Literature DB >> 22065715

(2-Benzoyl-phen-yl)(2-meth-oxy-1-naphth-yl)methanone.

G Jagadeesan, K Sethusankar, R Sivasakthikumaran, Arasambattu K Mohanakrishnan.   

Abstract

In the title compound C(25)H(18)O(3), the central benzene ring forms dihedral angles of 87.4 (5) and 85.4 (4)° with the phenyl ring and the naphthalene ring system, respectively. The carbonyl O atoms deviate significantly from the phenyl ring and the meth-oxy-substituted naphthalene ring system [by 0.508 (1) and 0.821 (1) Å, respectively]. The crystal packing is stabilized by C-H⋯O hydrogen bonds, which generate C(6) chains, and C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID： 22065715      PMCID： PMC3201367          DOI： 10.1107/S1600536811038049

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


Related literature

For chelating reagents of metallic systems, see: Liang et al. (2003 ▶). For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶). For related structures, see: Tsumuki et al. (2011 ▶); Jagadeesan et al. (2011 ▶).

Experimental

Crystal data

C25H18O3 M = 366.39 Monoclinic, a = 15.0592 (7) Å b = 7.6768 (3) Å c = 16.9274 (8) Å β = 106.137 (2)° V = 1879.81 (15) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 295 K 0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEX II CCD diffractometer 22918 measured reflections 5339 independent reflections 3546 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.142 S = 1.00 5339 reflections 254 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038049/rk2301sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038049/rk2301Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811038049/rk2301Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H18O3F(000) = 768
Mr = 366.39Dx = 1.295 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3546 reflections
a = 15.0592 (7) Åθ = 1.4–29.8°
b = 7.6768 (3) ŵ = 0.08 mm−1
c = 16.9274 (8) ÅT = 295 K
β = 106.137 (2)°Block, colourless
V = 1879.81 (15) Å30.30 × 0.25 × 0.20 mm
Z = 4
Bruker Kappa APEX II CCD diffractometer3546 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 29.8°, θmin = 2.5°
φ– and ω–scansh = −21→20
22918 measured reflectionsk = −7→10
5339 independent reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0646P)2 + 0.4893P] where P = (Fo2 + 2Fc2)/3
5339 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C10.32655 (11)0.5102 (2)0.64285 (10)0.0489 (4)
H10.28150.58940.61590.059*
C20.33289 (13)0.4623 (3)0.72296 (11)0.0645 (5)
H20.29150.50750.74940.077*
C30.40028 (15)0.3480 (3)0.76349 (12)0.0694 (5)
H30.40440.31550.81730.083*
C40.46149 (16)0.2816 (3)0.72472 (12)0.0716 (6)
H40.50760.20570.75280.086*
C50.45535 (12)0.3264 (2)0.64411 (10)0.0537 (4)
H50.49690.28020.61810.064*
C60.38683 (9)0.44093 (17)0.60238 (9)0.0383 (3)
C70.37750 (8)0.48647 (16)0.51530 (8)0.0339 (3)
C80.33986 (8)0.66384 (16)0.48624 (8)0.0315 (3)
C90.39631 (10)0.80583 (18)0.51630 (9)0.0407 (3)
H90.45180.78930.55670.049*
C100.37067 (11)0.97165 (19)0.48663 (10)0.0456 (3)
H100.40911.06560.50710.055*
C110.28879 (11)0.99841 (18)0.42712 (10)0.0452 (3)
H110.27191.11010.40730.054*
C120.23162 (10)0.85857 (17)0.39690 (9)0.0390 (3)
H120.17630.87670.35650.047*
C130.25602 (8)0.69061 (15)0.42638 (8)0.0308 (3)
C140.18976 (8)0.54380 (17)0.39884 (8)0.0329 (3)
C150.11451 (9)0.57010 (17)0.32057 (8)0.0353 (3)
C160.13622 (10)0.57056 (18)0.24428 (9)0.0402 (3)
C170.22628 (12)0.5324 (2)0.23795 (11)0.0529 (4)
H170.27350.50740.28520.063*
C180.24417 (16)0.5322 (3)0.16352 (13)0.0714 (5)
H180.30330.50530.16030.086*
C190.1752 (2)0.5716 (3)0.09233 (13)0.0819 (7)
H190.18880.57270.04200.098*
C200.08820 (18)0.6083 (3)0.09543 (11)0.0717 (6)
H200.04290.63480.04710.086*
C210.06502 (12)0.6069 (2)0.17118 (9)0.0492 (4)
C22−0.02422 (13)0.6403 (2)0.17769 (11)0.0572 (5)
H22−0.07100.66620.13030.069*
C23−0.04461 (11)0.6362 (2)0.25055 (11)0.0533 (4)
H23−0.10480.65710.25260.064*
C240.02565 (9)0.60013 (19)0.32376 (9)0.0417 (3)
C25−0.08045 (13)0.6050 (3)0.40589 (14)0.0703 (5)
H25A−0.10930.71200.38280.105*
H25B−0.07970.59810.46270.105*
H25C−0.11460.50830.37640.105*
O10.40464 (7)0.39130 (13)0.46951 (6)0.0455 (3)
O20.19662 (7)0.41118 (13)0.43910 (7)0.0480 (3)
O30.01160 (7)0.60000 (18)0.39966 (7)0.0601 (3)
U11U22U33U12U13U23
C10.0412 (8)0.0565 (9)0.0468 (9)0.0060 (7)0.0086 (6)0.0080 (7)
C20.0571 (11)0.0871 (14)0.0491 (10)0.0011 (10)0.0148 (8)0.0082 (9)
C30.0752 (13)0.0791 (13)0.0457 (10)−0.0029 (11)0.0034 (9)0.0149 (9)
C40.0811 (14)0.0612 (11)0.0543 (11)0.0194 (10)−0.0114 (10)0.0121 (9)
C50.0537 (9)0.0470 (9)0.0500 (9)0.0148 (7)−0.0029 (7)0.0000 (7)
C60.0346 (7)0.0327 (6)0.0415 (7)−0.0008 (5)0.0004 (5)0.0008 (5)
C70.0245 (6)0.0307 (6)0.0424 (7)−0.0018 (5)0.0023 (5)−0.0020 (5)
C80.0296 (6)0.0302 (6)0.0345 (6)−0.0002 (5)0.0087 (5)−0.0015 (5)
C90.0352 (7)0.0374 (7)0.0455 (8)−0.0046 (5)0.0043 (6)−0.0055 (6)
C100.0493 (8)0.0324 (7)0.0544 (9)−0.0093 (6)0.0132 (7)−0.0070 (6)
C110.0584 (9)0.0273 (6)0.0512 (9)0.0015 (6)0.0172 (7)0.0035 (6)
C120.0416 (7)0.0351 (7)0.0373 (7)0.0042 (5)0.0058 (6)0.0040 (5)
C130.0312 (6)0.0292 (6)0.0311 (6)0.0004 (5)0.0069 (5)−0.0008 (5)
C140.0278 (6)0.0347 (6)0.0345 (7)0.0002 (5)0.0058 (5)0.0010 (5)
C150.0315 (6)0.0334 (6)0.0357 (7)−0.0017 (5)0.0005 (5)0.0007 (5)
C160.0460 (8)0.0334 (7)0.0373 (7)−0.0054 (6)0.0053 (6)−0.0002 (5)
C170.0548 (9)0.0566 (9)0.0504 (9)−0.0036 (8)0.0199 (7)−0.0007 (7)
C180.0841 (14)0.0756 (13)0.0664 (13)−0.0067 (11)0.0404 (11)−0.0011 (10)
C190.119 (2)0.0822 (15)0.0550 (12)−0.0156 (14)0.0412 (13)−0.0003 (10)
C200.1073 (17)0.0608 (11)0.0361 (9)−0.0140 (11)0.0019 (10)0.0057 (8)
C210.0609 (10)0.0378 (7)0.0388 (8)−0.0070 (7)−0.0028 (7)0.0028 (6)
C220.0588 (10)0.0436 (8)0.0500 (10)−0.0019 (7)−0.0167 (8)0.0052 (7)
C230.0327 (7)0.0482 (9)0.0669 (11)0.0017 (6)−0.0063 (7)0.0003 (7)
C240.0334 (7)0.0407 (7)0.0460 (8)−0.0009 (6)0.0027 (6)−0.0014 (6)
C250.0454 (10)0.0783 (13)0.0950 (15)0.0089 (9)0.0326 (10)0.0045 (11)
O10.0449 (6)0.0386 (5)0.0523 (6)0.0062 (4)0.0124 (5)−0.0055 (4)
O20.0410 (6)0.0397 (5)0.0546 (6)−0.0075 (4)−0.0011 (5)0.0132 (5)
O30.0362 (6)0.0881 (9)0.0573 (7)0.0048 (6)0.0153 (5)−0.0010 (6)
C1—C21.382 (2)C14—O21.2135 (16)
C1—C61.386 (2)C14—C151.4986 (17)
C1—H10.9300C15—C241.3737 (19)
C2—C31.373 (3)C15—C161.417 (2)
C2—H20.9300C16—C171.420 (2)
C3—C41.370 (3)C16—C211.422 (2)
C3—H30.9300C17—C181.360 (2)
C4—C51.385 (3)C17—H170.9300
C4—H40.9300C18—C191.388 (3)
C5—C61.390 (2)C18—H180.9300
C5—H50.9300C19—C201.355 (3)
C6—C71.483 (2)C19—H190.9300
C7—O11.2156 (16)C20—C211.419 (3)
C7—C81.5041 (17)C20—H200.9300
C8—C91.3891 (18)C21—C221.402 (3)
C8—C131.3971 (18)C22—C231.352 (3)
C9—C101.383 (2)C22—H220.9300
C9—H90.9300C23—C241.415 (2)
C10—C111.374 (2)C23—H230.9300
C10—H100.9300C24—O31.3589 (19)
C11—C121.382 (2)C25—O31.420 (2)
C11—H110.9300C25—H25A0.9600
C12—C131.3945 (17)C25—H25B0.9600
C12—H120.9300C25—H25C0.9600
C13—C141.4915 (17)
C2—C1—C6120.42 (15)O2—C14—C15122.34 (11)
C2—C1—H1119.8C13—C14—C15116.77 (11)
C6—C1—H1119.8C24—C15—C16120.62 (12)
C3—C2—C1120.02 (18)C24—C15—C14119.56 (12)
C3—C2—H2120.0C16—C15—C14119.78 (12)
C1—C2—H2120.0C15—C16—C17122.35 (13)
C4—C3—C2120.05 (18)C15—C16—C21118.97 (14)
C4—C3—H3120.0C17—C16—C21118.66 (14)
C2—C3—H3120.0C18—C17—C16120.63 (17)
C3—C4—C5120.67 (17)C18—C17—H17119.7
C3—C4—H4119.7C16—C17—H17119.7
C5—C4—H4119.7C17—C18—C19120.7 (2)
C4—C5—C6119.65 (17)C17—C18—H18119.6
C4—C5—H5120.2C19—C18—H18119.6
C6—C5—H5120.2C20—C19—C18120.66 (19)
C1—C6—C5119.15 (14)C20—C19—H19119.7
C1—C6—C7120.43 (12)C18—C19—H19119.7
C5—C6—C7120.41 (13)C19—C20—C21121.09 (18)
O1—C7—C6122.44 (12)C19—C20—H20119.5
O1—C7—C8119.89 (12)C21—C20—H20119.5
C6—C7—C8117.48 (11)C22—C21—C20123.45 (16)
C9—C8—C13119.21 (12)C22—C21—C16118.35 (15)
C9—C8—C7117.00 (11)C20—C21—C16118.19 (18)
C13—C8—C7123.56 (11)C23—C22—C21122.22 (14)
C10—C9—C8120.56 (13)C23—C22—H22118.9
C10—C9—H9119.7C21—C22—H22118.9
C8—C9—H9119.7C22—C23—C24119.96 (15)
C11—C10—C9120.46 (13)C22—C23—H23120.0
C11—C10—H10119.8C24—C23—H23120.0
C9—C10—H10119.8O3—C24—C15116.51 (12)
C10—C11—C12119.67 (13)O3—C24—C23123.58 (14)
C10—C11—H11120.2C15—C24—C23119.86 (15)
C12—C11—H11120.2O3—C25—H25A109.5
C11—C12—C13120.70 (13)O3—C25—H25B109.5
C11—C12—H12119.6H25A—C25—H25B109.5
C13—C12—H12119.6O3—C25—H25C109.5
C12—C13—C8119.39 (11)H25A—C25—H25C109.5
C12—C13—C14120.00 (11)H25B—C25—H25C109.5
C8—C13—C14120.45 (11)C24—O3—C25118.82 (14)
O2—C14—C13120.88 (11)
C6—C1—C2—C31.2 (3)O2—C14—C15—C2473.13 (18)
C1—C2—C3—C40.2 (3)C13—C14—C15—C24−105.93 (14)
C2—C3—C4—C5−1.1 (3)O2—C14—C15—C16−109.33 (16)
C3—C4—C5—C60.5 (3)C13—C14—C15—C1671.61 (16)
C2—C1—C6—C5−1.8 (2)C24—C15—C16—C17−177.12 (14)
C2—C1—C6—C7177.37 (15)C14—C15—C16—C175.4 (2)
C4—C5—C6—C10.9 (2)C24—C15—C16—C211.5 (2)
C4—C5—C6—C7−178.24 (15)C14—C15—C16—C21−175.97 (12)
C1—C6—C7—O1−154.41 (14)C15—C16—C17—C18179.22 (16)
C5—C6—C7—O124.7 (2)C21—C16—C17—C180.6 (2)
C1—C6—C7—C830.61 (18)C16—C17—C18—C190.9 (3)
C5—C6—C7—C8−150.25 (13)C17—C18—C19—C20−1.1 (3)
O1—C7—C8—C9−104.93 (15)C18—C19—C20—C21−0.3 (3)
C6—C7—C8—C970.18 (16)C19—C20—C21—C22−178.64 (18)
O1—C7—C8—C1369.48 (17)C19—C20—C21—C161.7 (3)
C6—C7—C8—C13−115.41 (14)C15—C16—C21—C22−0.2 (2)
C13—C8—C9—C10−0.9 (2)C17—C16—C21—C22178.51 (14)
C7—C8—C9—C10173.74 (13)C15—C16—C21—C20179.46 (14)
C8—C9—C10—C110.2 (2)C17—C16—C21—C20−1.8 (2)
C9—C10—C11—C120.1 (2)C20—C21—C22—C23179.24 (16)
C10—C11—C12—C130.2 (2)C16—C21—C22—C23−1.1 (2)
C11—C12—C13—C8−0.9 (2)C21—C22—C23—C241.1 (2)
C11—C12—C13—C14174.35 (13)C16—C15—C24—O3−178.97 (12)
C9—C8—C13—C121.28 (19)C14—C15—C24—O3−1.45 (19)
C7—C8—C13—C12−173.02 (12)C16—C15—C24—C23−1.6 (2)
C9—C8—C13—C14−174.00 (12)C14—C15—C24—C23175.93 (13)
C7—C8—C13—C1411.71 (19)C22—C23—C24—O3177.46 (15)
C12—C13—C14—O2−158.80 (14)C22—C23—C24—C150.3 (2)
C8—C13—C14—O216.44 (19)C15—C24—O3—C25−170.97 (15)
C12—C13—C14—C1520.27 (18)C23—C24—O3—C2511.8 (2)
C8—C13—C14—C15−164.48 (12)
Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.583.288 (2)134
C19—H19···Cg1ii0.932.773.585 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C10—H10⋯O1i0.932.583.288 (2)134
C19—H19⋯Cg1ii0.932.773.585 (3)147

Symmetry codes: (i) ; (ii) .

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Authors:  I Bennett; N J Broom; R Cassels; J S Elder; N D Masson; P J O'Hanlon
Journal:  Bioorg Med Chem Lett       Date:  1999-07-05       Impact factor: 2.823

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  (2-Benzoyl-phen-yl)(3,4-dimethyl-phen-yl)methanone.

Authors:  G Jagadeesan; K Sethusankar; R Sivasakthikumaran; Arasambattu K Mohanakrishnan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-30

4.  [2,7-Dimeth-oxy-8-(2-naphtho-yl)naphthalen-1-yl](naphthalen-2-yl)methanone.

Authors:  Takehiro Tsumuki; Daichi Hijikata; Akiko Okamoto; Hideaki Oike; Noriyuki Yonezawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-23

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  [2-(2-Meth-oxy-1-naphtho-yl)phen-yl](1-naphth-yl)methanone.

Authors:  G Jagadeesan; K Sethusankar; R Sivasakthikumaran; Arasambattu K Mohanakrishnan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-29
  1 in total

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