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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1760.
Published online 2010 June 23. doi:  10.1107/S1600536810022610
PMCID: PMC3006997

1,3-Bis(4-chloro­phen­yl)-1-methyl-1H-benzo[f]chromene

Abstract

The title compound, C26H18Cl2O, is a heterocyclic structure consisting of a benzo[f]chromene ring and two aromatic rings. The non-H atoms of the benzo[f]chromene ring are almost coplanar (rms deviation = 0.107 Å), and the methyl C atom lies 1.340 (4) Å from the mean plane of the benzo[f]chromene ring. The chromene ring forms dihedral angles of 88.45 (2)° with the benzene ring linked to the quaternary C atom and 50.74 (3)° with the benzene ring linked to the 3-position, while the dihedral angle between the two benzene rings is 67.58 (3)°.

Related literature

For the construction of a 4H-chromene scaffold, see: Shi & Shi (2007 [triangle]); Zeni & Larrock (2004 [triangle]). For the biological and pharmacological activity of 4H-chromene derivatives, see: Kidwai et al. (2005 [triangle]). For 4H-chromene derivatives possessing a tertiary carbon in the scaffold, see: Liu et al. (2010 [triangle]); Wang & Zhu (2010 [triangle]). For iron trichloride-catalysed synthesis of 4H-chromenes, see: Kozlikovskii et al. (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1760-scheme1.jpg

Experimental

Crystal data

  • C26H18Cl2O
  • M r = 417.33
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1760-efi1.jpg
  • a = 8.9554 (6) Å
  • b = 9.4439 (6) Å
  • c = 12.3206 (7) Å
  • α = 93.511 (2)°
  • β = 102.0453 (15)°
  • γ = 94.287 (2)°
  • V = 1013.05 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 296 K
  • 0.42 × 0.37 × 0.28 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.874, T max = 0.910
  • 10050 measured reflections
  • 4596 independent reflections
  • 2783 reflections with F 2 > 2σ(F 2)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.095
  • S = 1.00
  • 4596 reflections
  • 264 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022610/zq2041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022610/zq2041Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Professor Jian-Ming Gu of Zhejiang University for the crystal structure analysis.

supplementary crystallographic information

Comment

Chromenes (2H- and 4H-chromenes) constitute an important class of scaffolds found in many naturally occurring and synthetic molecules showing unique biological and pharmacological activities including spasmolytic, diuretic, anticoagulant, anticancer activities and so on. In this article, the crystal structure of the title compoud 1,3-di(4-chloro-phenyl)-1-methyl-1H-benzo[f]chromene was determined (Fig. 1–2). Its main structure unit consists of a benzo[f]chromene ring and two aromatic rings, in which the non-H atoms of the benzo[f]chromene ring are almost coplanar, and the methyl atom C26 lies 1.340 (4) Å from the benzo[f]chromene ring. The chromene ring forms dihedral angles of 88.45 (2)° with the benzene ring linked to the quaternary carbon atom C1, and 50.74 (3)° with the other benzene ring linked to C12, while the dihedral angle between the two benzene rings is 67.58 (3)°.

Experimental

The title compound was synthesized by treating (E)-1,3-bis(4-chlorophenyl)but-2-en-1-one (0.291 g,1 mmol) with 2-naphthol (0.144 g,1 mmol) in the presence of ferric trichloride (0.16 g, 1.0 mmol) as a catalyst in 1,2-dichloroethane (3 ml) under stirring at reflux for 6 h. Upon completion, the resulting mixture was diluted with dichloromethane (10 ml) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (200–300 mesh) using Petroleum ether-EtOAc (30:1) as eluent to give the title compound (0.19 g, 40%). Suitable crystals of the title compound were obtained by slow evaporation of ethanol solution at room temperature.

Refinement

H atoms were placed in calculated position with C—H = 0.96 Å (sp), C—H = 0.93 Å (sp2), C—H = 0.93 Å (aromatic H atoms). All H atoms are included in the final cycles of refinement using a riding mode, with Uiso(H) = 1.2Ueq of the carrier atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with the atomic labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The packing of the crystal structure of the title compound. The C, O and Cl atoms are grey, red and brown, respectively.

Crystal data

C26H18Cl2OZ = 2
Mr = 417.33F(000) = 432.00
Triclinic, P1Dx = 1.368 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 8.9554 (6) ÅCell parameters from 6736 reflections
b = 9.4439 (6) Åθ = 3.0–27.4°
c = 12.3206 (7) ŵ = 0.34 mm1
α = 93.511 (2)°T = 296 K
β = 102.0453 (15)°Chunk, colorless
γ = 94.287 (2)°0.42 × 0.37 × 0.28 mm
V = 1013.05 (11) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer2783 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.021
ω scansθmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −11→11
Tmin = 0.874, Tmax = 0.910k = −12→12
10050 measured reflectionsl = −15→14
4596 independent reflections

Refinement

Refinement on F2w = 1/[σ2(Fo2) + (0.001P)2 + 0.920P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042(Δ/σ)max < 0.001
wR(F2) = 0.095Δρmax = 0.28 e Å3
S = 1.00Δρmin = −0.33 e Å3
4596 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008)
264 parametersExtinction coefficient: 0.0188 (6)
H-atom parameters constrained

Special details

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

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

xyzUiso*/Ueq
Cl10.25919 (11)−0.05748 (9)0.82025 (6)0.0899 (3)
Cl20.54898 (11)0.29006 (9)−0.01095 (6)0.0875 (2)
O10.27277 (19)0.50754 (14)0.53308 (12)0.0492 (4)
C10.1329 (2)0.4692 (2)0.29332 (18)0.0405 (5)
C20.2049 (2)0.6121 (2)0.35548 (17)0.0380 (4)
C30.2145 (2)0.7416 (2)0.29947 (18)0.0406 (5)
C40.1688 (2)0.7468 (2)0.1828 (2)0.0521 (6)
C50.1790 (3)0.8718 (2)0.1324 (2)0.0614 (7)
C60.2364 (3)0.9992 (2)0.1961 (2)0.0635 (7)
C70.2840 (2)0.9991 (2)0.3080 (2)0.0543 (6)
C80.2758 (2)0.8720 (2)0.3627 (2)0.0430 (5)
C90.3277 (2)0.8730 (2)0.4787 (2)0.0473 (5)
C100.3245 (2)0.7510 (2)0.53063 (19)0.0465 (5)
C110.2644 (2)0.6220 (2)0.46756 (18)0.0403 (4)
C120.2041 (2)0.3771 (2)0.48333 (18)0.0406 (5)
C130.1397 (2)0.3577 (2)0.37734 (19)0.0431 (5)
C140.2173 (2)0.2685 (2)0.56609 (18)0.0401 (4)
C150.0923 (2)0.1769 (2)0.5723 (2)0.0542 (6)
C160.1045 (2)0.0765 (2)0.6511 (2)0.0609 (7)
C170.2428 (3)0.0687 (2)0.7219 (2)0.0532 (6)
C180.3693 (2)0.1574 (2)0.7168 (2)0.0538 (6)
C190.3551 (2)0.2575 (2)0.63937 (19)0.0483 (5)
C200.2310 (2)0.4205 (2)0.21085 (17)0.0419 (5)
C210.1736 (3)0.3746 (2)0.09965 (19)0.0542 (6)
C220.2691 (3)0.3322 (2)0.0309 (2)0.0618 (7)
C230.4242 (3)0.3367 (2)0.0735 (2)0.0571 (6)
C240.4842 (2)0.3788 (2)0.1839 (2)0.0547 (6)
C250.3879 (2)0.4192 (2)0.25085 (19)0.0475 (5)
C26−0.0378 (2)0.4756 (2)0.2390 (2)0.0551 (6)
H40.13090.66300.13890.063*
H50.14740.87170.05560.074*
H60.24201.08390.16190.076*
H70.32291.08420.34980.065*
H90.36480.95860.52020.057*
H100.36150.75230.60710.056*
H130.09390.26700.35100.052*
H15−0.00100.18230.52340.065*
H160.01980.01560.65550.073*
H180.46290.15010.76490.065*
H190.44000.31900.63630.058*
H210.06880.37240.07070.065*
H220.22870.3010−0.04320.074*
H240.58890.37980.21270.066*
H250.42890.44680.32560.057*
H261−0.04690.54280.18310.066*
H262−0.08060.38310.20520.066*
H263−0.09210.50470.29480.066*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1224 (7)0.0753 (5)0.0833 (5)0.0203 (4)0.0317 (5)0.0476 (4)
Cl20.1234 (7)0.0946 (6)0.0600 (4)0.0380 (5)0.0429 (4)0.0140 (4)
O10.0640 (10)0.0346 (8)0.0440 (8)−0.0043 (7)0.0019 (7)0.0087 (6)
C10.0442 (12)0.0305 (10)0.0439 (11)0.0003 (9)0.0033 (9)0.0046 (8)
C20.0383 (11)0.0323 (11)0.0446 (11)0.0043 (9)0.0101 (9)0.0065 (9)
C30.0414 (11)0.0340 (11)0.0490 (12)0.0066 (9)0.0127 (10)0.0096 (9)
C40.0627 (15)0.0421 (13)0.0529 (14)0.0086 (11)0.0117 (12)0.0126 (10)
C50.0797 (19)0.0519 (15)0.0579 (15)0.0144 (13)0.0186 (14)0.0216 (12)
C60.0733 (18)0.0409 (14)0.085 (2)0.0116 (13)0.0274 (15)0.0283 (13)
C70.0544 (14)0.0338 (12)0.0771 (18)0.0028 (10)0.0179 (13)0.0117 (11)
C80.0401 (11)0.0315 (11)0.0598 (14)0.0037 (9)0.0150 (10)0.0062 (9)
C90.0452 (13)0.0346 (11)0.0615 (14)−0.0016 (9)0.0131 (11)−0.0011 (10)
C100.0487 (13)0.0407 (12)0.0469 (12)−0.0022 (10)0.0058 (10)−0.0006 (10)
C110.0410 (11)0.0336 (11)0.0466 (12)0.0017 (9)0.0095 (10)0.0083 (9)
C120.0391 (11)0.0332 (11)0.0493 (12)0.0003 (9)0.0083 (10)0.0086 (9)
C130.0465 (12)0.0311 (11)0.0502 (13)−0.0014 (9)0.0075 (10)0.0070 (9)
C140.0425 (12)0.0356 (11)0.0448 (11)0.0046 (9)0.0135 (10)0.0080 (9)
C150.0407 (13)0.0519 (14)0.0718 (16)0.0053 (11)0.0108 (12)0.0225 (12)
C160.0542 (15)0.0499 (15)0.0861 (19)0.0028 (11)0.0262 (14)0.0271 (13)
C170.0697 (17)0.0452 (13)0.0521 (14)0.0150 (12)0.0220 (13)0.0196 (11)
C180.0573 (15)0.0542 (15)0.0485 (13)0.0079 (12)0.0046 (11)0.0126 (11)
C190.0467 (13)0.0471 (13)0.0496 (13)−0.0023 (10)0.0076 (11)0.0084 (10)
C200.0541 (13)0.0300 (10)0.0390 (11)0.0037 (9)0.0031 (10)0.0066 (8)
C210.0660 (16)0.0473 (14)0.0425 (12)0.0097 (12)−0.0054 (11)0.0039 (10)
C220.093 (2)0.0555 (16)0.0343 (12)0.0178 (14)0.0038 (13)0.0045 (10)
C230.087 (2)0.0459 (14)0.0441 (13)0.0187 (13)0.0209 (13)0.0105 (10)
C240.0596 (15)0.0562 (15)0.0498 (14)0.0118 (12)0.0125 (12)0.0057 (11)
C250.0542 (14)0.0457 (13)0.0403 (11)0.0046 (11)0.0058 (10)0.0004 (9)
C260.0474 (14)0.0512 (14)0.0624 (15)0.0012 (11)0.0015 (11)0.0098 (11)

Geometric parameters (Å, °)

Cl1—C171.743 (2)C18—C191.378 (3)
Cl2—C231.740 (3)C20—C211.389 (2)
O1—C111.385 (2)C20—C251.389 (3)
O1—C121.381 (2)C21—C221.386 (4)
C1—C21.536 (2)C22—C231.375 (4)
C1—C131.517 (3)C23—C241.375 (3)
C1—C201.547 (3)C24—C251.371 (3)
C1—C261.542 (3)C4—H40.930
C2—C31.446 (3)C5—H50.930
C2—C111.367 (2)C6—H60.930
C3—C41.415 (3)C7—H70.930
C3—C81.424 (2)C9—H90.930
C4—C51.373 (3)C10—H100.930
C5—C61.397 (3)C13—H130.930
C6—C71.356 (4)C15—H150.930
C7—C81.416 (3)C16—H160.930
C8—C91.407 (3)C18—H180.930
C9—C101.353 (3)C19—H190.930
C10—C111.411 (2)C21—H210.930
C12—C131.308 (2)C22—H220.930
C12—C141.484 (3)C24—H240.930
C14—C151.381 (3)C25—H250.930
C14—C191.383 (2)C26—H2610.960
C15—C161.391 (3)C26—H2620.960
C16—C171.368 (3)C26—H2630.960
C17—C181.372 (3)
C11—O1—C12117.40 (15)C21—C22—C23119.3 (2)
C2—C1—C13108.24 (16)Cl2—C23—C22120.80 (18)
C2—C1—C20109.59 (17)Cl2—C23—C24118.6 (2)
C2—C1—C26111.80 (18)C22—C23—C24120.6 (2)
C13—C1—C20106.20 (17)C23—C24—C25119.3 (2)
C13—C1—C26106.86 (18)C20—C25—C24122.2 (2)
C20—C1—C26113.82 (17)C3—C4—H4119.0
C1—C2—C3122.33 (17)C5—C4—H4119.0
C1—C2—C11120.91 (18)C4—C5—H5119.8
C3—C2—C11116.76 (17)C6—C5—H5119.8
C2—C3—C4123.51 (18)C5—C6—H6120.1
C2—C3—C8119.56 (19)C7—C6—H6120.1
C4—C3—C8116.9 (2)C6—C7—H7119.3
C3—C4—C5121.9 (2)C8—C7—H7119.3
C4—C5—C6120.3 (2)C8—C9—H9119.5
C5—C6—C7119.8 (2)C10—C9—H9119.5
C6—C7—C8121.4 (2)C9—C10—H10120.4
C3—C8—C7119.6 (2)C11—C10—H10120.4
C3—C8—C9119.6 (2)C1—C13—H13116.9
C7—C8—C9120.82 (19)C12—C13—H13116.9
C8—C9—C10120.91 (19)C14—C15—H15119.6
C9—C10—C11119.3 (2)C16—C15—H15119.6
O1—C11—C2124.47 (17)C15—C16—H16120.5
O1—C11—C10111.76 (17)C17—C16—H16120.5
C2—C11—C10123.8 (2)C17—C18—H18120.6
O1—C12—C13122.56 (19)C19—C18—H18120.6
O1—C12—C14110.38 (16)C14—C19—H19119.3
C13—C12—C14127.05 (18)C18—C19—H19119.3
C1—C13—C12126.12 (19)C20—C21—H21119.3
C12—C14—C15120.82 (19)C22—C21—H21119.3
C12—C14—C19120.67 (19)C21—C22—H22120.4
C15—C14—C19118.5 (2)C23—C22—H22120.4
C14—C15—C16120.7 (2)C23—C24—H24120.4
C15—C16—C17119.1 (2)C25—C24—H24120.4
Cl1—C17—C16119.3 (2)C20—C25—H25118.9
Cl1—C17—C18119.22 (18)C24—C25—H25118.9
C16—C17—C18121.5 (2)C1—C26—H261109.5
C17—C18—C19118.9 (2)C1—C26—H262109.5
C14—C19—C18121.4 (2)C1—C26—H263109.5
C1—C20—C21124.8 (2)H261—C26—H262109.5
C1—C20—C25118.00 (17)H261—C26—H263109.5
C21—C20—C25117.2 (2)H262—C26—H263109.5
C20—C21—C22121.4 (2)
C11—O1—C12—C133.5 (3)C5—C6—C7—C8−0.5 (4)
C11—O1—C12—C14−177.32 (19)C6—C7—C8—C3−0.9 (3)
C12—O1—C11—C2−6.0 (3)C6—C7—C8—C9179.0 (2)
C12—O1—C11—C10173.84 (19)C3—C8—C9—C102.0 (3)
C2—C1—C13—C12−3.8 (3)C7—C8—C9—C10−177.9 (2)
C13—C1—C2—C3−179.1 (2)C8—C9—C10—C11−1.7 (3)
C13—C1—C2—C111.3 (2)C9—C10—C11—O1178.7 (2)
C2—C1—C20—C21−131.0 (2)C9—C10—C11—C2−1.5 (3)
C2—C1—C20—C2550.4 (2)O1—C12—C13—C11.6 (3)
C20—C1—C2—C365.5 (2)O1—C12—C14—C15133.8 (2)
C20—C1—C2—C11−114.1 (2)O1—C12—C14—C19−45.6 (2)
C26—C1—C2—C3−61.6 (2)C13—C12—C14—C15−47.0 (3)
C26—C1—C2—C11118.8 (2)C13—C12—C14—C19133.5 (2)
C13—C1—C20—C21112.3 (2)C14—C12—C13—C1−177.5 (2)
C13—C1—C20—C25−66.3 (2)C12—C14—C15—C16−179.0 (2)
C20—C1—C13—C12113.8 (2)C12—C14—C19—C18179.9 (2)
C26—C1—C13—C12−124.4 (2)C15—C14—C19—C180.4 (3)
C26—C1—C20—C21−5.0 (3)C19—C14—C15—C160.4 (3)
C26—C1—C20—C25176.4 (2)C14—C15—C16—C17−0.6 (4)
C1—C2—C3—C4−4.6 (3)C15—C16—C17—Cl1−179.6 (2)
C1—C2—C3—C8176.9 (2)C15—C16—C17—C18−0.0 (3)
C1—C2—C11—O13.4 (3)Cl1—C17—C18—C19−179.58 (19)
C1—C2—C11—C10−176.4 (2)C16—C17—C18—C190.8 (3)
C3—C2—C11—O1−176.2 (2)C17—C18—C19—C14−1.0 (3)
C3—C2—C11—C104.0 (3)C1—C20—C21—C22−179.8 (2)
C11—C2—C3—C4175.1 (2)C1—C20—C25—C24−179.5 (2)
C11—C2—C3—C8−3.4 (3)C21—C20—C25—C241.8 (3)
C2—C3—C4—C5179.8 (2)C25—C20—C21—C22−1.2 (3)
C2—C3—C8—C7−179.5 (2)C20—C21—C22—C23−0.6 (3)
C2—C3—C8—C90.6 (3)C21—C22—C23—Cl2−177.82 (19)
C4—C3—C8—C71.9 (3)C21—C22—C23—C241.9 (3)
C4—C3—C8—C9−178.0 (2)Cl2—C23—C24—C25178.40 (19)
C8—C3—C4—C5−1.7 (3)C22—C23—C24—C25−1.3 (3)
C3—C4—C5—C60.4 (4)C23—C24—C25—C20−0.6 (3)
C4—C5—C6—C70.7 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2041).

References

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