Literature DB >> 22590420

(2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(2,6-difluoro-phen-yl)prop-2-en-1-one.

Hoong-Kun Fun, Tze Shyang Chia, S Samshuddin, B Narayana, B K Sarojini.   

Abstract

In the title compound, C(28)H(18)F(4)O(2), the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluoro-benzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluoro-benzene rings is 87.81 (6)°. The meth-oxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C-O-C(ar)-C(ar) [-0.06 (15)°] and C-C-C(ar)-C(ar) [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, mol-ecules are linked by C-H⋯F and C-H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID: 22590420      PMCID: PMC3344658          DOI: 10.1107/S160053681201820X

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


Related literature

For related structures and background to terphenyl chalcones, see: Fun et al. (2011 ▶, 2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C28H18F4O2 M = 462.42 Triclinic, a = 8.9624 (5) Å b = 10.2127 (6) Å c = 13.3281 (7) Å α = 67.780 (1)° β = 86.776 (1)° γ = 85.293 (1)° V = 1125.10 (11) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 100 K 0.25 × 0.20 × 0.11 mm

Data collection

Bruker APEX Duo CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.974, T max = 0.989 28220 measured reflections 8063 independent reflections 6097 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.144 S = 1.02 8063 reflections 308 parameters H-atom parameters constrained Δρmax = 0.40 e Å−3 Δρmin = −0.35 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201820X/hb6753sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201820X/hb6753Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681201820X/hb6753Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C28H18F4O2Z = 2
Mr = 462.42F(000) = 476
Triclinic, P1Dx = 1.365 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9624 (5) ÅCell parameters from 7563 reflections
b = 10.2127 (6) Åθ = 2.3–32.4°
c = 13.3281 (7) ŵ = 0.11 mm1
α = 67.780 (1)°T = 100 K
β = 86.776 (1)°Block, colourless
γ = 85.293 (1)°0.25 × 0.20 × 0.11 mm
V = 1125.10 (11) Å3
Bruker APEX Duo CCD diffractometer8063 independent reflections
Radiation source: fine-focus sealed tube6097 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 32.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.974, Tmax = 0.989k = −15→14
28220 measured reflectionsl = −20→18
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) = 0.144H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0774P)2 + 0.2553P] where P = (Fo2 + 2Fc2)/3
8063 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.35 e Å3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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
F10.17366 (10)0.87097 (10)−0.57879 (6)0.03431 (19)
F20.40523 (9)0.37977 (9)0.20352 (6)0.03302 (19)
F30.15771 (9)0.45771 (9)0.49909 (6)0.03172 (19)
F40.54429 (8)0.99409 (9)0.24888 (6)0.02763 (17)
O1−0.18938 (9)0.62125 (9)0.08627 (7)0.02127 (17)
O2−0.12638 (9)0.79463 (9)0.21502 (7)0.02271 (17)
C10.09479 (14)0.69493 (13)−0.29224 (10)0.0227 (2)
H1A0.07110.6060−0.24300.027*
C20.11646 (14)0.71665 (14)−0.40139 (10)0.0261 (2)
H2A0.10740.6437−0.42590.031*
C30.15174 (13)0.84918 (14)−0.47200 (9)0.0240 (2)
C40.16684 (13)0.96077 (13)−0.43948 (9)0.0221 (2)
H4A0.19121.0490−0.48950.027*
C50.14462 (12)0.93777 (12)−0.32982 (9)0.0187 (2)
H5A0.15421.0113−0.30610.022*
C60.10798 (12)0.80452 (11)−0.25527 (8)0.01738 (19)
C70.08139 (12)0.78028 (11)−0.13880 (9)0.01654 (19)
C80.17578 (12)0.83272 (11)−0.08525 (8)0.01669 (19)
H8A0.25810.8809−0.12240.020*
C90.14842 (11)0.81386 (11)0.02356 (8)0.01554 (18)
C100.02237 (11)0.74476 (11)0.07864 (8)0.01598 (19)
C11−0.07150 (11)0.68975 (11)0.02521 (9)0.01676 (19)
C12−0.04140 (12)0.70569 (11)−0.08225 (9)0.01702 (19)
H12A−0.10250.6670−0.11650.020*
C13−0.01691 (11)0.72807 (11)0.19450 (9)0.01693 (19)
C140.07608 (12)0.62893 (12)0.28288 (9)0.0188 (2)
H14A0.06010.62900.35240.023*
C150.18306 (12)0.53861 (11)0.26616 (9)0.0178 (2)
H15A0.20000.54740.19450.021*
C160.27629 (12)0.42826 (12)0.34593 (9)0.0182 (2)
C170.26488 (13)0.38889 (13)0.45849 (9)0.0218 (2)
C180.35385 (14)0.28272 (14)0.53126 (10)0.0256 (2)
H18A0.34120.26080.60540.031*
C190.46305 (14)0.20924 (14)0.49095 (10)0.0279 (3)
H19A0.52470.13770.53860.033*
C200.48077 (14)0.24180 (14)0.38016 (10)0.0275 (3)
H20A0.55330.19270.35280.033*
C210.38792 (13)0.34881 (13)0.31183 (9)0.0221 (2)
C220.25400 (11)0.86676 (11)0.07971 (8)0.01586 (19)
C230.40626 (12)0.82182 (12)0.08352 (9)0.0199 (2)
H23A0.44140.76290.04740.024*
C240.50582 (12)0.86360 (13)0.14022 (9)0.0224 (2)
H24A0.60660.83280.14350.027*
C250.44924 (12)0.95271 (12)0.19155 (9)0.0201 (2)
C260.30110 (13)1.00312 (12)0.18763 (9)0.0202 (2)
H26A0.26781.06500.22170.024*
C270.20311 (12)0.95877 (11)0.13136 (9)0.0182 (2)
H27A0.10260.99080.12810.022*
C28−0.28775 (13)0.56257 (13)0.03620 (10)0.0231 (2)
H28A−0.36410.51570.08770.035*
H28B−0.23190.49550.01170.035*
H28C−0.33340.6371−0.02450.035*
U11U22U33U12U13U23
F10.0361 (4)0.0511 (5)0.0166 (3)−0.0008 (4)0.0005 (3)−0.0142 (3)
F20.0317 (4)0.0454 (5)0.0188 (3)0.0145 (3)−0.0004 (3)−0.0119 (3)
F30.0370 (4)0.0357 (4)0.0187 (3)0.0152 (3)0.0003 (3)−0.0097 (3)
F40.0223 (3)0.0393 (4)0.0230 (3)−0.0097 (3)−0.0061 (3)−0.0114 (3)
O10.0178 (4)0.0265 (4)0.0193 (4)−0.0074 (3)0.0010 (3)−0.0073 (3)
O20.0168 (4)0.0280 (4)0.0234 (4)0.0035 (3)−0.0005 (3)−0.0108 (3)
C10.0253 (5)0.0232 (5)0.0213 (5)−0.0032 (4)−0.0009 (4)−0.0099 (4)
C20.0286 (6)0.0317 (6)0.0230 (5)−0.0022 (5)−0.0014 (4)−0.0160 (5)
C30.0204 (5)0.0365 (6)0.0152 (5)0.0014 (4)−0.0014 (4)−0.0105 (4)
C40.0188 (5)0.0264 (5)0.0177 (5)0.0002 (4)−0.0017 (4)−0.0046 (4)
C50.0164 (4)0.0209 (5)0.0180 (5)−0.0001 (4)−0.0020 (4)−0.0064 (4)
C60.0151 (4)0.0207 (5)0.0164 (4)−0.0002 (3)−0.0016 (3)−0.0070 (4)
C70.0160 (4)0.0169 (4)0.0166 (4)0.0005 (3)−0.0018 (3)−0.0063 (4)
C80.0144 (4)0.0188 (4)0.0165 (4)−0.0007 (3)−0.0003 (3)−0.0063 (4)
C90.0125 (4)0.0172 (4)0.0167 (4)0.0013 (3)−0.0018 (3)−0.0063 (4)
C100.0141 (4)0.0173 (4)0.0156 (4)0.0011 (3)−0.0019 (3)−0.0054 (4)
C110.0145 (4)0.0170 (4)0.0173 (4)−0.0007 (3)−0.0008 (3)−0.0048 (4)
C120.0160 (4)0.0179 (4)0.0174 (4)−0.0012 (3)−0.0023 (3)−0.0067 (4)
C130.0145 (4)0.0187 (4)0.0178 (5)−0.0014 (3)−0.0007 (3)−0.0070 (4)
C140.0175 (5)0.0228 (5)0.0156 (4)0.0006 (4)−0.0010 (4)−0.0070 (4)
C150.0167 (4)0.0201 (5)0.0157 (4)−0.0007 (4)−0.0011 (3)−0.0056 (4)
C160.0161 (4)0.0210 (5)0.0169 (5)0.0000 (4)−0.0010 (4)−0.0067 (4)
C170.0215 (5)0.0239 (5)0.0191 (5)0.0035 (4)−0.0005 (4)−0.0081 (4)
C180.0260 (6)0.0292 (6)0.0180 (5)0.0046 (4)−0.0031 (4)−0.0058 (4)
C190.0242 (6)0.0306 (6)0.0235 (6)0.0067 (5)−0.0042 (4)−0.0053 (5)
C200.0220 (5)0.0328 (6)0.0239 (6)0.0095 (5)−0.0010 (4)−0.0086 (5)
C210.0190 (5)0.0283 (5)0.0173 (5)0.0034 (4)−0.0003 (4)−0.0079 (4)
C220.0130 (4)0.0187 (4)0.0149 (4)−0.0010 (3)−0.0015 (3)−0.0050 (4)
C230.0145 (4)0.0244 (5)0.0213 (5)0.0008 (4)−0.0011 (4)−0.0094 (4)
C240.0130 (4)0.0305 (6)0.0222 (5)−0.0002 (4)−0.0033 (4)−0.0082 (4)
C250.0180 (5)0.0254 (5)0.0158 (4)−0.0059 (4)−0.0043 (4)−0.0050 (4)
C260.0206 (5)0.0220 (5)0.0192 (5)−0.0026 (4)−0.0009 (4)−0.0087 (4)
C270.0147 (4)0.0203 (5)0.0194 (5)0.0008 (3)−0.0024 (3)−0.0072 (4)
C280.0171 (5)0.0268 (5)0.0276 (6)−0.0058 (4)−0.0004 (4)−0.0117 (5)
F1—C31.3602 (13)C13—C141.4756 (15)
F2—C211.3585 (13)C14—C151.3440 (15)
F3—C171.3519 (13)C14—H14A0.9300
F4—C251.3656 (13)C15—C161.4621 (15)
O1—C111.3645 (13)C15—H15A0.9300
O1—C281.4274 (14)C16—C171.3985 (15)
O2—C131.2249 (13)C16—C211.4002 (15)
C1—C21.3908 (16)C17—C181.3791 (16)
C1—C61.3981 (16)C18—C191.3910 (17)
C1—H1A0.9300C18—H18A0.9300
C2—C31.3751 (18)C19—C201.3882 (17)
C2—H2A0.9300C19—H19A0.9300
C3—C41.3823 (18)C20—C211.3782 (16)
C4—C51.3951 (15)C20—H20A0.9300
C4—H4A0.9300C22—C271.3958 (15)
C5—C61.4003 (15)C22—C231.4010 (14)
C5—H5A0.9300C23—C241.3897 (16)
C6—C71.4850 (15)C23—H23A0.9300
C7—C81.3939 (15)C24—C251.3819 (17)
C7—C121.4034 (15)C24—H24A0.9300
C8—C91.3990 (14)C25—C261.3805 (16)
C8—H8A0.9300C26—C271.3912 (15)
C9—C101.3996 (14)C26—H26A0.9300
C9—C221.4888 (15)C27—H27A0.9300
C10—C111.4064 (15)C28—H28A0.9600
C10—C131.5123 (14)C28—H28B0.9600
C11—C121.3921 (15)C28—H28C0.9600
C12—H12A0.9300
C11—O1—C28117.58 (9)C14—C15—H15A115.8
C2—C1—C6121.10 (11)C16—C15—H15A115.8
C2—C1—H1A119.5C17—C16—C21113.73 (10)
C6—C1—H1A119.5C17—C16—C15126.22 (10)
C3—C2—C1118.01 (11)C21—C16—C15120.04 (10)
C3—C2—H2A121.0F3—C17—C18117.61 (10)
C1—C2—H2A121.0F3—C17—C16117.92 (10)
F1—C3—C2118.31 (11)C18—C17—C16124.46 (10)
F1—C3—C4118.56 (11)C17—C18—C19118.36 (11)
C2—C3—C4123.13 (11)C17—C18—H18A120.8
C3—C4—C5118.34 (11)C19—C18—H18A120.8
C3—C4—H4A120.8C20—C19—C18120.55 (11)
C5—C4—H4A120.8C20—C19—H19A119.7
C4—C5—C6120.35 (11)C18—C19—H19A119.7
C4—C5—H5A119.8C21—C20—C19118.19 (11)
C6—C5—H5A119.8C21—C20—H20A120.9
C1—C6—C5119.07 (10)C19—C20—H20A120.9
C1—C6—C7120.38 (10)F2—C21—C20117.95 (10)
C5—C6—C7120.55 (10)F2—C21—C16117.34 (10)
C8—C7—C12119.51 (10)C20—C21—C16124.70 (11)
C8—C7—C6120.74 (9)C27—C22—C23118.94 (10)
C12—C7—C6119.75 (10)C27—C22—C9120.92 (9)
C7—C8—C9120.89 (10)C23—C22—C9120.12 (9)
C7—C8—H8A119.6C24—C23—C22121.32 (10)
C9—C8—H8A119.6C24—C23—H23A119.3
C8—C9—C10119.59 (10)C22—C23—H23A119.3
C8—C9—C22119.71 (9)C25—C24—C23117.43 (10)
C10—C9—C22120.71 (9)C25—C24—H24A121.3
C9—C10—C11119.51 (9)C23—C24—H24A121.3
C9—C10—C13121.81 (9)F4—C25—C26117.91 (10)
C11—C10—C13118.68 (9)F4—C25—C24118.65 (10)
O1—C11—C12124.20 (10)C26—C25—C24123.44 (11)
O1—C11—C10115.25 (9)C25—C26—C27118.14 (10)
C12—C11—C10120.55 (10)C25—C26—H26A120.9
C11—C12—C7119.86 (10)C27—C26—H26A120.9
C11—C12—H12A120.1C26—C27—C22120.70 (10)
C7—C12—H12A120.1C26—C27—H27A119.7
O2—C13—C14120.22 (10)C22—C27—H27A119.7
O2—C13—C10120.30 (9)O1—C28—H28A109.5
C14—C13—C10119.47 (9)O1—C28—H28B109.5
C15—C14—C13122.15 (10)H28A—C28—H28B109.5
C15—C14—H14A118.9O1—C28—H28C109.5
C13—C14—H14A118.9H28A—C28—H28C109.5
C14—C15—C16128.48 (10)H28B—C28—H28C109.5
C6—C1—C2—C30.19 (18)C11—C10—C13—C14109.02 (11)
C1—C2—C3—F1179.74 (11)O2—C13—C14—C15169.89 (11)
C1—C2—C3—C40.16 (19)C10—C13—C14—C15−8.99 (16)
F1—C3—C4—C5−179.84 (10)C13—C14—C15—C16−175.29 (11)
C2—C3—C4—C5−0.25 (18)C14—C15—C16—C174.5 (2)
C3—C4—C5—C60.00 (16)C14—C15—C16—C21−176.78 (12)
C2—C1—C6—C5−0.43 (17)C21—C16—C17—F3−178.53 (11)
C2—C1—C6—C7178.74 (10)C15—C16—C17—F30.30 (18)
C4—C5—C6—C10.33 (16)C21—C16—C17—C180.26 (18)
C4—C5—C6—C7−178.83 (10)C15—C16—C17—C18179.09 (12)
C1—C6—C7—C8137.19 (11)F3—C17—C18—C19178.96 (12)
C5—C6—C7—C8−43.66 (14)C16—C17—C18—C190.2 (2)
C1—C6—C7—C12−43.81 (15)C17—C18—C19—C20−0.4 (2)
C5—C6—C7—C12135.34 (11)C18—C19—C20—C210.3 (2)
C12—C7—C8—C9−0.99 (15)C19—C20—C21—F2−179.68 (12)
C6—C7—C8—C9178.01 (9)C19—C20—C21—C160.2 (2)
C7—C8—C9—C10−1.73 (15)C17—C16—C21—F2179.42 (11)
C7—C8—C9—C22177.95 (9)C15—C16—C21—F20.51 (17)
C8—C9—C10—C112.77 (15)C17—C16—C21—C20−0.45 (18)
C22—C9—C10—C11−176.91 (9)C15—C16—C21—C20−179.36 (12)
C8—C9—C10—C13−176.84 (9)C8—C9—C22—C27125.20 (11)
C22—C9—C10—C133.48 (15)C10—C9—C22—C27−55.12 (14)
C28—O1—C11—C12−0.06 (15)C8—C9—C22—C23−56.29 (14)
C28—O1—C11—C10−179.63 (9)C10—C9—C22—C23123.38 (11)
C9—C10—C11—O1178.46 (9)C27—C22—C23—C241.97 (16)
C13—C10—C11—O1−1.92 (14)C9—C22—C23—C24−176.57 (10)
C9—C10—C11—C12−1.12 (15)C22—C23—C24—C25−0.82 (17)
C13—C10—C11—C12178.50 (9)C23—C24—C25—F4179.25 (10)
O1—C11—C12—C7178.86 (10)C23—C24—C25—C26−1.08 (18)
C10—C11—C12—C7−1.60 (15)F4—C25—C26—C27−178.59 (10)
C8—C7—C12—C112.64 (15)C24—C25—C26—C271.74 (17)
C6—C7—C12—C11−176.37 (9)C25—C26—C27—C22−0.51 (16)
C9—C10—C13—O2109.75 (12)C23—C22—C27—C26−1.27 (16)
C11—C10—C13—O2−69.86 (14)C9—C22—C27—C26177.25 (10)
C9—C10—C13—C14−71.37 (14)
D—H···AD—HH···AD···AD—H···A
C2—H2A···F3i0.932.463.3655 (18)164
C8—H8A···F4ii0.932.453.3726 (13)170
C24—H24A···O2iii0.932.573.4371 (14)155
C20—H20A···Cg1iv0.932.833.5082 (14)130
C27—H27A···Cg2v0.932.683.4068 (12)136
C28—H28B···Cg2vi0.962.903.7990 (15)157
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
C2—H2A⋯F3i0.932.463.3655 (18)164
C8—H8A⋯F4ii0.932.453.3726 (13)170
C24—H24A⋯O2iii0.932.573.4371 (14)155
C20—H20ACg1iv0.932.833.5082 (14)130
C27—H27ACg2v0.932.683.4068 (12)136
C28—H28BCg2vi0.962.903.7990 (15)157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  4 in total

1.  A short history of SHELX.

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

2.  (E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(6-meth-oxy-naphthalen-2-yl)prop-2-en-1-one.

Authors:  Hoong-Kun Fun; Madhukar Hemamalini; S Samshuddin; B Narayana; B K Sarojini
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-16

3.  1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)ethanone.

Authors:  Hoong-Kun Fun; Madhukar Hemamalini; S Samshuddin; B Narayana; B K Sarojini
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-17

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  2 in total

1.  (E)-3-(3,5-Dimeth-oxy-phen-yl)-1-(2-meth-oxy-phen-yl)prop-2-en-1-one.

Authors:  Yoongho Lim; Dongsoo Koh
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-03-09

2.  (2E)-3-(4-Bromo-phen-yl)-1-(4,4''-difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one.

Authors:  Seranthimata Samshuddin; Badiadka Narayana; Hemmige S Yathirajan; Thomas Gerber; Eric Hosten; Richard Betz
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-24
  2 in total

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