2,7-Dimethoxy--1-(4-nitro-benzo-yl)-naphthalene.

In the title compound, C(19)H(15)NO(5), the dihedral angle between the naphthalene ring system and the benzene ring is 61.97 (5)°. The dihedral between the naphthalene ring system and the bridging carbonyl C-C(=O)-C plane is 54.68 (6)°, far larger than that [12.54 (7)°] between the phenyl group and the bridging carbonyl group. The nitro group and the phenyl ring are almost coplanar [O-N-C-C torsion angle = 2.94 (19)°]. In the crystal, mol-ecules are linked by C-H⋯π inter-actions and the phenyl rings are involved in a centrosymmetric π-π inter-action with a perpendicular distance of 3.523 Å and a lateral offset of 1.497 Å. In addition, weak inter-molecular C-H⋯O hydrogen bonds are formed between an H atom of one meth-oxy group and a nearby carbonyl O atom.

Related literature

For general background to the regioselective formation of peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009 ▶). For related structures, see: Mitsui et al. (2008 ▶, 2009 ▶); Nakaema et al. (2007 ▶, 2008 ▶); Watanabe et al. (2010a ▶,b ▶).

Experimental

Crystal data

C19H15NO5

M = 337.32

Monoclinic,

a = 8.6877 (6) Å

b = 28.870 (2) Å

c = 6.4635 (5) Å

β = 90.839 (5)°

V = 1621.0 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.84 mm−1

T = 296 K

0.60 × 0.60 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.632, T max = 0.850

29623 measured reflections

2954 independent reflections

2713 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.05

2954 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 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/S1600536810005398/fl2290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005398/fl2290Isup2.hkl

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

C19H15NO5	F(000) = 704
Mr = 337.32	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Melting point: 440 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 8.6877 (6) Å	Cell parameters from 28804 reflections
b = 28.870 (2) Å	θ = 3.1–68.2°
c = 6.4635 (5) Å	µ = 0.84 mm−1
β = 90.839 (5)°	T = 296 K
V = 1621.0 (2) Å3	Platelet, yellow
Z = 4	0.60 × 0.60 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2954 independent reflections
Radiation source: rotating anode	2713 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −34→34
Tmin = 0.632, Tmax = 0.850	l = −7→7
29623 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.3261P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2954 reflections	Δρmax = 0.17 e Å−3
229 parameters	Δρmin = −0.18 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: 0.0064 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.46668 (12)	0.12949 (4)	0.41178 (15)	0.0654 (3)
O2	0.72324 (18)	−0.01707 (5)	−0.4151 (2)	0.0998 (5)
O3	0.86695 (18)	−0.03032 (5)	−0.1503 (3)	0.1103 (5)
O4	0.52962 (12)	0.18647 (4)	−0.08228 (16)	0.0628 (3)
O5	−0.08753 (12)	0.11905 (5)	0.59355 (19)	0.0765 (3)
N1	0.76264 (15)	−0.00977 (4)	−0.2367 (2)	0.0655 (3)
C1	0.32998 (14)	0.15939 (4)	0.12073 (19)	0.0443 (3)
C2	0.37575 (16)	0.18672 (4)	−0.0431 (2)	0.0507 (3)
C3	0.26878 (19)	0.21395 (5)	−0.1541 (2)	0.0639 (4)
H3	0.3001	0.2317	−0.2659	0.077*
C4	0.1186 (2)	0.21401 (5)	−0.0961 (3)	0.0652 (4)
H4	0.0477	0.2313	−0.1726	0.078*
C5	0.06755 (16)	0.18894 (4)	0.0748 (2)	0.0532 (3)
C6	−0.08761 (17)	0.19031 (5)	0.1403 (3)	0.0640 (4)
H6	−0.1591	0.2076	0.0648	0.077*
C7	−0.13369 (16)	0.16718 (6)	0.3093 (3)	0.0650 (4)
H7	−0.2357	0.1689	0.3501	0.078*
C8	−0.02757 (16)	0.14036 (5)	0.4242 (2)	0.0569 (4)
C9	0.12269 (15)	0.13696 (4)	0.3656 (2)	0.0492 (3)
H9	0.1909	0.1185	0.4413	0.059*
C10	0.17471 (14)	0.16139 (4)	0.19014 (19)	0.0445 (3)
C11	0.44394 (14)	0.12808 (4)	0.22566 (19)	0.0447 (3)
C12	0.52624 (13)	0.09236 (4)	0.09933 (18)	0.0418 (3)
C13	0.48124 (15)	0.08167 (4)	−0.1027 (2)	0.0481 (3)
H13	0.3990	0.0974	−0.1642	0.058*
C14	0.55780 (16)	0.04787 (5)	−0.2128 (2)	0.0513 (3)
H14	0.5281	0.0405	−0.3477	0.062*
C15	0.67883 (15)	0.02546 (4)	−0.1175 (2)	0.0488 (3)
C16	0.72680 (15)	0.03499 (5)	0.0825 (2)	0.0529 (3)
H16	0.8093	0.0192	0.1426	0.063*
C17	0.64890 (14)	0.06867 (4)	0.1911 (2)	0.0481 (3)
H17	0.6787	0.0755	0.3264	0.058*
C18	0.5831 (2)	0.20964 (7)	−0.2619 (2)	0.0781 (5)
H18A	0.6892	0.2019	−0.2832	0.094*
H18B	0.5734	0.2425	−0.2436	0.094*
H18C	0.5228	0.2001	−0.3801	0.094*
C19	0.0143 (2)	0.09324 (6)	0.7227 (3)	0.0767 (5)
H19A	−0.0384	0.0838	0.8452	0.092*
H19B	0.1012	0.1121	0.7607	0.092*
H19C	0.0490	0.0663	0.6497	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0595 (6)	0.0914 (8)	0.0453 (5)	0.0172 (5)	−0.0034 (4)	−0.0093 (5)
O2	0.1225 (12)	0.1010 (10)	0.0759 (9)	0.0427 (8)	0.0043 (8)	−0.0265 (7)
O3	0.0969 (10)	0.1002 (10)	0.1330 (13)	0.0545 (8)	−0.0240 (9)	−0.0403 (9)
O4	0.0602 (6)	0.0626 (6)	0.0659 (6)	−0.0045 (5)	0.0160 (5)	0.0089 (5)
O5	0.0524 (6)	0.0989 (9)	0.0787 (8)	−0.0120 (6)	0.0186 (5)	0.0010 (6)
N1	0.0615 (8)	0.0523 (7)	0.0828 (9)	0.0089 (6)	0.0063 (7)	−0.0100 (6)
C1	0.0460 (7)	0.0403 (6)	0.0467 (7)	0.0025 (5)	0.0017 (5)	−0.0048 (5)
C2	0.0564 (8)	0.0431 (6)	0.0527 (7)	−0.0005 (5)	0.0056 (6)	−0.0032 (5)
C3	0.0813 (11)	0.0499 (8)	0.0606 (9)	0.0052 (7)	0.0037 (7)	0.0109 (6)
C4	0.0716 (10)	0.0545 (8)	0.0690 (9)	0.0141 (7)	−0.0105 (8)	0.0069 (7)
C5	0.0526 (8)	0.0455 (7)	0.0612 (8)	0.0076 (5)	−0.0068 (6)	−0.0089 (6)
C6	0.0481 (8)	0.0628 (9)	0.0806 (10)	0.0124 (6)	−0.0127 (7)	−0.0139 (8)
C7	0.0385 (7)	0.0716 (9)	0.0850 (11)	0.0003 (6)	0.0025 (7)	−0.0194 (8)
C8	0.0462 (7)	0.0607 (8)	0.0639 (9)	−0.0073 (6)	0.0069 (6)	−0.0128 (7)
C9	0.0440 (7)	0.0497 (7)	0.0539 (7)	0.0009 (5)	0.0022 (5)	−0.0052 (6)
C10	0.0446 (7)	0.0390 (6)	0.0498 (7)	0.0025 (5)	−0.0012 (5)	−0.0092 (5)
C11	0.0393 (6)	0.0501 (7)	0.0446 (7)	−0.0017 (5)	0.0020 (5)	−0.0009 (5)
C12	0.0385 (6)	0.0413 (6)	0.0455 (6)	−0.0021 (5)	0.0026 (5)	0.0037 (5)
C13	0.0451 (7)	0.0506 (7)	0.0486 (7)	0.0068 (5)	−0.0027 (5)	0.0007 (5)
C14	0.0549 (7)	0.0511 (7)	0.0478 (7)	0.0018 (6)	0.0011 (6)	−0.0025 (5)
C15	0.0464 (7)	0.0401 (6)	0.0602 (8)	0.0003 (5)	0.0092 (6)	−0.0004 (5)
C16	0.0456 (7)	0.0482 (7)	0.0647 (8)	0.0066 (5)	−0.0025 (6)	0.0067 (6)
C17	0.0467 (7)	0.0495 (7)	0.0480 (7)	0.0002 (5)	−0.0024 (5)	0.0047 (5)
C18	0.0854 (12)	0.0950 (12)	0.0545 (9)	−0.0255 (10)	0.0178 (8)	−0.0001 (8)
C19	0.0776 (11)	0.0812 (11)	0.0720 (11)	−0.0124 (9)	0.0217 (9)	0.0066 (9)

O1—C11	1.2169 (15)	C7—H7	0.9300
O2—N1	1.2163 (18)	C8—C9	1.3681 (19)
O3—N1	1.2126 (18)	C9—C10	1.4151 (18)
O4—C2	1.3641 (17)	C9—H9	0.9300
O4—C18	1.4239 (18)	C11—C12	1.5027 (17)
O5—C8	1.3656 (18)	C12—C17	1.3917 (17)
O5—C19	1.419 (2)	C12—C13	1.3923 (18)
N1—C15	1.4748 (17)	C13—C14	1.3837 (18)
C1—C2	1.3837 (18)	C13—H13	0.9300
C1—C10	1.4290 (17)	C14—C15	1.3730 (19)
C1—C11	1.4960 (17)	C14—H14	0.9300
C2—C3	1.406 (2)	C15—C16	1.380 (2)
C3—C4	1.363 (2)	C16—C17	1.3820 (19)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.398 (2)	C17—H17	0.9300
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.420 (2)	C18—H18B	0.9600
C5—C10	1.4265 (18)	C18—H18C	0.9600
C6—C7	1.346 (2)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.408 (2)	C19—H19C	0.9600
C2—O4—C18	118.76 (13)	C5—C10—C1	118.05 (12)
C8—O5—C19	117.80 (12)	O1—C11—C1	121.65 (11)
O3—N1—O2	123.34 (14)	O1—C11—C12	119.24 (11)
O3—N1—C15	117.93 (14)	C1—C11—C12	119.03 (10)
O2—N1—C15	118.72 (13)	C17—C12—C13	119.56 (11)
C2—C1—C10	120.03 (12)	C17—C12—C11	118.24 (11)
C2—C1—C11	119.73 (11)	C13—C12—C11	122.17 (11)
C10—C1—C11	120.24 (11)	C14—C13—C12	120.55 (12)
O4—C2—C1	115.61 (12)	C14—C13—H13	119.7
O4—C2—C3	123.40 (12)	C12—C13—H13	119.7
C1—C2—C3	120.94 (13)	C15—C14—C13	118.17 (12)
C4—C3—C2	119.23 (13)	C15—C14—H14	120.9
C4—C3—H3	120.4	C13—C14—H14	120.9
C2—C3—H3	120.4	C14—C15—C16	123.05 (12)
C3—C4—C5	122.22 (14)	C14—C15—N1	118.11 (12)
C3—C4—H4	118.9	C16—C15—N1	118.83 (12)
C5—C4—H4	118.9	C15—C16—C17	118.19 (12)
C4—C5—C6	122.36 (14)	C15—C16—H16	120.9
C4—C5—C10	119.29 (13)	C17—C16—H16	120.9
C6—C5—C10	118.34 (14)	C16—C17—C12	120.47 (12)
C7—C6—C5	121.57 (14)	C16—C17—H17	119.8
C7—C6—H6	119.2	C12—C17—H17	119.8
C5—C6—H6	119.2	O4—C18—H18A	109.5
C6—C7—C8	120.05 (13)	O4—C18—H18B	109.5
C6—C7—H7	120.0	H18A—C18—H18B	109.5
C8—C7—H7	120.0	O4—C18—H18C	109.5
O5—C8—C9	124.50 (14)	H18A—C18—H18C	109.5
O5—C8—C7	114.60 (13)	H18B—C18—H18C	109.5
C9—C8—C7	120.90 (14)	O5—C19—H19A	109.5
C8—C9—C10	120.22 (13)	O5—C19—H19B	109.5
C8—C9—H9	119.9	H19A—C19—H19B	109.5
C10—C9—H9	119.9	O5—C19—H19C	109.5
C9—C10—C5	118.89 (12)	H19A—C19—H19C	109.5
C9—C10—C1	123.06 (11)	H19B—C19—H19C	109.5
C18—O4—C2—C1	173.20 (13)	C2—C1—C10—C9	−175.40 (12)
C18—O4—C2—C3	−9.2 (2)	C11—C1—C10—C9	4.15 (18)
C10—C1—C2—O4	172.62 (11)	C2—C1—C10—C5	5.40 (17)
C11—C1—C2—O4	−6.93 (17)	C11—C1—C10—C5	−175.06 (11)
C10—C1—C2—C3	−5.08 (19)	C2—C1—C11—O1	125.86 (14)
C11—C1—C2—C3	175.38 (12)	C10—C1—C11—O1	−53.69 (17)
O4—C2—C3—C4	−176.15 (14)	C2—C1—C11—C12	−57.33 (16)
C1—C2—C3—C4	1.4 (2)	C10—C1—C11—C12	123.12 (12)
C2—C3—C4—C5	2.0 (2)	O1—C11—C12—C17	−13.28 (17)
C3—C4—C5—C6	177.57 (14)	C1—C11—C12—C17	169.84 (11)
C3—C4—C5—C10	−1.5 (2)	O1—C11—C12—C13	165.11 (12)
C4—C5—C6—C7	−177.73 (14)	C1—C11—C12—C13	−11.77 (17)
C10—C5—C6—C7	1.4 (2)	C17—C12—C13—C14	−0.26 (19)
C5—C6—C7—C8	−0.8 (2)	C11—C12—C13—C14	−178.63 (11)
C19—O5—C8—C9	2.9 (2)	C12—C13—C14—C15	−0.14 (19)
C19—O5—C8—C7	−176.97 (14)	C13—C14—C15—C16	0.3 (2)
C6—C7—C8—O5	179.19 (13)	C13—C14—C15—N1	−178.58 (12)
C6—C7—C8—C9	−0.7 (2)	O3—N1—C15—C14	−178.16 (15)
O5—C8—C9—C10	−178.35 (12)	O2—N1—C15—C14	1.2 (2)
C7—C8—C9—C10	1.5 (2)	O3—N1—C15—C16	2.9 (2)
C8—C9—C10—C5	−0.86 (18)	O2—N1—C15—C16	−177.70 (14)
C8—C9—C10—C1	179.93 (12)	C14—C15—C16—C17	0.0 (2)
C4—C5—C10—C9	178.59 (12)	N1—C15—C16—C17	178.86 (11)
C6—C5—C10—C9	−0.53 (18)	C15—C16—C17—C12	−0.44 (19)
C4—C5—C10—C1	−2.16 (18)	C13—C12—C17—C16	0.55 (18)
C6—C5—C10—C1	178.71 (11)	C11—C12—C17—C16	178.99 (11)

Cg1 is the centroid of the naphthalene ring system C1–C10.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1i	0.93	2.81	3.5789 (15)	141
C19—H19B···Cg1ii	0.96	2.91	3.7605 (19)	148
C18—H18C···O1iii	0.96	2.49	3.281 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the naphthalene ring system C1–C5,C10.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.93	2.81	3.5789 (15)	141
C19—H19B⋯Cg1ii	0.96	2.91	3.7605 (19)	148
C18—H18C⋯O1iii	0.96	2.49	3.281 (2)	140

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