Literature DB >> 21201947

2-(4-Chloro-benzo-yl)-3,6-dimethoxy-naphthalene.

Kosuke Nakaema, Akiko Okamoto, Masahiro Imaizumi, Keiichi Noguchi, Noriyuki Yonezawa.   

Abstract

In the title compound, C(19)H(15)ClO(3), the inter-planar angle between the naphthalene and benzene ring systems is 62.67 (6)°. The carbonyl group is twisted from both ring planes, with torsion angles of -44.9 (2)° with respect to the naphthalene ring and -26.7 (2)° with respect to the phenyl-ene ring. There is an inter-molecular hydrogen bond between an H atom of one meth-oxy group and the O atom of the second meth-oxy group, forming chains along the ac diagonal.

Entities:  

Year:  2008        PMID： 21201947      PMCID： PMC2960802          DOI： 10.1107/S1600536808004704

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Ahn et al. (2003 ▶); Allen et al. (1998 ▶); Chen et al. (2005 ▶); Crasto & Stevens (1998 ▶, 2002 ▶); Lorenzetti et al. (2005 ▶); Nakaema et al. (2007 ▶); Su et al. (2004 ▶); Wang & Guen (1995 ▶).

Experimental

Crystal data

C19H15ClO3 M = 326.76 Monoclinic, a = 8.1894 (5) Å b = 20.5251 (13) Å c = 9.9098 (7) Å β = 106.358 (4)° V = 1598.29 (18) Å3 Z = 4 Cu Kα radiation μ = 2.22 mm−1 T = 296 K 0.50 × 0.25 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.458, T max = 0.801 30087 measured reflections 2917 independent reflections 2652 reflections with I > 2σ(I) R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.100 S = 1.07 2917 reflections 211 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.28 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: SIR92 (Altomare et al., 1994 ▶); 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 I, global. DOI: 10.1107/S1600536808004704/fl2189sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004704/fl2189Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H15ClO3F000 = 680
Mr = 326.76Dx = 1.358 Mg m−3
Monoclinic, P21/cMelting point = 424.8–425.2 K
Hall symbol: -P 2ybcCu Kα radiation λ = 1.54187 Å
a = 8.1894 (5) ÅCell parameters from 28831 reflections
b = 20.5251 (13) Åθ = 4.3–68.2º
c = 9.9098 (7) ŵ = 2.22 mm−1
β = 106.358 (4)ºT = 296 K
V = 1598.29 (18) Å3Platelet, colorless
Z = 40.50 × 0.25 × 0.10 mm
Rigaku R-AXIS RAPID diffractometer2917 independent reflections
Radiation source: rotating anode2652 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
Detector resolution: 10.00 pixels mm-1θmax = 68.2º
T = 296 Kθmin = 4.3º
ω scansh = −9→9
Absorption correction: numerical(NUMABS; Higashi, 1999)k = −24→24
Tmin = 0.458, Tmax = 0.801l = −11→11
30087 measured reflections
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033  w = 1/[σ2(Fo2) + (0.054P)2 + 0.2906P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.17 e Å−3
2917 reflectionsΔρmin = −0.27 e Å−3
211 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (4)
Secondary atom site location: difference Fourier map
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.
xyzUiso*/Ueq
Cl1−0.25848 (6)0.44273 (2)−0.48382 (4)0.06829 (17)
O1−0.25367 (15)0.47599 (6)0.18888 (12)0.0662 (3)
O2−0.21482 (13)0.30244 (5)0.06521 (11)0.0560 (3)
O30.44684 (14)0.21975 (6)0.70829 (12)0.0662 (3)
C10.01126 (17)0.27069 (7)0.26978 (14)0.0452 (3)
H10.00240.22720.24210.054*
C2−0.09091 (17)0.31627 (7)0.18563 (14)0.0439 (3)
C3−0.07602 (17)0.38337 (7)0.22433 (14)0.0441 (3)
C40.03617 (18)0.40089 (7)0.35010 (15)0.0478 (3)
H40.04300.44440.37700.057*
C50.14146 (17)0.35510 (7)0.44000 (14)0.0457 (3)
C60.2559 (2)0.37226 (8)0.57153 (17)0.0573 (4)
H60.26420.41550.60060.069*
C70.3536 (2)0.32631 (8)0.65574 (17)0.0602 (4)
H70.42800.33840.74160.072*
C80.34269 (17)0.26071 (8)0.61388 (15)0.0515 (4)
C90.23401 (16)0.24175 (7)0.48760 (15)0.0475 (3)
H90.22840.19820.46060.057*
C100.13031 (16)0.28874 (7)0.39836 (14)0.0427 (3)
C11−0.18305 (18)0.43524 (7)0.13539 (15)0.0474 (3)
C12−0.19823 (17)0.43754 (6)−0.01795 (15)0.0446 (3)
C13−0.34026 (19)0.46603 (8)−0.11003 (16)0.0559 (4)
H13−0.42420.4839−0.07470.067*
C14−0.3593 (2)0.46831 (8)−0.25247 (17)0.0579 (4)
H14−0.45560.4870−0.31320.070*
C15−0.2335 (2)0.44241 (6)−0.30339 (15)0.0498 (3)
C16−0.0880 (2)0.41601 (8)−0.21476 (16)0.0561 (4)
H16−0.00170.4004−0.25020.067*
C17−0.07217 (19)0.41313 (7)−0.07204 (16)0.0527 (4)
H170.02460.3945−0.01160.063*
C18−0.2507 (2)0.23549 (8)0.03027 (17)0.0576 (4)
H18A−0.28030.21400.10610.086*
H18B−0.15190.21510.01490.086*
H18C−0.34390.2324−0.05370.086*
C190.4318 (2)0.15190 (9)0.6806 (2)0.0759 (5)
H19A0.45730.14290.59360.114*
H19B0.31780.13810.67380.114*
H19C0.51020.12880.75560.114*
U11U22U33U12U13U23
Cl10.1005 (4)0.0595 (3)0.0412 (2)0.0008 (2)0.0139 (2)0.00090 (15)
O10.0758 (7)0.0705 (7)0.0523 (6)0.0258 (6)0.0178 (5)0.0004 (5)
O20.0605 (6)0.0511 (6)0.0437 (5)−0.0009 (5)−0.0059 (5)0.0007 (4)
O30.0597 (6)0.0702 (7)0.0541 (7)0.0035 (5)−0.0078 (5)0.0142 (5)
C10.0489 (7)0.0428 (7)0.0405 (7)−0.0011 (5)0.0070 (6)−0.0004 (5)
C20.0440 (7)0.0491 (7)0.0355 (7)−0.0019 (5)0.0063 (5)0.0004 (5)
C30.0458 (7)0.0467 (7)0.0385 (7)0.0014 (5)0.0099 (6)0.0039 (5)
C40.0523 (8)0.0437 (7)0.0454 (8)−0.0030 (6)0.0105 (6)0.0002 (6)
C50.0450 (7)0.0489 (7)0.0407 (7)−0.0052 (6)0.0079 (6)0.0018 (6)
C60.0609 (9)0.0543 (8)0.0480 (8)−0.0101 (7)0.0014 (7)−0.0023 (7)
C70.0586 (9)0.0664 (10)0.0442 (8)−0.0109 (7)−0.0039 (7)0.0006 (7)
C80.0436 (7)0.0621 (9)0.0439 (8)−0.0021 (6)0.0044 (6)0.0109 (6)
C90.0458 (7)0.0495 (8)0.0442 (8)−0.0006 (6)0.0077 (6)0.0047 (6)
C100.0401 (6)0.0487 (7)0.0381 (7)−0.0029 (5)0.0090 (5)0.0035 (5)
C110.0468 (7)0.0472 (7)0.0467 (8)0.0045 (6)0.0106 (6)0.0016 (6)
C120.0474 (7)0.0405 (7)0.0443 (8)0.0040 (5)0.0101 (6)0.0039 (5)
C130.0526 (8)0.0628 (9)0.0504 (9)0.0167 (7)0.0117 (7)0.0064 (7)
C140.0561 (8)0.0608 (9)0.0497 (9)0.0109 (7)0.0033 (7)0.0088 (7)
C150.0652 (9)0.0395 (7)0.0417 (8)−0.0021 (6)0.0102 (6)0.0031 (5)
C160.0638 (9)0.0562 (8)0.0516 (9)0.0124 (7)0.0218 (7)0.0063 (7)
C170.0501 (7)0.0569 (8)0.0491 (8)0.0138 (6)0.0109 (6)0.0100 (7)
C180.0579 (9)0.0551 (9)0.0509 (9)−0.0030 (7)0.0007 (7)−0.0085 (7)
C190.0724 (11)0.0675 (11)0.0721 (12)0.0099 (9)−0.0050 (9)0.0169 (9)
Cl1—C151.7415 (15)C8—C91.372 (2)
O1—C111.2196 (18)C9—C101.4180 (19)
O2—C21.3610 (16)C9—H90.9300
O2—C181.4273 (18)C11—C121.490 (2)
O3—C81.3638 (17)C12—C171.384 (2)
O3—C191.418 (2)C12—C131.3891 (19)
C1—C21.3703 (19)C13—C141.377 (2)
C1—C101.4184 (18)C13—H130.9300
C1—H10.9300C14—C151.376 (2)
C2—C31.425 (2)C14—H140.9300
C3—C41.3718 (19)C15—C161.377 (2)
C3—C111.4980 (18)C16—C171.385 (2)
C4—C51.4098 (19)C16—H160.9300
C4—H40.9300C17—H170.9300
C5—C101.419 (2)C18—H18A0.9600
C5—C61.419 (2)C18—H18B0.9600
C6—C71.360 (2)C18—H18C0.9600
C6—H60.9300C19—H19A0.9600
C7—C81.404 (2)C19—H19B0.9600
C7—H70.9300C19—H19C0.9600
C2—O2—C18117.72 (11)O1—C11—C3120.14 (13)
C8—O3—C19117.97 (13)C12—C11—C3119.31 (12)
C2—C1—C10121.05 (13)C17—C12—C13118.41 (13)
C2—C1—H1119.5C17—C12—C11121.76 (12)
C10—C1—H1119.5C13—C12—C11119.81 (13)
O2—C2—C1124.60 (12)C14—C13—C12121.32 (14)
O2—C2—C3115.07 (11)C14—C13—H13119.3
C1—C2—C3120.30 (12)C12—C13—H13119.3
C4—C3—C2118.85 (12)C15—C14—C13118.88 (14)
C4—C3—C11118.65 (13)C15—C14—H14120.6
C2—C3—C11122.47 (12)C13—C14—H14120.6
C3—C4—C5122.22 (13)C14—C15—C16121.41 (14)
C3—C4—H4118.9C14—C15—Cl1119.44 (12)
C5—C4—H4118.9C16—C15—Cl1119.15 (12)
C4—C5—C10118.58 (12)C15—C16—C17118.92 (14)
C4—C5—C6122.91 (13)C15—C16—H16120.5
C10—C5—C6118.50 (13)C17—C16—H16120.5
C7—C6—C5120.92 (15)C12—C17—C16120.98 (13)
C7—C6—H6119.5C12—C17—H17119.5
C5—C6—H6119.5C16—C17—H17119.5
C6—C7—C8120.41 (14)O2—C18—H18A109.5
C6—C7—H7119.8O2—C18—H18B109.5
C8—C7—H7119.8H18A—C18—H18B109.5
O3—C8—C9124.79 (15)O2—C18—H18C109.5
O3—C8—C7114.39 (13)H18A—C18—H18C109.5
C9—C8—C7120.82 (13)H18B—C18—H18C109.5
C8—C9—C10119.77 (14)O3—C19—H19A109.5
C8—C9—H9120.1O3—C19—H19B109.5
C10—C9—H9120.1H19A—C19—H19B109.5
C9—C10—C1121.47 (13)O3—C19—H19C109.5
C9—C10—C5119.58 (12)H19A—C19—H19C109.5
C1—C10—C5118.93 (12)H19B—C19—H19C109.5
O1—C11—C12120.53 (13)
C18—O2—C2—C15.6 (2)C2—C1—C10—C50.6 (2)
C18—O2—C2—C3−172.22 (13)C4—C5—C10—C9−179.51 (12)
C10—C1—C2—O2−175.97 (12)C6—C5—C10—C9−0.7 (2)
C10—C1—C2—C31.7 (2)C4—C5—C10—C1−1.44 (19)
O2—C2—C3—C4174.76 (12)C6—C5—C10—C1177.42 (13)
C1—C2—C3—C4−3.1 (2)C4—C3—C11—O1−44.9 (2)
O2—C2—C3—C11−2.86 (19)C2—C3—C11—O1132.68 (15)
C1—C2—C3—C11179.26 (13)C4—C3—C11—C12133.39 (14)
C2—C3—C4—C52.3 (2)C2—C3—C11—C12−48.98 (19)
C11—C3—C4—C5179.99 (13)O1—C11—C12—C17151.86 (15)
C3—C4—C5—C100.0 (2)C3—C11—C12—C17−26.5 (2)
C3—C4—C5—C6−178.83 (14)O1—C11—C12—C13−26.7 (2)
C4—C5—C6—C7179.15 (15)C3—C11—C12—C13154.93 (14)
C10—C5—C6—C70.3 (2)C17—C12—C13—C142.1 (2)
C5—C6—C7—C8−0.1 (3)C11—C12—C13—C14−179.24 (14)
C19—O3—C8—C9−5.8 (2)C12—C13—C14—C15−0.8 (3)
C19—O3—C8—C7173.98 (16)C13—C14—C15—C16−1.7 (2)
C6—C7—C8—O3−179.71 (15)C13—C14—C15—Cl1178.11 (13)
C6—C7—C8—C90.1 (2)C14—C15—C16—C172.8 (2)
O3—C8—C9—C10179.38 (13)Cl1—C15—C16—C17−177.04 (12)
C7—C8—C9—C10−0.4 (2)C13—C12—C17—C16−1.0 (2)
C8—C9—C10—C1−177.32 (13)C11—C12—C17—C16−179.62 (14)
C8—C9—C10—C50.7 (2)C15—C16—C17—C12−1.4 (2)
C2—C1—C10—C9178.63 (13)
D—H···AD—HH···AD···AD—H···A
C18—H18C···O3i0.962.513.460 (2)171
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C18—H18C⋯O3i0.962.513.460 (2)171

Symmetry code: (i) .

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1.  (3,6-Dimeth-oxy-2-naphth-yl)(4-fluoro-benzo-yl)methanone.

Authors:  Shoji Watanabe; Toyokazu Muto; Atsushi Nagasawa; Akiko Okamoto; Noriyuki Yonezawa
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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-19

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