(2,7-Dimeth-oxy-naphthalen-1-yl)(3-nitro-phen-yl)methanone.

The title compound, C(19)H(15)NO(5), has an intra-molecular C-H⋯O=C hydrogen bond between a naphthalene H atom and the O atom of the carbonyl group. The inter-planar angle between the naphthalene ring system and the benzene ring is 69.59 (5)°. The dihedral angle between the bridging carbonyl C-C(=O)-C plane and the naphthalene ring system is 61.02 (6)°, which is far larger than that between the bridging carbonyl plane and the benzene ring [12.68 (7)°]. The nitro group is slightly out of the plane of the benzene ring [O-N-C-C torsion angle = 4.97 (17)°]. In the crystal, the packing is mainly stabilized by C-H⋯O inter-actions between an H atom of the benzene ring and an O atom of the nitro group.

Related literature

For the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene giving aroylated naphthalene compounds, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Kato et al. (2010 ▶); Mitsui et al. (2008 ▶); Muto et al. (2010 ▶); Nishijima et al. (2010 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C19H15NO5

M = 337.32

Monoclinic,

a = 8.05658 (18) Å

b = 17.0634 (4) Å

c = 11.7660 (3) Å

β = 94.660 (1)°

V = 1612.15 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.85 mm−1

T = 193 K

0.55 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.653, T max = 0.849

29060 measured reflections

2942 independent reflections

2685 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.00

2942 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042819/rn2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042819/rn2073Isup2.hkl

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

C19H15NO5	F(000) = 704
Mr = 337.32	Dx = 1.390 Mg m−3
Monoclinic, P21/n	Melting point = 418.8–419.1 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54187 Å
a = 8.05658 (18) Å	Cell parameters from 23523 reflections
b = 17.0634 (4) Å	θ = 3.8–68.2°
c = 11.7660 (3) Å	µ = 0.85 mm−1
β = 94.660 (1)°	T = 193 K
V = 1612.15 (6) Å3	Block, yellow
Z = 4	0.55 × 0.20 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2942 independent reflections
Radiation source: rotating anode	2685 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.6°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −20→20
Tmin = 0.653, Tmax = 0.849	l = −14→14
29060 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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.4684P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2942 reflections	Δρmax = 0.19 e Å−3
229 parameters	Δρmin = −0.14 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: 0.0073 (4)

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	0.27637 (10)	0.43017 (5)	0.69042 (8)	0.0421 (2)
O2	0.00689 (11)	0.59531 (5)	0.62855 (8)	0.0451 (3)
O3	−0.04611 (11)	0.18744 (5)	0.79381 (8)	0.0432 (2)
O4	0.64787 (14)	0.65633 (7)	1.04665 (10)	0.0638 (3)
O5	0.71205 (11)	0.57358 (6)	0.91928 (9)	0.0526 (3)
N1	0.61035 (14)	0.60860 (6)	0.97139 (10)	0.0416 (3)
C1	−0.00844 (14)	0.46560 (7)	0.68859 (9)	0.0309 (3)
C2	−0.08844 (15)	0.52991 (7)	0.63812 (10)	0.0343 (3)
C3	−0.25834 (16)	0.52651 (8)	0.59896 (10)	0.0377 (3)
H3	−0.3127	0.5713	0.5655	0.045*
C4	−0.34356 (15)	0.45847 (8)	0.60951 (10)	0.0371 (3)
H4	−0.4586	0.4568	0.5843	0.044*
C5	−0.26677 (14)	0.39048 (7)	0.65650 (9)	0.0328 (3)
C6	−0.35374 (15)	0.31846 (8)	0.66192 (10)	0.0372 (3)
H6	−0.4679	0.3161	0.6347	0.045*
C7	−0.27714 (16)	0.25281 (8)	0.70512 (10)	0.0386 (3)
H7	−0.3364	0.2047	0.7061	0.046*
C8	−0.10780 (15)	0.25655 (7)	0.74891 (10)	0.0342 (3)
C9	−0.01892 (14)	0.32474 (7)	0.74566 (9)	0.0318 (3)
H9	0.0942	0.3262	0.7755	0.038*
C10	−0.09579 (14)	0.39342 (7)	0.69773 (9)	0.0298 (3)
C11	0.17233 (14)	0.47124 (7)	0.73012 (9)	0.0307 (3)
C12	0.22134 (14)	0.52681 (7)	0.82550 (9)	0.0298 (3)
C13	0.38964 (14)	0.54220 (7)	0.85296 (10)	0.0311 (3)
H13	0.4725	0.5190	0.8108	0.037*
C14	0.43276 (15)	0.59185 (7)	0.94285 (10)	0.0341 (3)
C15	0.31664 (17)	0.62608 (8)	1.00789 (11)	0.0425 (3)
H15	0.3505	0.6597	1.0699	0.051*
C16	0.15028 (17)	0.61002 (8)	0.98007 (11)	0.0444 (3)
H16	0.0681	0.6327	1.0234	0.053*
C17	0.10273 (15)	0.56103 (8)	0.88928 (10)	0.0368 (3)
H17	−0.0121	0.5507	0.8704	0.044*
C18	−0.05995 (17)	0.65802 (8)	0.55877 (11)	0.0412 (3)
H18A	0.0266	0.6975	0.5507	0.049*
H18B	−0.1535	0.6819	0.5943	0.049*
H18C	−0.0988	0.6377	0.4834	0.049*
C19	0.12202 (18)	0.18734 (8)	0.84244 (12)	0.0461 (3)
H19A	0.1498	0.1354	0.8740	0.055*
H19B	0.1349	0.2266	0.9033	0.055*
H19C	0.1968	0.2000	0.7834	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0304 (5)	0.0488 (5)	0.0476 (5)	0.0002 (4)	0.0063 (4)	−0.0138 (4)
O2	0.0411 (5)	0.0371 (5)	0.0550 (6)	−0.0072 (4)	−0.0099 (4)	0.0087 (4)
O3	0.0441 (5)	0.0346 (5)	0.0504 (5)	−0.0017 (4)	−0.0003 (4)	0.0029 (4)
O4	0.0542 (7)	0.0562 (6)	0.0767 (7)	−0.0120 (5)	−0.0224 (6)	−0.0144 (6)
O5	0.0293 (5)	0.0639 (7)	0.0639 (6)	−0.0023 (4)	−0.0007 (4)	0.0040 (5)
N1	0.0356 (6)	0.0387 (6)	0.0484 (6)	−0.0068 (5)	−0.0087 (5)	0.0058 (5)
C1	0.0280 (6)	0.0360 (6)	0.0287 (5)	−0.0012 (5)	0.0016 (4)	−0.0036 (5)
C2	0.0340 (6)	0.0349 (6)	0.0338 (6)	−0.0023 (5)	0.0002 (5)	−0.0021 (5)
C3	0.0346 (7)	0.0406 (7)	0.0370 (6)	0.0039 (5)	−0.0038 (5)	0.0010 (5)
C4	0.0272 (6)	0.0481 (7)	0.0351 (6)	0.0002 (5)	−0.0023 (5)	−0.0016 (5)
C5	0.0288 (6)	0.0421 (7)	0.0275 (6)	−0.0024 (5)	0.0024 (4)	−0.0034 (5)
C6	0.0287 (6)	0.0476 (7)	0.0350 (6)	−0.0078 (5)	0.0004 (5)	−0.0025 (5)
C7	0.0391 (7)	0.0401 (7)	0.0369 (6)	−0.0109 (5)	0.0048 (5)	−0.0031 (5)
C8	0.0378 (6)	0.0348 (6)	0.0302 (6)	−0.0010 (5)	0.0049 (5)	−0.0021 (5)
C9	0.0277 (6)	0.0387 (6)	0.0289 (5)	0.0000 (5)	0.0019 (4)	−0.0030 (5)
C10	0.0280 (6)	0.0365 (6)	0.0252 (5)	−0.0016 (5)	0.0033 (4)	−0.0039 (4)
C11	0.0280 (6)	0.0334 (6)	0.0310 (6)	−0.0014 (5)	0.0042 (5)	0.0014 (5)
C12	0.0271 (6)	0.0324 (6)	0.0300 (6)	−0.0009 (4)	0.0018 (4)	0.0017 (4)
C13	0.0283 (6)	0.0324 (6)	0.0326 (6)	0.0014 (5)	0.0029 (5)	0.0033 (5)
C14	0.0305 (6)	0.0338 (6)	0.0368 (6)	−0.0036 (5)	−0.0042 (5)	0.0042 (5)
C15	0.0461 (8)	0.0417 (7)	0.0386 (7)	−0.0012 (6)	−0.0023 (6)	−0.0089 (5)
C16	0.0395 (7)	0.0521 (8)	0.0422 (7)	0.0048 (6)	0.0075 (6)	−0.0115 (6)
C17	0.0273 (6)	0.0455 (7)	0.0377 (6)	0.0006 (5)	0.0030 (5)	−0.0034 (5)
C18	0.0481 (8)	0.0356 (6)	0.0396 (7)	0.0013 (6)	0.0021 (6)	0.0020 (5)
C19	0.0496 (8)	0.0389 (7)	0.0482 (8)	0.0051 (6)	−0.0053 (6)	0.0003 (6)

O1—C11	1.2147 (14)	C7—H7	0.9500
O2—C2	1.3646 (15)	C8—C9	1.3685 (17)
O2—C18	1.4273 (15)	C9—C10	1.4206 (17)
O3—C8	1.3689 (15)	C9—H9	0.9500
O3—C19	1.4270 (16)	C11—C12	1.4974 (16)
O4—N1	1.2229 (15)	C12—C17	1.3906 (16)
O5—N1	1.2189 (15)	C12—C13	1.3931 (16)
N1—C14	1.4709 (16)	C13—C14	1.3774 (17)
C1—C2	1.3821 (17)	C13—H13	0.9500
C1—C10	1.4269 (16)	C14—C15	1.3851 (18)
C1—C11	1.5012 (16)	C15—C16	1.3810 (19)
C2—C3	1.4096 (17)	C15—H15	0.9500
C3—C4	1.3596 (18)	C16—C17	1.3858 (18)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.4067 (18)	C17—H17	0.9500
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.4187 (17)	C18—H18B	0.9800
C5—C10	1.4236 (16)	C18—H18C	0.9800
C6—C7	1.3576 (18)	C19—H19A	0.9800
C6—H6	0.9500	C19—H19B	0.9800
C7—C8	1.4201 (18)	C19—H19C	0.9800
C2—O2—C18	118.16 (10)	C5—C10—C1	118.31 (11)
C8—O3—C19	117.31 (10)	O1—C11—C12	120.36 (10)
O5—N1—O4	123.64 (11)	O1—C11—C1	121.29 (10)
O5—N1—C14	118.11 (11)	C12—C11—C1	118.31 (10)
O4—N1—C14	118.25 (12)	C17—C12—C13	119.62 (11)
C2—C1—C10	120.14 (11)	C17—C12—C11	121.29 (10)
C2—C1—C11	119.68 (10)	C13—C12—C11	119.05 (10)
C10—C1—C11	120.15 (10)	C14—C13—C12	118.30 (11)
O2—C2—C1	116.03 (10)	C14—C13—H13	120.9
O2—C2—C3	123.01 (11)	C12—C13—H13	120.9
C1—C2—C3	120.96 (11)	C13—C14—C15	122.96 (11)
C4—C3—C2	119.31 (12)	C13—C14—N1	118.34 (11)
C4—C3—H3	120.3	C15—C14—N1	118.69 (11)
C2—C3—H3	120.3	C16—C15—C14	118.13 (11)
C3—C4—C5	122.06 (11)	C16—C15—H15	120.9
C3—C4—H4	119.0	C14—C15—H15	120.9
C5—C4—H4	119.0	C15—C16—C17	120.31 (12)
C4—C5—C6	121.94 (11)	C15—C16—H16	119.8
C4—C5—C10	119.17 (11)	C17—C16—H16	119.8
C6—C5—C10	118.88 (11)	C16—C17—C12	120.68 (11)
C7—C6—C5	121.36 (11)	C16—C17—H17	119.7
C7—C6—H6	119.3	C12—C17—H17	119.7
C5—C6—H6	119.3	O2—C18—H18A	109.5
C6—C7—C8	119.53 (11)	O2—C18—H18B	109.5
C6—C7—H7	120.2	H18A—C18—H18B	109.5
C8—C7—H7	120.2	O2—C18—H18C	109.5
C9—C8—O3	124.67 (11)	H18A—C18—H18C	109.5
C9—C8—C7	121.17 (11)	H18B—C18—H18C	109.5
O3—C8—C7	114.16 (11)	O3—C19—H19A	109.5
C8—C9—C10	120.02 (11)	O3—C19—H19B	109.5
C8—C9—H9	120.0	H19A—C19—H19B	109.5
C10—C9—H9	120.0	O3—C19—H19C	109.5
C9—C10—C5	119.00 (11)	H19A—C19—H19C	109.5
C9—C10—C1	122.69 (10)	H19B—C19—H19C	109.5
C18—O2—C2—C1	168.50 (11)	C2—C1—C10—C9	178.10 (11)
C18—O2—C2—C3	−11.15 (17)	C11—C1—C10—C9	0.20 (16)
C10—C1—C2—O2	−177.16 (10)	C2—C1—C10—C5	−1.63 (16)
C11—C1—C2—O2	0.74 (16)	C11—C1—C10—C5	−179.53 (10)
C10—C1—C2—C3	2.49 (18)	C2—C1—C11—O1	−117.94 (13)
C11—C1—C2—C3	−179.60 (10)	C10—C1—C11—O1	59.96 (15)
O2—C2—C3—C4	178.56 (11)	C2—C1—C11—C12	64.42 (14)
C1—C2—C3—C4	−1.07 (18)	C10—C1—C11—C12	−117.67 (12)
C2—C3—C4—C5	−1.23 (19)	O1—C11—C12—C17	−165.28 (11)
C3—C4—C5—C6	−176.62 (11)	C1—C11—C12—C17	12.37 (16)
C3—C4—C5—C10	2.03 (18)	O1—C11—C12—C13	12.50 (17)
C4—C5—C6—C7	178.48 (11)	C1—C11—C12—C13	−169.84 (10)
C10—C5—C6—C7	−0.17 (18)	C17—C12—C13—C14	−0.50 (17)
C5—C6—C7—C8	1.83 (18)	C11—C12—C13—C14	−178.32 (10)
C19—O3—C8—C9	1.23 (17)	C12—C13—C14—C15	0.96 (18)
C19—O3—C8—C7	−178.24 (11)	C12—C13—C14—N1	−179.56 (10)
C6—C7—C8—C9	−1.73 (18)	O5—N1—C14—C13	−4.97 (17)
C6—C7—C8—O3	177.76 (11)	O4—N1—C14—C13	175.63 (11)
O3—C8—C9—C10	−179.52 (10)	O5—N1—C14—C15	174.53 (12)
C7—C8—C9—C10	−0.09 (17)	O4—N1—C14—C15	−4.87 (17)
C8—C9—C10—C5	1.75 (16)	C13—C14—C15—C16	−0.7 (2)
C8—C9—C10—C1	−177.99 (10)	N1—C14—C15—C16	179.87 (12)
C4—C5—C10—C9	179.68 (10)	C14—C15—C16—C17	−0.1 (2)
C6—C5—C10—C9	−1.63 (16)	C15—C16—C17—C12	0.5 (2)
C4—C5—C10—C1	−0.57 (16)	C13—C12—C17—C16	−0.24 (19)
C6—C5—C10—C1	178.12 (10)	C11—C12—C17—C16	177.54 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.60	3.3150 (15)	132
C9—H9···O1	0.95	2.56	3.0935 (14)	116
C17—H17···O5i	0.95	2.37	3.2028 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.60	3.3150 (15)	132
C9—H9⋯O1	0.95	2.56	3.0935 (14)	116
C17—H17⋯O5i	0.95	2.37	3.2028 (15)	146

Symmetry code: (i) .