0.65338 (8)	0.0310 (2)
C20	−0.37066 (15)	0.12789 (6)	0.66818 (9)	0.0390 (3)
H20	−0.3762	0.0860	0.6947	0.047*
C21	−0.51890 (16)	0.16678 (7)	0.64465 (10)	0.0459 (3)
H21	−0.6257	0.1516	0.6547	0.055*
C22	−0.51078 (18)	0.22760 (7)	0.60655 (10)	0.0483 (3)
H22	−0.6126	0.2541	0.5898	0.058*
C23	−0.35529 (19)	0.25015 (7)	0.59266 (11)	0.0531 (4)
H23	−0.3498	0.2924	0.5673	0.064*
C24	−0.20769 (17)	0.21117 (6)	0.61576 (10)	0.0435 (3)
H24	−0.1010	0.2267	0.6058	0.052*
C25	0.42914 (16)	0.06661 (6)	1.13328 (9)	0.0420 (3)
H25A	0.5139	0.0379	1.1140	0.050*
H25B	0.3777	0.0429	1.1792	0.050*
C26	0.5191 (2)	0.12683 (7)	1.18056 (11)	0.0571 (4)
H26A	0.4357	0.1534	1.2032	0.068*
H26B	0.5624	0.1513	1.1329	0.068*
H26C	0.6181	0.1151	1.2365	0.068*
C27	−0.26626 (18)	−0.02602 (7)	0.47696 (9)	0.0469 (3)
H27A	−0.3661	−0.0530	0.4830	0.056*
H27B	−0.1667	−0.0549	0.4766	0.056*
C28	−0.31808 (19)	0.01303 (7)	0.38490 (10)	0.0515 (3)
H28A	−0.2205	0.0413	0.3817	0.062*
H28B	−0.4211	0.0394	0.3844	0.062*
H28C	−0.3465	−0.0160	0.3282	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0391 (4)	0.0380 (4)	0.0334 (4)	0.0027 (3)	0.0035 (3)	0.0007 (3)
O2	0.0568 (6)	0.0368 (5)	0.0362 (5)	0.0032 (4)	−0.0001 (4)	−0.0053 (4)
O3	0.0266 (4)	0.0375 (4)	0.0499 (5)	0.0040 (3)	0.0094 (4)	−0.0037 (4)
O4	0.0306 (4)	0.0456 (5)	0.0502 (5)	−0.0024 (3)	0.0149 (4)	0.0054 (4)
C1	0.0243 (5)	0.0317 (6)	0.0356 (6)	0.0007 (4)	0.0114 (4)	0.0011 (4)
C2	0.0275 (5)	0.0355 (6)	0.0355 (6)	0.0016 (4)	0.0105 (5)	−0.0005 (5)
C3	0.0343 (6)	0.0389 (6)	0.0372 (6)	0.0056 (5)	0.0103 (5)	0.0077 (5)
C4	0.0375 (6)	0.0304 (6)	0.0463 (7)	0.0036 (5)	0.0146 (5)	0.0069 (5)
C5	0.0424 (7)	0.0278 (6)	0.0502 (7)	0.0005 (5)	0.0146 (6)	−0.0009 (5)
C6	0.0421 (7)	0.0326 (6)	0.0463 (7)	−0.0014 (5)	0.0090 (6)	−0.0082 (5)
C7	0.0335 (6)	0.0362 (6)	0.0376 (6)	0.0029 (5)	0.0081 (5)	−0.0026 (5)
C8	0.0271 (5)	0.0310 (6)	0.0371 (6)	0.0027 (4)	0.0104 (5)	−0.0006 (5)
C9	0.0252 (5)	0.0309 (5)	0.0366 (6)	0.0017 (4)	0.0120 (4)	0.0006 (4)
C10	0.0314 (6)	0.0305 (6)	0.0423 (7)	0.0022 (4)	0.0136 (5)	0.0014 (5)
C11	0.0263 (5)	0.0336 (6)	0.0288 (5)	0.0019 (4)	0.0059 (4)	−0.0014 (4)
C12	0.0286 (6)	0.0341 (6)	0.0316 (6)	−0.0007 (4)	0.0054 (4)	0.0023 (4)
C13	0.0304 (6)	0.0393 (6)	0.0472 (7)	0.0021 (5)	0.0104 (5)	0.0066 (5)
C14	0.0273 (6)	0.0594 (8)	0.0551 (8)	−0.0003 (5)	0.0090 (6)	0.0139 (7)
C15	0.0394 (7)	0.0570 (9)	0.0628 (9)	−0.0168 (6)	0.0085 (6)	0.0119 (7)
C16	0.0539 (8)	0.0367 (7)	0.0840 (11)	−0.0087 (6)	0.0171 (8)	0.0089 (7)
C17	0.0377 (7)	0.0362 (7)	0.0616 (8)	0.0017 (5)	0.0119 (6)	0.0057 (6)
C18	0.0291 (5)	0.0345 (6)	0.0291 (6)	−0.0020 (4)	0.0077 (4)	−0.0019 (4)
C19	0.0307 (6)	0.0317 (6)	0.0295 (6)	−0.0002 (4)	0.0065 (4)	−0.0018 (4)
C20	0.0327 (6)	0.0339 (6)	0.0501 (7)	−0.0020 (5)	0.0110 (5)	−0.0004 (5)
C21	0.0296 (6)	0.0488 (7)	0.0579 (8)	0.0000 (5)	0.0097 (6)	−0.0075 (6)
C22	0.0419 (7)	0.0497 (8)	0.0476 (8)	0.0163 (6)	0.0030 (6)	−0.0005 (6)
C23	0.0581 (8)	0.0433 (7)	0.0585 (9)	0.0130 (6)	0.0173 (7)	0.0170 (6)
C24	0.0419 (7)	0.0410 (7)	0.0498 (8)	0.0018 (5)	0.0162 (6)	0.0098 (6)
C25	0.0373 (6)	0.0481 (7)	0.0360 (6)	0.0040 (5)	0.0026 (5)	0.0033 (5)
C26	0.0538 (8)	0.0551 (9)	0.0504 (8)	−0.0017 (7)	−0.0055 (7)	−0.0013 (7)
C27	0.0516 (8)	0.0469 (7)	0.0394 (7)	−0.0044 (6)	0.0082 (6)	−0.0101 (6)
C28	0.0513 (8)	0.0602 (9)	0.0406 (7)	−0.0046 (6)	0.0091 (6)	−0.0049 (6)

O1—C2	1.3657 (14)	C15—C16	1.382 (2)
O1—C25	1.4374 (14)	C15—H15	0.9500
O2—C7	1.3645 (15)	C16—C17	1.3841 (18)
O2—C27	1.4297 (15)	C16—H16	0.9500
O3—C11	1.2201 (13)	C17—H17	0.9500
O4—C18	1.2167 (13)	C18—C19	1.4870 (15)
C1—C2	1.3815 (16)	C19—C20	1.3865 (16)
C1—C9	1.4315 (15)	C19—C24	1.3890 (17)
C1—C11	1.5079 (15)	C20—C21	1.3858 (17)
C2—C3	1.4104 (16)	C20—H20	0.9500
C3—C4	1.3616 (17)	C21—C22	1.378 (2)
C3—H3	0.9500	C21—H21	0.9500
C4—C10	1.4135 (17)	C22—C23	1.381 (2)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.3620 (18)	C23—C24	1.3830 (18)
C5—C10	1.4108 (17)	C23—H23	0.9500
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.4101 (17)	C25—C26	1.4985 (19)
C6—H6	0.9500	C25—H25A	0.9900
C7—C8	1.3839 (16)	C25—H25B	0.9900
C8—C9	1.4277 (16)	C26—H26A	0.9800
C8—C18	1.5129 (15)	C26—H26B	0.9800
C9—C10	1.4331 (15)	C26—H26C	0.9800
C11—C12	1.4886 (15)	C27—C28	1.4952 (19)
C12—C17	1.3842 (17)	C27—H27A	0.9900
C12—C13	1.3886 (15)	C27—H27B	0.9900
C13—C14	1.3839 (17)	C28—H28A	0.9800
C13—H13	0.9500	C28—H28B	0.9800
C14—C15	1.373 (2)	C28—H28C	0.9800
C14—H14	0.9500
C2—O1—C25	118.78 (9)	C17—C16—H16	120.0
C7—O2—C27	119.05 (10)	C16—C17—C12	120.17 (12)
C2—C1—C9	120.12 (10)	C16—C17—H17	119.9
C2—C1—C11	117.05 (10)	C12—C17—H17	119.9
C9—C1—C11	122.29 (10)	O4—C18—C19	121.56 (10)
O1—C2—C1	115.67 (10)	O4—C18—C8	118.61 (10)
O1—C2—C3	122.57 (10)	C19—C18—C8	119.83 (9)
C1—C2—C3	121.66 (11)	C20—C19—C24	119.00 (11)
C4—C3—C2	119.15 (11)	C20—C19—C18	122.01 (10)
C4—C3—H3	120.4	C24—C19—C18	118.96 (10)
C2—C3—H3	120.4	C21—C20—C19	120.60 (11)
C3—C4—C10	121.70 (11)	C21—C20—H20	119.7
C3—C4—H4	119.1	C19—C20—H20	119.7
C10—C4—H4	119.1	C22—C21—C20	119.74 (12)
C6—C5—C10	121.79 (11)	C22—C21—H21	120.1
C6—C5—H5	119.1	C20—C21—H21	120.1
C10—C5—H5	119.1	C21—C22—C23	120.31 (12)
C5—C6—C7	119.08 (11)	C21—C22—H22	119.8
C5—C6—H6	120.5	C23—C22—H22	119.8
C7—C6—H6	120.5	C22—C23—C24	119.87 (12)
O2—C7—C8	115.47 (10)	C22—C23—H23	120.1
O2—C7—C6	122.95 (11)	C24—C23—H23	120.1
C8—C7—C6	121.56 (11)	C23—C24—C19	120.46 (12)
C7—C8—C9	120.10 (10)	C23—C24—H24	119.8
C7—C8—C18	116.25 (10)	C19—C24—H24	119.8
C9—C8—C18	123.15 (10)	O1—C25—C26	106.80 (10)
C8—C9—C1	124.53 (10)	O1—C25—H25A	110.4
C8—C9—C10	117.78 (10)	C26—C25—H25A	110.4
C1—C9—C10	117.69 (10)	O1—C25—H25B	110.4
C5—C10—C4	120.66 (11)	C26—C25—H25B	110.4
C5—C10—C9	119.65 (11)	H25A—C25—H25B	108.6
C4—C10—C9	119.69 (11)	C25—C26—H26A	109.5
O3—C11—C12	121.04 (10)	C25—C26—H26B	109.5
O3—C11—C1	118.37 (9)	H26A—C26—H26B	109.5
C12—C11—C1	120.57 (9)	C25—C26—H26C	109.5
C17—C12—C13	119.30 (11)	H26A—C26—H26C	109.5
C17—C12—C11	118.99 (10)	H26B—C26—H26C	109.5
C13—C12—C11	121.71 (10)	O2—C27—C28	107.10 (11)
C14—C13—C12	120.42 (12)	O2—C27—H27A	110.3
C14—C13—H13	119.8	C28—C27—H27A	110.3
C12—C13—H13	119.8	O2—C27—H27B	110.3
C15—C14—C13	119.82 (12)	C28—C27—H27B	110.3
C15—C14—H14	120.1	H27A—C27—H27B	108.5
C13—C14—H14	120.1	C27—C28—H28A	109.5
C14—C15—C16	120.36 (12)	C27—C28—H28B	109.5
C14—C15—H15	119.8	H28A—C28—H28B	109.5
C16—C15—H15	119.8	C27—C28—H28C	109.5
C15—C16—C17	119.93 (13)	H28A—C28—H28C	109.5
C15—C16—H16	120.0	H28B—C28—H28C	109.5
C25—O1—C2—C1	−161.30 (10)	C2—C1—C11—O3	−108.29 (12)
C25—O1—C2—C3	22.47 (15)	C9—C1—C11—O3	63.28 (14)
C9—C1—C2—O1	−176.52 (9)	C2—C1—C11—C12	70.21 (13)
C11—C1—C2—O1	−4.75 (14)	C9—C1—C11—C12	−118.21 (11)
C9—C1—C2—C3	−0.25 (16)	O3—C11—C12—C17	1.58 (17)
C11—C1—C2—C3	171.51 (10)	C1—C11—C12—C17	−176.88 (11)
O1—C2—C3—C4	175.92 (10)	O3—C11—C12—C13	−178.72 (11)
C1—C2—C3—C4	−0.08 (16)	C1—C11—C12—C13	2.81 (16)
C2—C3—C4—C10	0.64 (17)	C17—C12—C13—C14	0.74 (19)
C10—C5—C6—C7	0.25 (18)	C11—C12—C13—C14	−178.95 (11)
C27—O2—C7—C8	164.97 (11)	C12—C13—C14—C15	0.0 (2)
C27—O2—C7—C6	−13.53 (17)	C13—C14—C15—C16	−0.6 (2)
C5—C6—C7—O2	176.45 (11)	C14—C15—C16—C17	0.4 (2)
C5—C6—C7—C8	−1.97 (18)	C15—C16—C17—C12	0.3 (2)
O2—C7—C8—C9	−176.28 (9)	C13—C12—C17—C16	−0.9 (2)
C6—C7—C8—C9	2.25 (17)	C11—C12—C17—C16	178.82 (13)
O2—C7—C8—C18	−4.12 (14)	C7—C8—C18—O4	−105.71 (12)
C6—C7—C8—C18	174.41 (10)	C9—C8—C18—O4	66.19 (14)
C7—C8—C9—C1	178.17 (10)	C7—C8—C18—C19	73.69 (13)
C18—C8—C9—C1	6.58 (16)	C9—C8—C18—C19	−114.42 (12)
C7—C8—C9—C10	−0.83 (15)	O4—C18—C19—C20	−176.90 (11)
C18—C8—C9—C10	−172.42 (9)	C8—C18—C19—C20	3.72 (16)
C2—C1—C9—C8	−178.97 (10)	O4—C18—C19—C24	1.44 (17)
C11—C1—C9—C8	9.71 (16)	C8—C18—C19—C24	−177.94 (11)
C2—C1—C9—C10	0.03 (14)	C24—C19—C20—C21	0.84 (18)
C11—C1—C9—C10	−171.29 (9)	C18—C19—C20—C21	179.18 (11)
C6—C5—C10—C4	−179.28 (11)	C19—C20—C21—C22	−0.3 (2)
C6—C5—C10—C9	1.12 (17)	C20—C21—C22—C23	−0.6 (2)
C3—C4—C10—C5	179.54 (11)	C21—C22—C23—C24	0.9 (2)
C3—C4—C10—C9	−0.86 (17)	C22—C23—C24—C19	−0.3 (2)
C8—C9—C10—C5	−0.82 (15)	C20—C19—C24—C23	−0.53 (19)
C1—C9—C10—C5	−179.89 (10)	C18—C19—C24—C23	−178.92 (12)
C8—C9—C10—C4	179.57 (10)	C2—O1—C25—C26	165.89 (11)
C1—C9—C10—C4	0.50 (15)	C7—O2—C27—C28	−171.15 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3i	0.95	2.37	3.2404 (16)	153
C21—H21···O4ii	0.95	2.39	3.3326 (16)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3i	0.95	2.37	3.2404 (16)	153
C21—H21⋯O4ii	0.95	2.39	3.3326 (16)	171

Symmetry codes: (i) ; (ii) .