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organic compounds
(4-Chlorophenyl)(2,7-dimethoxy-8-nitronaphthalen-1-yl)methanone
aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
*Correspondence e-mail: aokamoto@cc.tuat.ac.jp
In the title compound, C19H14ClNO5, the aroyl group is attached to the naphthalene ring system with a non-coplanar configuration. The dihedral angle between naphthalene ring system and benzene ring is 70.62 (6)°. The nitro group is oriented in parallel with the adjacent carbonyl plane. The torsion angle of the carbonyl group and naphthalene ring is 54.68 (19)° (C—C—C—O), and that of nitro group and naphthalene ring is 54.26 (18)° (O—N—C—C). In the crystal, π–π interactions between naphthalene systems [centroid–centroid distances = 3.5633 (9), 3,5634 (9), and 3.9758(9) Å], C—H⋯O hydrogen bonds, intermolecular N—O⋯Cl interactions [2.9937 (12) Å] and C—H⋯π contacts are observed.
Related literature
For electrophilic aromatic substitution of naphthalene derivatives giving aryl naphthyl ketone compounds, see: Okamoto & Yonezawa (2009). For related structures, see: Kato et al. (2010
); Mitsui et al. (2008
, 2010
); Nishijima et al. (2010
); Watanabe et al. (2010
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: PROCESS-AUTO (Rigaku, 1998); cell 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: ORTEP (Burnett & Johnson, 1996
); software used to prepare material for publication: CrystalStructure.
Supporting information
https://doi.org/10.1107/S1600536810051998/om2387sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051998/om2387Isup2.hkl
To a solution of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (653.4 mg, 2.0 mmol) in methylene chloride (10 ml), aqueous 61% nitric acid (2.0 ml) was dropped by portions at 273 K. After the reaction mixture was stirred at 273 K for 2 h, it was poured into ice-cold water (25 ml). The aqueous solution was extracted with CHCl3(15 ml × 3). The combined extracts were washed with water followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give cake. The crude product was purified by
(good solvent:CHCl3, poor solvent:hexane) and (silica gel, CHCl3) (isolated yield 448.8 mg, 60%). Single crystals suitable for X-ray were obtained by crystallization from acetone as yellow plates.Spectral data: 1H NMR δ (300 MHz, CDCl3); 3.73 (3H, s), 3.97 (3H, s), 7.22 (1H, d, J = 9.3 Hz), 7.24 (1H, d, J = 8.6 Hz), 7.38 (2H, d, J = 8.9 Hz), 7.82 (2H, d, J = 8.6 Hz), 7.95 (1H, d, J = 9.3 Hz), 7.96 (1H, d, J = 8.9 Hz). 13C NMR δ (75 MHz, CDCl3); 56.48, 57.22, 111.26, 111.86, 118.02, 124.16, 124.59, 128.64, 130.51, 132.59, 133.24, 134.39, 136.79, 139.17, 151.61, 157.76, 193.23. IR (KBr); 1655 (C=O), 1623 (Ar), 1527 (Ar), 1372 (NO2), 1275 (O—Me) cm-1. HRMS (m/z); [M + H]+ Calcd for C19H15ClNO5, 272.0639; found, 272.0601. m.p. = 483.1–486.4 K.
All H atoms were found in a difference map and were subsequently refined as riding atoms, with C—H = 0.93 (aromatic) Å and C—H = 0.96 (methyl) Å, and with Uiso(H) = 1.2Ueq(C).
In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene homologues exemplified by 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010). The aromatic rings in these molecules are arranged in a non-coplanar alignment to each other. Furthermore, we have also clarified the crystal structures of 1-monoaroylated naphthalene compounds. They have essentially the same non-coplanar structure with the 1,8-diaroylated naphthalene, e.g., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al., 2008), 2,7-dimethoxy-1-(4-nitrobenzoyl)naphthalene (Watanabe et al., 2010) and (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (Kato, et al., 2010). In the course of this work, we have revealed the
of 1-monoaroylnaphthalene compounds having a substituent, other than aroyl group, at the 8-position such as (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone (Mitsui, Nagasawa, Watanabe et al. 2010). The aroyl group and naphthalene ring in these molecules have similar configuration to 1,8-diaroylated naphthalene. As a part of our continuous study on the molecular structures of these kinds of homologous molecules, the of title compound, a 1-chlorobenzoylated naphthalene bearing nitro group at the 8-position, is discussed in this report.An ORTEP (Burnett & Johnson, 1996) plot of the title compound is displayed in Fig. 1. In the molecule, the dihedral angle between the benzene ring (C11—C16) and the naphthalene ring (C1—C10) is 70.62 (6)°. The nitro group are also twisted away from the naphthalene ring system, then the nitro group and the carbonyl group are arranged almost in parallel. The dihedral angle between the ketonic C=O plane (O3/C1/C11/C17) and naphthalene ring (C1—C10) is 60.33 (7)° [C9—C1—C17—O3 torsion angle is 54.68 (19)°] and between the nitro plane (O4/O5/N1/C8) and naphthalene ring (C1—C10) is 57.34 (8)° [O4—N1—C8—O9 torsion angle is 54.26 (18)°]. On the other hand, the carbonyl group and the 4-chlorophenyl one have almost coplanar configuration [C16—C11—C17—O3 torsion angle is 10.5 (2)°], but the torsion angle is larger than those of another homologous compounds, i.e., the torsion angles of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene and (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone are -4.4 (2)° and -3.6 (4)°, respectively.
The molecular packing of the title compound is mainly stabilized by weak intermolecular hydrogen bonds and van der Waals interactions. The 4-chlorophenyl groups interact with the nitro groups [C13—H13···O5 is 2.44 Å; (i) x, 3/2 - y, 1/2 + z] of adjacent molecules along the c axis (Fig. 2). Interaction between the methoxy groups and the carbonyl groups [C18—H18C···O3 = 2.51 Å; (i) x, 3/2 - y, 1/2 + z] form naphthalene ring systems into zigzag arrangement (Fig. 2). On the other hand, C—H···π interaction and π–π interactions deposit layer upon layer of naphthalene rings [C1/C2/C3/C4/C9/C10 ring with centroid Cg1 and C5-C10 ring with centroid Cg2 (Fig. 3). Furthermore, O4 and C11 interact with each other [O4···Cl1 = 2.9937 (12) Å; (iii) 2 - x, -y, 1-z] (Fig. 4).
For electrophilic aromatic substitution of naphthalene derivatives giving aryl naphthyl ketone compounds, see: Okamoto & Yonezawa (2009). For the structures of closely related compounds, see: Kato et al. (2010); Mitsui et al. (2008); Mitsui et al. (2010); Nishijima et al. (2010); Watanabe et al. (2010).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
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: ORTEP (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).C19H14ClNO5 | F(000) = 768 |
Mr = 371.76 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/c | Melting point = 486.4–483.1 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54187 Å |
a = 8.57511 (16) Å | Cell parameters from 22820 reflections |
b = 14.0424 (3) Å | θ = 3.1–68.2° |
c = 14.0842 (3) Å | µ = 2.31 mm−1 |
β = 100.206 (1)° | T = 193 K |
V = 1669.12 (5) Å3 | Platelet, yellow |
Z = 4 | 0.60 × 0.40 × 0.30 mm |
Rigaku R-AXIS RAPID diffractometer | 3058 independent reflections |
Radiation source: fine-focus sealed tube | 2793 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.00 pixels mm-1 | θmax = 68.2°, θmin = 4.5° |
ω scans | h = −10→10 |
Absorption correction: numerical (NUMABS; Higashi, 1999) | k = −16→16 |
Tmin = 0.294, Tmax = 0.544 | l = −16→16 |
29408 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) = 0.093 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.5094P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3058 reflections | Δρmax = 0.21 e Å−3 |
238 parameters | Δρmin = −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: 0.0049 (3) |
C19H14ClNO5 | V = 1669.12 (5) Å3 |
Mr = 371.76 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 8.57511 (16) Å | µ = 2.31 mm−1 |
b = 14.0424 (3) Å | T = 193 K |
c = 14.0842 (3) Å | 0.60 × 0.40 × 0.30 mm |
β = 100.206 (1)° |
Rigaku R-AXIS RAPID diffractometer | 3058 independent reflections |
Absorption correction: numerical (NUMABS; Higashi, 1999) | 2793 reflections with I > 2σ(I) |
Tmin = 0.294, Tmax = 0.544 | Rint = 0.028 |
29408 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.21 e Å−3 |
3058 reflections | Δρmin = −0.19 e Å−3 |
238 parameters |
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 | ||
Cl1 | 0.16621 (6) | 1.13841 (3) | 0.55672 (4) | 0.06727 (18) | |
O1 | 0.57537 (12) | 0.75406 (7) | 0.62980 (7) | 0.0434 (3) | |
O2 | −0.00458 (14) | 0.47410 (8) | 0.31568 (8) | 0.0511 (3) | |
O3 | 0.41091 (13) | 0.73567 (8) | 0.38109 (7) | 0.0468 (3) | |
O4 | 0.06202 (13) | 0.71291 (7) | 0.40079 (8) | 0.0485 (3) | |
O5 | 0.11487 (19) | 0.64395 (9) | 0.27365 (8) | 0.0676 (4) | |
N1 | 0.11528 (15) | 0.64617 (8) | 0.35979 (9) | 0.0412 (3) | |
C1 | 0.38260 (16) | 0.66673 (10) | 0.52900 (9) | 0.0338 (3) | |
C2 | 0.49357 (17) | 0.67065 (10) | 0.61336 (10) | 0.0360 (3) | |
C3 | 0.52689 (18) | 0.59082 (11) | 0.67462 (10) | 0.0405 (3) | |
H3 | 0.5989 | 0.5956 | 0.7322 | 0.049* | |
C4 | 0.45238 (18) | 0.50699 (11) | 0.64837 (11) | 0.0415 (3) | |
H4 | 0.4776 | 0.4538 | 0.6873 | 0.050* | |
C5 | 0.26174 (18) | 0.41072 (10) | 0.53798 (11) | 0.0408 (3) | |
H5 | 0.2885 | 0.3585 | 0.5781 | 0.049* | |
C6 | 0.15099 (18) | 0.39956 (10) | 0.45694 (11) | 0.0410 (3) | |
H6 | 0.1042 | 0.3404 | 0.4419 | 0.049* | |
C7 | 0.10756 (17) | 0.47805 (10) | 0.39587 (10) | 0.0377 (3) | |
C8 | 0.17971 (16) | 0.56535 (9) | 0.42014 (9) | 0.0347 (3) | |
C9 | 0.29884 (16) | 0.57978 (9) | 0.50291 (9) | 0.0329 (3) | |
C10 | 0.33774 (17) | 0.49855 (10) | 0.56356 (10) | 0.0366 (3) | |
C11 | 0.32856 (16) | 0.84584 (9) | 0.48861 (10) | 0.0350 (3) | |
C12 | 0.25859 (19) | 0.86117 (10) | 0.56900 (11) | 0.0427 (3) | |
H12 | 0.2450 | 0.8103 | 0.6090 | 0.051* | |
C13 | 0.2088 (2) | 0.95114 (11) | 0.59030 (12) | 0.0470 (4) | |
H13 | 0.1618 | 0.9612 | 0.6441 | 0.056* | |
C14 | 0.23033 (19) | 1.02564 (10) | 0.53021 (12) | 0.0457 (4) | |
C15 | 0.3010 (2) | 1.01289 (11) | 0.45082 (12) | 0.0501 (4) | |
H15 | 0.3156 | 1.0642 | 0.4116 | 0.060* | |
C16 | 0.35004 (18) | 0.92290 (11) | 0.43016 (11) | 0.0423 (3) | |
H16 | 0.3980 | 0.9136 | 0.3766 | 0.051* | |
C17 | 0.37585 (16) | 0.74943 (10) | 0.46024 (10) | 0.0350 (3) | |
C18 | 0.6731 (2) | 0.76752 (13) | 0.72157 (11) | 0.0501 (4) | |
H18A | 0.7157 | 0.8309 | 0.7256 | 0.060* | |
H18B | 0.7584 | 0.7223 | 0.7296 | 0.060* | |
H18C | 0.6113 | 0.7584 | 0.7714 | 0.060* | |
C19 | −0.0836 (2) | 0.38502 (13) | 0.29095 (13) | 0.0560 (4) | |
H19A | −0.1582 | 0.3921 | 0.2319 | 0.067* | |
H19B | −0.1386 | 0.3661 | 0.3416 | 0.067* | |
H19C | −0.0069 | 0.3373 | 0.2827 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0844 (3) | 0.0300 (2) | 0.0792 (3) | 0.01301 (19) | −0.0079 (2) | −0.01089 (18) |
O1 | 0.0501 (6) | 0.0388 (6) | 0.0398 (5) | −0.0041 (4) | 0.0037 (4) | 0.0022 (4) |
O2 | 0.0594 (7) | 0.0403 (6) | 0.0494 (6) | −0.0012 (5) | −0.0019 (5) | −0.0042 (5) |
O3 | 0.0609 (7) | 0.0426 (6) | 0.0418 (6) | 0.0080 (5) | 0.0226 (5) | 0.0057 (4) |
O4 | 0.0506 (6) | 0.0319 (5) | 0.0630 (7) | 0.0123 (4) | 0.0101 (5) | −0.0006 (5) |
O5 | 0.1160 (12) | 0.0474 (7) | 0.0355 (6) | 0.0052 (7) | 0.0027 (6) | 0.0034 (5) |
N1 | 0.0494 (7) | 0.0325 (6) | 0.0400 (7) | 0.0050 (5) | 0.0031 (5) | 0.0014 (5) |
C1 | 0.0396 (7) | 0.0292 (7) | 0.0349 (7) | 0.0073 (5) | 0.0134 (5) | 0.0021 (5) |
C2 | 0.0401 (7) | 0.0335 (7) | 0.0366 (7) | 0.0037 (6) | 0.0128 (6) | 0.0006 (5) |
C3 | 0.0434 (8) | 0.0412 (8) | 0.0368 (7) | 0.0069 (6) | 0.0072 (6) | 0.0046 (6) |
C4 | 0.0472 (8) | 0.0360 (8) | 0.0421 (8) | 0.0097 (6) | 0.0106 (6) | 0.0102 (6) |
C5 | 0.0505 (8) | 0.0282 (7) | 0.0463 (8) | 0.0070 (6) | 0.0157 (7) | 0.0067 (6) |
C6 | 0.0488 (8) | 0.0283 (7) | 0.0488 (8) | 0.0015 (6) | 0.0164 (7) | −0.0014 (6) |
C7 | 0.0415 (8) | 0.0342 (7) | 0.0393 (7) | 0.0055 (6) | 0.0126 (6) | −0.0030 (6) |
C8 | 0.0420 (7) | 0.0287 (7) | 0.0356 (7) | 0.0086 (5) | 0.0128 (6) | 0.0017 (5) |
C9 | 0.0387 (7) | 0.0289 (7) | 0.0341 (7) | 0.0079 (5) | 0.0144 (5) | 0.0017 (5) |
C10 | 0.0427 (8) | 0.0313 (7) | 0.0382 (7) | 0.0086 (6) | 0.0140 (6) | 0.0047 (5) |
C11 | 0.0370 (7) | 0.0296 (7) | 0.0375 (7) | 0.0001 (5) | 0.0046 (5) | 0.0030 (5) |
C12 | 0.0536 (9) | 0.0304 (7) | 0.0467 (8) | 0.0022 (6) | 0.0154 (7) | 0.0029 (6) |
C13 | 0.0555 (9) | 0.0356 (8) | 0.0515 (9) | 0.0040 (7) | 0.0138 (7) | −0.0053 (7) |
C14 | 0.0490 (9) | 0.0272 (7) | 0.0552 (9) | 0.0027 (6) | −0.0061 (7) | −0.0038 (6) |
C15 | 0.0652 (10) | 0.0301 (8) | 0.0511 (9) | −0.0034 (7) | −0.0002 (8) | 0.0095 (6) |
C16 | 0.0498 (8) | 0.0359 (8) | 0.0406 (7) | −0.0023 (6) | 0.0063 (6) | 0.0056 (6) |
C17 | 0.0375 (7) | 0.0330 (7) | 0.0360 (7) | 0.0013 (6) | 0.0102 (6) | 0.0028 (5) |
C18 | 0.0544 (9) | 0.0530 (9) | 0.0413 (8) | −0.0073 (8) | 0.0043 (7) | −0.0016 (7) |
C19 | 0.0566 (10) | 0.0471 (9) | 0.0616 (10) | −0.0032 (8) | 0.0026 (8) | −0.0134 (8) |
Cl1—C14 | 1.7384 (15) | C6—H6 | 0.9300 |
O1—C2 | 1.3639 (17) | C7—C8 | 1.388 (2) |
O1—C18 | 1.4230 (18) | C8—C9 | 1.422 (2) |
O2—C7 | 1.3485 (18) | C9—C10 | 1.4287 (18) |
O2—C19 | 1.436 (2) | C11—C12 | 1.389 (2) |
O3—C17 | 1.2202 (16) | C11—C16 | 1.3914 (19) |
O4—N1 | 1.2303 (15) | C11—C17 | 1.4882 (19) |
O5—N1 | 1.2130 (16) | C12—C13 | 1.383 (2) |
N1—C8 | 1.4661 (17) | C12—H12 | 0.9300 |
C1—C2 | 1.385 (2) | C13—C14 | 1.378 (2) |
C1—C9 | 1.4311 (19) | C13—H13 | 0.9300 |
C1—C17 | 1.5066 (18) | C14—C15 | 1.375 (2) |
C2—C3 | 1.413 (2) | C15—C16 | 1.379 (2) |
C3—C4 | 1.359 (2) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C10 | 1.411 (2) | C18—H18A | 0.9600 |
C4—H4 | 0.9300 | C18—H18B | 0.9600 |
C5—C6 | 1.358 (2) | C18—H18C | 0.9600 |
C5—C10 | 1.412 (2) | C19—H19A | 0.9600 |
C5—H5 | 0.9300 | C19—H19B | 0.9600 |
C6—C7 | 1.407 (2) | C19—H19C | 0.9600 |
C2—O1—C18 | 118.08 (11) | C4—C10—C9 | 119.53 (13) |
C7—O2—C19 | 118.35 (12) | C12—C11—C16 | 118.90 (13) |
O5—N1—O4 | 123.61 (12) | C12—C11—C17 | 122.51 (12) |
O5—N1—C8 | 119.60 (12) | C16—C11—C17 | 118.54 (12) |
O4—N1—C8 | 116.79 (11) | C13—C12—C11 | 120.84 (14) |
C2—C1—C9 | 119.42 (12) | C13—C12—H12 | 119.6 |
C2—C1—C17 | 117.58 (13) | C11—C12—H12 | 119.6 |
C9—C1—C17 | 122.15 (12) | C14—C13—C12 | 118.70 (15) |
O1—C2—C1 | 115.73 (12) | C14—C13—H13 | 120.7 |
O1—C2—C3 | 122.38 (13) | C12—C13—H13 | 120.7 |
C1—C2—C3 | 121.75 (14) | C15—C14—C13 | 121.78 (14) |
C4—C3—C2 | 119.12 (14) | C15—C14—Cl1 | 119.68 (12) |
C4—C3—H3 | 120.4 | C13—C14—Cl1 | 118.54 (13) |
C2—C3—H3 | 120.4 | C14—C15—C16 | 119.06 (14) |
C3—C4—C10 | 121.77 (13) | C14—C15—H15 | 120.5 |
C3—C4—H4 | 119.1 | C16—C15—H15 | 120.5 |
C10—C4—H4 | 119.1 | C15—C16—C11 | 120.70 (14) |
C6—C5—C10 | 122.53 (13) | C15—C16—H16 | 119.6 |
C6—C5—H5 | 118.7 | C11—C16—H16 | 119.6 |
C10—C5—H5 | 118.7 | O3—C17—C11 | 120.81 (12) |
C5—C6—C7 | 119.55 (14) | O3—C17—C1 | 118.53 (12) |
C5—C6—H6 | 120.2 | C11—C17—C1 | 120.66 (11) |
C7—C6—H6 | 120.2 | O1—C18—H18A | 109.5 |
O2—C7—C8 | 117.58 (12) | O1—C18—H18B | 109.5 |
O2—C7—C6 | 123.50 (13) | H18A—C18—H18B | 109.5 |
C8—C7—C6 | 118.88 (14) | O1—C18—H18C | 109.5 |
C7—C8—C9 | 123.49 (12) | H18A—C18—H18C | 109.5 |
C7—C8—N1 | 115.79 (12) | H18B—C18—H18C | 109.5 |
C9—C8—N1 | 120.47 (12) | O2—C19—H19A | 109.5 |
C8—C9—C10 | 115.73 (12) | O2—C19—H19B | 109.5 |
C8—C9—C1 | 125.95 (12) | H19A—C19—H19B | 109.5 |
C10—C9—C1 | 118.31 (13) | O2—C19—H19C | 109.5 |
C5—C10—C4 | 120.69 (13) | H19A—C19—H19C | 109.5 |
C5—C10—C9 | 119.78 (13) | H19B—C19—H19C | 109.5 |
C18—O1—C2—C1 | 170.71 (12) | C2—C1—C9—C10 | −2.42 (18) |
C18—O1—C2—C3 | −13.54 (19) | C17—C1—C9—C10 | 166.79 (12) |
C9—C1—C2—O1 | 175.92 (11) | C6—C5—C10—C4 | −179.90 (13) |
C17—C1—C2—O1 | 6.22 (17) | C6—C5—C10—C9 | −0.1 (2) |
C9—C1—C2—C3 | 0.14 (19) | C3—C4—C10—C5 | −179.85 (13) |
C17—C1—C2—C3 | −169.56 (12) | C3—C4—C10—C9 | 0.4 (2) |
O1—C2—C3—C4 | −173.05 (12) | C8—C9—C10—C5 | 1.55 (18) |
C1—C2—C3—C4 | 2.4 (2) | C1—C9—C10—C5 | −177.58 (12) |
C2—C3—C4—C10 | −2.7 (2) | C8—C9—C10—C4 | −178.68 (12) |
C10—C5—C6—C7 | −0.7 (2) | C1—C9—C10—C4 | 2.19 (19) |
C19—O2—C7—C8 | −178.28 (13) | C16—C11—C12—C13 | 0.9 (2) |
C19—O2—C7—C6 | −0.3 (2) | C17—C11—C12—C13 | −176.66 (14) |
C5—C6—C7—O2 | −177.91 (13) | C11—C12—C13—C14 | −0.1 (2) |
C5—C6—C7—C8 | 0.1 (2) | C12—C13—C14—C15 | −0.7 (2) |
O2—C7—C8—C9 | 179.59 (12) | C12—C13—C14—Cl1 | 179.50 (13) |
C6—C7—C8—C9 | 1.5 (2) | C13—C14—C15—C16 | 0.8 (2) |
O2—C7—C8—N1 | 5.20 (18) | Cl1—C14—C15—C16 | −179.43 (12) |
C6—C7—C8—N1 | −172.92 (12) | C14—C15—C16—C11 | 0.0 (2) |
O5—N1—C8—C7 | −58.76 (19) | C12—C11—C16—C15 | −0.8 (2) |
O4—N1—C8—C7 | 120.32 (14) | C17—C11—C16—C15 | 176.83 (14) |
O5—N1—C8—C9 | 126.67 (15) | C12—C11—C17—O3 | 167.06 (14) |
O4—N1—C8—C9 | −54.26 (18) | C16—C11—C17—O3 | −10.5 (2) |
C7—C8—C9—C10 | −2.25 (19) | C12—C11—C17—C1 | −13.4 (2) |
N1—C8—C9—C10 | 171.89 (12) | C16—C11—C17—C1 | 169.08 (13) |
C7—C8—C9—C1 | 176.80 (12) | C2—C1—C17—O3 | 114.72 (15) |
N1—C8—C9—C1 | −9.1 (2) | C9—C1—C17—O3 | −54.68 (18) |
C2—C1—C9—C8 | 178.55 (12) | C2—C1—C17—C11 | −64.85 (17) |
C17—C1—C9—C8 | −12.2 (2) | C9—C1—C17—C11 | 125.75 (14) |
Cg1 is the centroid of the C1–C4/C9/C10 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O5i | 0.93 | 2.44 | 3.137 (2) | 132 |
C18—H18C···O3i | 0.96 | 2.51 | 3.449 (2) | 167 |
C19—H19B···Cg1ii | 0.96 | 2.81 | 3.5845 (19) | 139 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H14ClNO5 |
Mr | 371.76 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 8.57511 (16), 14.0424 (3), 14.0842 (3) |
β (°) | 100.206 (1) |
V (Å3) | 1669.12 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.31 |
Crystal size (mm) | 0.60 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Numerical (NUMABS; Higashi, 1999) |
Tmin, Tmax | 0.294, 0.544 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29408, 3058, 2793 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.093, 1.03 |
No. of reflections | 3058 |
No. of parameters | 238 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.19 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP (Burnett & Johnson, 1996).
Cg1 is the centroid of the C1–C4/C9/C10 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O5i | 0.93 | 2.44 | 3.137 (2) | 132 |
C18—H18C···O3i | 0.96 | 2.51 | 3.449 (2) | 167 |
C19—H19B···Cg1ii | 0.96 | 2.81 | 3.5845 (19) | 139 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, −y+1, −z+1. |
Acknowledgements
The authors express their gratitude to Professor Keiichi Noguchi, Instumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by a Sasakawa Scientific Research Grant from the Japan Science Society.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene homologues exemplified by 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010). The aromatic rings in these molecules are arranged in a non-coplanar alignment to each other. Furthermore, we have also clarified the crystal structures of 1-monoaroylated naphthalene compounds. They have essentially the same non-coplanar structure with the 1,8-diaroylated naphthalene, e.g., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al., 2008), 2,7-dimethoxy-1-(4-nitrobenzoyl)naphthalene (Watanabe et al., 2010) and (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (Kato, et al., 2010). In the course of this work, we have revealed the crystal structure of 1-monoaroylnaphthalene compounds having a substituent, other than aroyl group, at the 8-position such as (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone (Mitsui, Nagasawa, Watanabe et al. 2010). The aroyl group and naphthalene ring in these molecules have similar configuration to 1,8-diaroylated naphthalene. As a part of our continuous study on the molecular structures of these kinds of homologous molecules, the crystal structure of title compound, a 1-chlorobenzoylated naphthalene bearing nitro group at the 8-position, is discussed in this report.
An ORTEP (Burnett & Johnson, 1996) plot of the title compound is displayed in Fig. 1. In the molecule, the dihedral angle between the benzene ring (C11—C16) and the naphthalene ring (C1—C10) is 70.62 (6)°. The nitro group are also twisted away from the naphthalene ring system, then the nitro group and the carbonyl group are arranged almost in parallel. The dihedral angle between the ketonic C=O plane (O3/C1/C11/C17) and naphthalene ring (C1—C10) is 60.33 (7)° [C9—C1—C17—O3 torsion angle is 54.68 (19)°] and between the nitro plane (O4/O5/N1/C8) and naphthalene ring (C1—C10) is 57.34 (8)° [O4—N1—C8—O9 torsion angle is 54.26 (18)°]. On the other hand, the carbonyl group and the 4-chlorophenyl one have almost coplanar configuration [C16—C11—C17—O3 torsion angle is 10.5 (2)°], but the torsion angle is larger than those of another homologous compounds, i.e., the torsion angles of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene and (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone are -4.4 (2)° and -3.6 (4)°, respectively.
The molecular packing of the title compound is mainly stabilized by weak intermolecular hydrogen bonds and van der Waals interactions. The 4-chlorophenyl groups interact with the nitro groups [C13—H13···O5 is 2.44 Å; (i) x, 3/2 - y, 1/2 + z] of adjacent molecules along the c axis (Fig. 2). Interaction between the methoxy groups and the carbonyl groups [C18—H18C···O3 = 2.51 Å; (i) x, 3/2 - y, 1/2 + z] form naphthalene ring systems into zigzag arrangement (Fig. 2). On the other hand, C—H···π interaction and π–π interactions deposit layer upon layer of naphthalene rings [C1/C2/C3/C4/C9/C10 ring with centroid Cg1 and C5-C10 ring with centroid Cg2 (Fig. 3). Furthermore, O4 and C11 interact with each other [O4···Cl1 = 2.9937 (12) Å; (iii) 2 - x, -y, 1-z] (Fig. 4).