organic compounds
(4-Chlorophenyl)(2-hydroxy-7-methoxynaphthalen-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, and bInstrumentation Analysis Center, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
*Correspondence e-mail: yonezawa@cc.tuat.ac.jp
The title compound, C18H13ClO3, has an intramolecular O—H⋯O=C hydrogen bond between the carbonyl group and the hydroxy substituent on the naphthalene ring system. The angle between the C=O bond plane and the naphthalene ring system is relatively small [20.96 (8)°]. The angle between the benzene ring and the carbonyl group is rather large [35.65 (9)°] compared to that in an analogous compound [3.43 (11)°] having a methoxy group instead of a hydroxy substituent.
Related literature
For the structures of closely related compounds, see: Nakaema et al. (2007, 2008); Mitsui et al. (2008).
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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808039603/su2069sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808039603/su2069Isup2.hkl
To a solution of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (33 mg, 0.10 mmol) in CH2Cl2 (1.0 ml) was added AlCl3 (67 mg, 0.50 mmol). The reaction mixture was refluxed for 30 min giving a dark red solution, which was then poured into H2O (5 ml) and CHCl3 (3 ml). The aqueous layer was extracted with CHCl3 (3 × 5 ml). The combined organic layers were washed with brine (3 × 10 ml), and dried over MgSO4 overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from hexane to give compound (II) as yellow platelets (m.p. 391–391.5 K, yield 23 mg, 75%).
Spectroscopic Data: 1H NMR (300 MHz, CDCl3) δ 11.35 (s, 1H), 7.85 (d, 1H), 7.63 (d, 1H), 7.58 (d, 2H), 7.40 (d, 2H), 7.07 (d, 1H), 6.91 (dd, 1H), 6.58 (d, 1H), 3.37 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 199.1, 162.6, 158.2, 138.8, 138.7, 136.5, 133.8, 130.7, 130.2, 128.9, 123.7, 116.4, 115.8, 113.4, 106.5, 54.5; IR (KBr): 3434, 1623, 1583, 1513, 1214, 843.
Anal. Calcd for C18H13ClO3: C 69.13, H 4.19. Found: C 69.11, H 4.09.
All the H-atoms could be located in difference Fourier maps. The OH hydrogen atom was freely refined: O2—H2 = 0.94 (2) Å. The C-bound H-atoms were subsequently refined as riding atoms, with C—H = 0.95 (aromatic) and 0.98 (methyl) Å, and Uiso(H) = 1.2Ueq(C).
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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C18H13ClO3 | Dx = 1.425 Mg m−3 |
Mr = 312.73 | Melting point = 391.0–391.5 K |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 42602 reflections |
a = 17.8030 (3) Å | θ = 3.4–68.2° |
b = 8.68121 (10) Å | µ = 2.41 mm−1 |
c = 18.8683 (3) Å | T = 123 K |
V = 2916.14 (8) Å3 | Plate, yellow |
Z = 8 | 0.60 × 0.15 × 0.05 mm |
F(000) = 1296 |
Rigaku R-AXIS RAPID diffractometer | 2669 independent reflections |
Radiation source: rotating anode | 2347 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 10.00 pixels mm-1 | θmax = 68.2°, θmin = 4.7° |
ω scans | h = −21→21 |
Absorption correction: numerical (NUMABS; Higashi, 1999) | k = −10→10 |
Tmin = 0.485, Tmax = 0.886 | l = −22→22 |
49864 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: dfimap |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0544P)2 + 0.6658P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2669 reflections | Δρmax = 0.17 e Å−3 |
205 parameters | Δρmin = −0.25 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: 0.00062 (11) |
C18H13ClO3 | V = 2916.14 (8) Å3 |
Mr = 312.73 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 17.8030 (3) Å | µ = 2.41 mm−1 |
b = 8.68121 (10) Å | T = 123 K |
c = 18.8683 (3) Å | 0.60 × 0.15 × 0.05 mm |
Rigaku R-AXIS RAPID diffractometer | 2669 independent reflections |
Absorption correction: numerical (NUMABS; Higashi, 1999) | 2347 reflections with I > 2σ(I) |
Tmin = 0.485, Tmax = 0.886 | Rint = 0.033 |
49864 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.17 e Å−3 |
2669 reflections | Δρmin = −0.25 e Å−3 |
205 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 | −0.05110 (2) | 0.23154 (6) | 0.500766 (19) | 0.05295 (17) | |
O1 | 0.04658 (5) | 0.08073 (14) | 0.17181 (6) | 0.0439 (3) | |
O2 | 0.12423 (7) | 0.21814 (15) | 0.07692 (6) | 0.0485 (3) | |
H2 | 0.0840 (13) | 0.163 (3) | 0.0974 (11) | 0.070 (7)* | |
O3 | 0.29872 (6) | 0.03670 (13) | 0.41875 (6) | 0.0474 (3) | |
C1 | 0.16824 (8) | 0.17285 (16) | 0.19660 (7) | 0.0299 (3) | |
C2 | 0.17846 (9) | 0.22425 (17) | 0.12659 (8) | 0.0373 (3) | |
C3 | 0.24694 (10) | 0.28979 (18) | 0.10428 (8) | 0.0432 (4) | |
H3 | 0.2518 | 0.3289 | 0.0575 | 0.052* | |
C4 | 0.30589 (9) | 0.29694 (18) | 0.14974 (9) | 0.0415 (4) | |
H4 | 0.3514 | 0.3439 | 0.1347 | 0.050* | |
C5 | 0.36473 (8) | 0.23357 (18) | 0.26380 (10) | 0.0419 (4) | |
H5 | 0.4104 | 0.2779 | 0.2476 | 0.050* | |
C6 | 0.36219 (8) | 0.16956 (18) | 0.32922 (9) | 0.0433 (4) | |
H6 | 0.4052 | 0.1714 | 0.3590 | 0.052* | |
C7 | 0.29510 (8) | 0.10024 (17) | 0.35260 (8) | 0.0368 (3) | |
C8 | 0.23210 (7) | 0.09796 (16) | 0.31021 (7) | 0.0312 (3) | |
H8 | 0.1880 | 0.0473 | 0.3262 | 0.037* | |
C9 | 0.23251 (7) | 0.17038 (15) | 0.24311 (7) | 0.0293 (3) | |
C10 | 0.30113 (7) | 0.23607 (16) | 0.21894 (9) | 0.0341 (3) | |
C11 | 0.09175 (7) | 0.12732 (16) | 0.21759 (8) | 0.0325 (3) | |
C12 | 0.06218 (7) | 0.14707 (16) | 0.29105 (8) | 0.0304 (3) | |
C13 | 0.00695 (8) | 0.04620 (17) | 0.31572 (8) | 0.0354 (3) | |
H13 | −0.0079 | −0.0389 | 0.2873 | 0.042* | |
C14 | −0.02637 (8) | 0.06910 (18) | 0.38113 (8) | 0.0389 (4) | |
H14 | −0.0630 | −0.0011 | 0.3984 | 0.047* | |
C15 | −0.00543 (8) | 0.19623 (18) | 0.42098 (8) | 0.0364 (3) | |
C16 | 0.04883 (8) | 0.29823 (17) | 0.39772 (8) | 0.0346 (3) | |
H16 | 0.0626 | 0.3846 | 0.4258 | 0.041* | |
C17 | 0.08296 (8) | 0.27253 (16) | 0.33264 (8) | 0.0320 (3) | |
H17 | 0.1208 | 0.3411 | 0.3163 | 0.038* | |
C18 | 0.23232 (12) | −0.0353 (2) | 0.44536 (9) | 0.0560 (5) | |
H18A | 0.2422 | −0.0770 | 0.4927 | 0.067* | |
H18B | 0.2174 | −0.1192 | 0.4135 | 0.067* | |
H18C | 0.1918 | 0.0407 | 0.4481 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0399 (3) | 0.0813 (4) | 0.0376 (2) | −0.0016 (2) | 0.00670 (15) | 0.00181 (19) |
O1 | 0.0292 (6) | 0.0561 (7) | 0.0463 (6) | −0.0002 (5) | −0.0077 (4) | −0.0137 (5) |
O2 | 0.0513 (7) | 0.0577 (8) | 0.0364 (6) | 0.0083 (6) | −0.0084 (5) | −0.0005 (5) |
O3 | 0.0542 (7) | 0.0414 (6) | 0.0466 (6) | 0.0105 (5) | −0.0200 (5) | −0.0052 (5) |
C1 | 0.0286 (7) | 0.0260 (7) | 0.0351 (7) | 0.0025 (5) | −0.0004 (5) | −0.0043 (5) |
C2 | 0.0416 (8) | 0.0317 (8) | 0.0385 (8) | 0.0069 (6) | −0.0016 (6) | −0.0048 (6) |
C3 | 0.0554 (9) | 0.0328 (9) | 0.0413 (8) | 0.0008 (7) | 0.0116 (8) | 0.0006 (7) |
C4 | 0.0395 (8) | 0.0313 (8) | 0.0536 (10) | −0.0038 (6) | 0.0153 (7) | −0.0075 (7) |
C5 | 0.0245 (7) | 0.0363 (8) | 0.0649 (10) | −0.0006 (6) | 0.0027 (7) | −0.0195 (7) |
C6 | 0.0268 (7) | 0.0396 (9) | 0.0635 (11) | 0.0073 (6) | −0.0130 (7) | −0.0200 (8) |
C7 | 0.0368 (8) | 0.0295 (8) | 0.0441 (8) | 0.0104 (6) | −0.0112 (6) | −0.0111 (6) |
C8 | 0.0274 (7) | 0.0263 (7) | 0.0398 (7) | 0.0028 (5) | −0.0033 (5) | −0.0053 (6) |
C9 | 0.0253 (7) | 0.0237 (7) | 0.0388 (7) | 0.0025 (5) | 0.0001 (5) | −0.0074 (5) |
C10 | 0.0276 (7) | 0.0267 (7) | 0.0482 (9) | 0.0006 (5) | 0.0051 (6) | −0.0102 (6) |
C11 | 0.0264 (7) | 0.0290 (7) | 0.0422 (8) | 0.0029 (6) | −0.0056 (6) | −0.0043 (6) |
C12 | 0.0213 (6) | 0.0298 (7) | 0.0402 (7) | 0.0025 (5) | −0.0033 (5) | −0.0007 (6) |
C13 | 0.0263 (7) | 0.0305 (8) | 0.0493 (8) | 0.0003 (6) | −0.0043 (6) | −0.0018 (6) |
C14 | 0.0274 (7) | 0.0392 (9) | 0.0502 (9) | −0.0027 (6) | −0.0010 (6) | 0.0097 (7) |
C15 | 0.0281 (7) | 0.0448 (9) | 0.0363 (7) | 0.0057 (6) | 0.0007 (6) | 0.0059 (6) |
C16 | 0.0312 (7) | 0.0342 (8) | 0.0383 (8) | 0.0026 (6) | −0.0017 (6) | −0.0028 (6) |
C17 | 0.0258 (7) | 0.0298 (7) | 0.0405 (8) | 0.0001 (5) | −0.0008 (6) | 0.0000 (6) |
C18 | 0.0896 (14) | 0.0381 (9) | 0.0402 (9) | −0.0063 (9) | −0.0156 (9) | 0.0008 (7) |
Cl1—C15 | 1.7381 (15) | C7—C8 | 1.3778 (19) |
O1—C11 | 1.2476 (17) | C8—C9 | 1.414 (2) |
O2—C2 | 1.3466 (19) | C8—H8 | 0.9500 |
O2—H2 | 0.94 (2) | C9—C10 | 1.4233 (19) |
O3—C7 | 1.3661 (19) | C11—C12 | 1.493 (2) |
O3—C18 | 1.429 (2) | C12—C17 | 1.392 (2) |
C1—C2 | 1.406 (2) | C12—C13 | 1.397 (2) |
C1—C9 | 1.4422 (19) | C13—C14 | 1.384 (2) |
C1—C11 | 1.4722 (19) | C13—H13 | 0.9500 |
C2—C3 | 1.410 (2) | C14—C15 | 1.387 (2) |
C3—C4 | 1.357 (2) | C14—H14 | 0.9500 |
C3—H3 | 0.9500 | C15—C16 | 1.382 (2) |
C4—C10 | 1.411 (2) | C16—C17 | 1.388 (2) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.354 (3) | C17—H17 | 0.9500 |
C5—C10 | 1.414 (2) | C18—H18A | 0.9800 |
C5—H5 | 0.9500 | C18—H18B | 0.9800 |
C6—C7 | 1.408 (2) | C18—H18C | 0.9800 |
C6—H6 | 0.9500 | ||
C2—O2—H2 | 106.3 (13) | C4—C10—C9 | 119.88 (14) |
C7—O3—C18 | 117.31 (12) | C5—C10—C9 | 119.30 (15) |
C2—C1—C9 | 118.28 (13) | O1—C11—C1 | 119.80 (13) |
C2—C1—C11 | 117.23 (13) | O1—C11—C12 | 116.93 (12) |
C9—C1—C11 | 124.48 (12) | C1—C11—C12 | 123.04 (12) |
O2—C2—C1 | 123.27 (15) | C17—C12—C13 | 119.32 (13) |
O2—C2—C3 | 115.35 (14) | C17—C12—C11 | 121.30 (13) |
C1—C2—C3 | 121.36 (14) | C13—C12—C11 | 119.07 (13) |
C4—C3—C2 | 119.91 (15) | C14—C13—C12 | 120.60 (14) |
C4—C3—H3 | 120.0 | C14—C13—H13 | 119.7 |
C2—C3—H3 | 120.0 | C12—C13—H13 | 119.7 |
C3—C4—C10 | 121.42 (14) | C13—C14—C15 | 118.87 (14) |
C3—C4—H4 | 119.3 | C13—C14—H14 | 120.6 |
C10—C4—H4 | 119.3 | C15—C14—H14 | 120.6 |
C6—C5—C10 | 121.68 (15) | C16—C15—C14 | 121.71 (14) |
C6—C5—H5 | 119.2 | C16—C15—Cl1 | 119.28 (12) |
C10—C5—H5 | 119.2 | C14—C15—Cl1 | 118.97 (12) |
C5—C6—C7 | 119.28 (14) | C15—C16—C17 | 118.95 (14) |
C5—C6—H6 | 120.4 | C15—C16—H16 | 120.5 |
C7—C6—H6 | 120.4 | C17—C16—H16 | 120.5 |
O3—C7—C8 | 124.26 (14) | C16—C17—C12 | 120.53 (13) |
O3—C7—C6 | 114.75 (13) | C16—C17—H17 | 119.7 |
C8—C7—C6 | 120.98 (15) | C12—C17—H17 | 119.7 |
C7—C8—C9 | 120.61 (13) | O3—C18—H18A | 109.5 |
C7—C8—H8 | 119.7 | O3—C18—H18B | 109.5 |
C9—C8—H8 | 119.7 | H18A—C18—H18B | 109.5 |
C8—C9—C10 | 118.02 (13) | O3—C18—H18C | 109.5 |
C8—C9—C1 | 123.19 (12) | H18A—C18—H18C | 109.5 |
C10—C9—C1 | 118.68 (13) | H18B—C18—H18C | 109.5 |
C4—C10—C5 | 120.77 (14) | ||
C9—C1—C2—O2 | 173.72 (13) | C6—C5—C10—C9 | 0.3 (2) |
C11—C1—C2—O2 | −7.2 (2) | C8—C9—C10—C4 | 174.23 (12) |
C9—C1—C2—C3 | −7.8 (2) | C1—C9—C10—C4 | −2.23 (19) |
C11—C1—C2—C3 | 171.28 (13) | C8—C9—C10—C5 | −3.14 (19) |
O2—C2—C3—C4 | −177.98 (14) | C1—C9—C10—C5 | −179.59 (12) |
C1—C2—C3—C4 | 3.4 (2) | C2—C1—C11—O1 | 26.3 (2) |
C2—C3—C4—C10 | 1.8 (2) | C9—C1—C11—O1 | −154.68 (14) |
C10—C5—C6—C7 | 1.6 (2) | C2—C1—C11—C12 | −148.00 (14) |
C18—O3—C7—C8 | −0.5 (2) | C9—C1—C11—C12 | 31.0 (2) |
C18—O3—C7—C6 | 179.99 (13) | O1—C11—C12—C17 | −139.55 (14) |
C5—C6—C7—O3 | 178.89 (13) | C1—C11—C12—C17 | 34.9 (2) |
C5—C6—C7—C8 | −0.6 (2) | O1—C11—C12—C13 | 33.95 (19) |
O3—C7—C8—C9 | 178.21 (12) | C1—C11—C12—C13 | −151.57 (13) |
C6—C7—C8—C9 | −2.4 (2) | C17—C12—C13—C14 | −0.7 (2) |
C7—C8—C9—C10 | 4.17 (19) | C11—C12—C13—C14 | −174.37 (13) |
C7—C8—C9—C1 | −179.55 (13) | C12—C13—C14—C15 | 1.7 (2) |
C2—C1—C9—C8 | −169.18 (13) | C13—C14—C15—C16 | −1.4 (2) |
C11—C1—C9—C8 | 11.8 (2) | C13—C14—C15—Cl1 | 176.26 (11) |
C2—C1—C9—C10 | 7.07 (19) | C14—C15—C16—C17 | 0.2 (2) |
C11—C1—C9—C10 | −171.92 (13) | Cl1—C15—C16—C17 | −177.50 (11) |
C3—C4—C10—C5 | 175.05 (14) | C15—C16—C17—C12 | 0.8 (2) |
C3—C4—C10—C9 | −2.3 (2) | C13—C12—C17—C16 | −0.5 (2) |
C6—C5—C10—C4 | −177.05 (14) | C11—C12—C17—C16 | 172.96 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.94 (2) | 1.71 (2) | 2.5573 (16) | 148 (2) |
Experimental details
Crystal data | |
Chemical formula | C18H13ClO3 |
Mr | 312.73 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 123 |
a, b, c (Å) | 17.8030 (3), 8.68121 (10), 18.8683 (3) |
V (Å3) | 2916.14 (8) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 2.41 |
Crystal size (mm) | 0.60 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Numerical (NUMABS; Higashi, 1999) |
Tmin, Tmax | 0.485, 0.886 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 49864, 2669, 2347 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.096, 1.08 |
No. of reflections | 2669 |
No. of parameters | 205 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.25 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.94 (2) | 1.71 (2) | 2.5573 (16) | 148 (2) |
Acknowledgements
This work was financially supported by SEIKI KOGYO CO., Ltd, Tokorozawa, Saitama, Japan.
References
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
Recently, we have reported on the crystal structure of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene, (I) [Mitsui et al., 2008]. As a part of our ongoing studies on the synthesis and crystal structure analyses of aroylated naphthalene derivatives, we prepared and analysed the crystal structure of the title compound, (II). Compound (II) was prepared by regioselective demethylation reaction of compound (I) with aluminium trichloride.
The molecular structure of compound (II) is illustrated in Fig. 1. In analogous aroylated naphthalenes, for example compound (I) shown in Fig. 2, the C═O bond plane is almost perpendicular to the mean plane of the naphthalene ring (Nakaema et al., 2007, 2008; Mitsui et al., 2008). In contrast, the angle between the C═O bond and the naphthalene ring in compound (II) is considerably smaller, i.e. 20.96 (8)°. This is apparently caused by the intramolecular O—H···O═C hydrogen bond, which forms a six-membered ring including the carbonyl group and an edge of the naphthalene ring (Fig. 1 and Table 1).
In compound (I) the C═O bond and the benzene ring are almost coplanar with a dihedral angle of 3.43 (11)°. In compound (II) the mean plane of the benzene ring is twisted away from the C═O bond by 35.65 (9)°. This is presumably caused by the release of the rather large steric repulsion between the benzene ring and the naphthalene ring brought about by the small angle of the C═O bond plane and the naphthalene ring. The dihedral angle between the naphthalene ring (C1—C10) and the benzene ring (C12—C17) is 58.10 (6)°.
In the crystal structure the molecular packing of (II) is mainly stabilized by van der Waals interactions. The naphthalene rings interact with the phenyl rings [C5···C13 = 3.363 (2) Å] and the carbonyl groups [H6···O1 = 2.70 Å] along the a-axis. They also interact with the methyl groups [H3···C18 = 2.79 Å] and aroyl groups [H6···Cl1 = 2.88 Å] along the c-axis (Fig. 3). On the other hand, the naphthalene rings also interact with the methyl groups [C6···H18B = 2.81 Å, C7···H18B = 2.70 Å] and the phenyl rings [C6···H17 = 2.88 Å, C7···H17 = 2.79 Å] along the b-axis. The naphthalene rings are almost perpendicular to the phenyl rings of the adjacent molecules along the b-axis. In addition, the hydroxy groups interact with the phenyl rings [O2···H14 = 2.71 Å] along the b-axis (Fig. 4).