2,7-Dimethoxy­-1-(4-nitro­benzo­yl)-naphthalene

Watanabe, S.; Nakaema, K.; Nishijima, T.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810005398

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o615

doi:10.1107/S1600536810005398

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2,7-Dimethoxy-1-(4-nitrobenzoyl)-naphthalene

Shoji Watanabe,^a Kosuke Nakaema,^a Takahiro Nishijima,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 22 January 2010; accepted 9 February 2010; online 13 February 2010)

In the title compound, C₁₉H₁₅NO₅, 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, molecules are linked by C—H⋯π interactions and the phenyl rings are involved in a centrosymmetric π–π interaction with a perpendicular distance of 3.523 Å and a lateral offset of 1.497 Å. In addition, weak intermolecular C—H⋯O hydrogen bonds are formed between an H atom of one methoxy 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_r = 337.32
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.05
2954 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) x, y, z-1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005398/fl2290sup1.cif

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

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are twisted almost perpendicularly but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings. Recently, we reported the structures of 1,8-diaroyl-2,7-dimethoxynaphthalenes, i. e., 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorobenzoyl)dimethanone (Watanabe et al., 2010a) and bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al., 2010b). Furthermore, the crystal structures of 1-aroyl-2,7-dimethoxynaphthalenes, i. e., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al., 2008) and (4-chlorobenzoyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al. 2009), also exhibit essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. As a part of our ongoing studies on the formation and the structure of the aroylated naphthalene derivatives, the synthesis and crystal structure of (I), a 1-monoaroylnaphthalene bearing nitro group, is discussed in this report. (I) was prepared by electrophilic aromatic aroylation reaction of 2,7-dimethoxynaphthalene with 4-nitrobenzoyl chloride.

The molecular structure of (I) is displayed in Fig. 1. The interplanar angle between the benzene ring (C12—C17) and the naphthalene ring (C1—C10) is 61.97 (5)°. The dihedral angle between the carbonyl and the naphthalene is 54.68 (6)° [C10—C1—C11—O1 torsion angle = -53.67 (17)°]. On the other hand, the dihedral angle between the carbonyl group and the phenyl ring is 12.54 (7)° [O1—C11—C12—C17 torsion angle = -13.29 (17)°]. The nitro group and the phenyl group are almost coplanar [O3—N1—C15—C14 torsion angle = 2.94 (19)°].

The molecular packing of (I) is mainly stabilized by van der Waals interactions. The molecules are aligned consecutively in stacks along the c axis (Fig. 2). Adjacent 4-nitrophenyl groups related by crystallographic inversion centers are exactly antiparallel and the perpendicular distance between the mean planes is 3.523 Å (Fig. 3). The centroid-centroid distance between the two antiparallel phenyl rings is 3.8283 (8) Å and the lateral offset is 1.497 Å, indicating the presence of a π–π interaction.

Moreover, molecules are linked by two types of C—H···π interactions. The naphthalene ring acts as a hydrogen-bond donor and the π system of the naphthalene ring [C1—C10 ring (with centroid Cg1)] of an adjacent molecule acts as an accepter (C3—H3···πⁱ) (Fig. 4). The methyl group acts as a hydrogen-bond donor and the π system of the naphthalene ring [C1—C10 ring (with centroid Cg1)] of an adjacent molecule acts as an accepter (C19—H19C···πⁱⁱ) .

The crystal packing is additionally stabilized by intermolecular weak C—H···O hydrogen bonding between the carbonyl oxygen and a hydrogen atom of a nearby methyl group (C18—H18B···O1ⁱⁱⁱ; Fig. 4 and Table 1).

Related literature top

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 top

The title compound was prepared by treatment of a mixture of 2,7-dimethoxynaphthalene (1.0 mmol) and 4-nitrobenzoic acid (2.2 mmol) with phosphorus pentoxide–methanesulfonic acid mixture (P₂O₅–MsOH [1/10 w/w]; 4.4 ml) at 40°C for 0.5 hours followed by a typical work-up procedure (50% yield; Okamoto & Yonezawa, 2009). Yellow platelet single crystals suitable for X-ray diffraction were obtained by recrystallization from chloroform.

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 3.76 (3H, s), 3.76 (3H, s), 6.87 (1H, d, J = 2.3 Hz), 7.05 (1H, dd, J = 9.0, 2.3 Hz), 7.16 (1H, d, J = 9.0 Hz), 7.75 (1H, d, J = 8.7 Hz), 7.93 (1H, d, J = 9.0 Hz), 7.98 (2H, d, J = 9.0 Hz), 8.27 (2H, d, J = 8.7 Hz); ¹³C NMR (75 MHz, CDCl₃) δ 21.8, 22.7, 68.3, 76.4, 82.5, 83.9, 90.3, 91.0, 95.7, 96.5, 96.7, 98.8, 99.6, 109.6, 122.3, 126.0, 162.9; IR (KBr): 1357, 1594, 1267; Anal. Calcd for C₁₉H₁₅NO₅: C 67.65, H 4.48, N 4.15. Found: C 67.52, H 4.51, N 4.06.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The alignment of the molecules in the crystal structure, viewed along c axis.
	Fig. 3. Side-on view of the π–π interaction.
	Fig. 4. Two types of C—H···π interactions (Green Copper dotted lines, Violet Red dotted lines) and weak C—H···O interactions (Blue dotted lines).

2,7-Dimethoxy-1-(4-nitrobenzoyl)-naphthalene top

Crystal data top

C₁₉H₁₅NO₅	F(000) = 704
M_r = 337.32	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	2954 independent reflections
Radiation source: rotating anode	2713 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 3.1°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −34→34
T_min = 0.632, T_max = 0.850	l = −7→7
29623 measured reflections

Refinement top

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(F_o²) + (0.0491P)² + 0.3261P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2954 reflections	Δρ_max = 0.17 e Å⁻³
229 parameters	Δρ_min = −0.19 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)

Crystal data top

C₁₉H₁₅NO₅	V = 1621.0 (2) Å³
M_r = 337.32	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.6877 (6) Å	µ = 0.84 mm⁻¹
b = 28.870 (2) Å	T = 296 K
c = 6.4635 (5) Å	0.60 × 0.60 × 0.20 mm
β = 90.839 (5)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2954 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2713 reflections with I > 2σ(I)
T_min = 0.632, T_max = 0.850	R_int = 0.033
29623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.05	Δρ_max = 0.17 e Å⁻³
2954 reflections	Δρ_min = −0.19 e Å⁻³
229 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z+1; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO₅
M_r	337.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.6877 (6), 28.870 (2), 6.4635 (5)
β (°)	90.839 (5)
V (Å³)	1621.0 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.60 × 0.60 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.632, 0.850
No. of measured, independent and observed [I > 2σ(I)] reflections	29623, 2954, 2713
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.05
No. of reflections	2954
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z+1; (iii) x, y, z−1.

Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi for technical advice. This work was partially supported by the Iketani Science and Technology Foundation, Tokyo, Japan.

References

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