Literature DB >> 21202561

2,3-Dibromo-1-(2,4-dichloro-5-fluoro-phen-yl)-3-phenyl-propan-1-one.

Hoong-Kun Fun, Samuel Robinson Jebas, Ibrahim Abdul Razak, M S Karthikeyan, P S Patil, S M Dharmaprakash.   

Abstract

In the title compound, C(15)H(9)Br(2)Cl(2)FO, the dihedral angle between the two aromatic rings is 6.0 (1)°. The dibromo-ethane fragment of the propan-1-one unit is disordered over two positions, with occupancies of ca 0.83 and 0.17. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds, C-H⋯π inter-actions, and Br⋯Cl [3.505 (2) and 3.576 (6) Å] and Cl⋯F [3.176 (2) Å] short contacts.

Entities:  

Year:  2008        PMID： 21202561      PMCID： PMC2961431          DOI： 10.1107/S1600536808013238

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


Related literature

For related literature, see: Agrinskaya et al. (1999 ▶); Patil et al. (2006 ▶); John Kiran et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the preparation, see: Shivarama Holla et al. 2006 ▶).

Experimental

Crystal data

C15H9Br2Cl2FO M = 454.94 Orthorhombic, a = 7.1232 (1) Å b = 10.0757 (2) Å c = 43.0262 (7) Å V = 3088.04 (9) Å3 Z = 8 Mo Kα radiation μ = 5.60 mm−1 T = 100 (2) K 0.40 × 0.24 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.211, T max = 0.508 (expected range = 0.190–0.457) 26343 measured reflections 5857 independent reflections 3681 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.089 S = 0.98 5857 reflections 227 parameters 60 restraints H-atom parameters constrained Δρmax = 0.77 e Å−3 Δρmin = −0.76 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013238/ci2588sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013238/ci2588Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H9Br2Cl2FOF000 = 1760
Mr = 454.94Dx = 1.957 Mg m−3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4782 reflections
a = 7.1232 (1) Åθ = 2.8–28.1º
b = 10.0757 (2) ŵ = 5.60 mm−1
c = 43.0262 (7) ÅT = 100 (2) K
V = 3088.04 (9) Å3Block, colourless
Z = 80.40 × 0.24 × 0.14 mm
Bruker SMART APEXII CCD area-detector diffractometer5857 independent reflections
Radiation source: fine-focus sealed tube3681 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.056
T = 100(2) Kθmax = 33.2º
φ and ω scansθmin = 1.0º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −10→8
Tmin = 0.211, Tmax = 0.508k = −15→15
26343 measured reflectionsl = −52→66
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.089  w = 1/[σ2(Fo2) + (0.0309P)2 + 2.3603P] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
5857 reflectionsΔρmax = 0.77 e Å−3
227 parametersΔρmin = −0.76 e Å−3
60 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Experimental. The data was collected with the Oxford Cyrosystem Cobra low–temperature attachment.
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*/UeqOcc. (<1)
Cl10.58123 (10)0.31692 (7)−0.003788 (15)0.02739 (16)
Cl20.62659 (10)−0.10513 (7)0.070833 (16)0.02701 (16)
F10.3512 (3)0.42768 (15)0.04559 (4)0.0314 (4)
O10.3888 (3)−0.05963 (18)0.12256 (4)0.0211 (4)
C10.0038 (4)0.0604 (3)0.21381 (6)0.0229 (6)
H10.0475−0.02860.21510.028*
C2−0.0915 (4)0.1152 (3)0.23859 (6)0.0243 (6)
H2−0.11470.06350.25670.029*
C3−0.1533 (4)0.2449 (3)0.23723 (7)0.0273 (6)
H3−0.21970.28220.25430.033*
C4−0.1181 (4)0.3209 (3)0.21087 (7)0.0260 (6)
H4−0.15810.41070.21000.031*
C5−0.0250 (5)0.2651 (3)0.18597 (7)0.0290 (7)
H5−0.00250.31660.16790.035*
C60.0365 (4)0.1337 (3)0.18715 (6)0.0265 (6)
C90.3635 (4)0.0567 (3)0.11688 (6)0.0189 (5)
C100.4255 (4)0.1189 (2)0.08738 (6)0.0176 (5)
C110.3646 (4)0.2472 (3)0.07982 (6)0.0222 (6)
H110.28830.29490.09410.027*
C120.4138 (4)0.3047 (3)0.05211 (6)0.0216 (6)
C130.5258 (4)0.2405 (3)0.03074 (6)0.0196 (5)
C140.5896 (4)0.1134 (3)0.03752 (6)0.0203 (5)
H140.66730.06770.02310.024*
C150.5397 (4)0.0535 (2)0.06529 (6)0.0185 (5)
Br10.4779 (3)0.1813 (3)0.17334 (5)0.0279 (4)0.834 (6)
Br2−0.06956 (14)0.02708 (17)0.12693 (3)0.0296 (2)0.834 (6)
C70.1226 (5)0.0653 (3)0.15969 (7)0.0194 (8)0.834 (6)
H70.1772−0.02090.16680.023*0.834 (6)
C80.2737 (5)0.1420 (4)0.14272 (7)0.0190 (8)0.834 (6)
H80.22160.22610.13390.023*0.834 (6)
Br1A−0.0440 (7)0.0638 (6)0.11951 (14)0.0265 (8)0.166 (6)
Br2A0.4743 (16)0.1862 (16)0.1704 (2)0.0222 (16)0.166 (6)
C7A0.2193 (14)0.0999 (16)0.1700 (3)0.028 (5)0.166 (6)
H7A0.24050.00250.17280.033*0.166 (6)
C8A0.2088 (11)0.1248 (14)0.1348 (3)0.015 (4)0.166 (6)
H8A0.21900.22250.13110.018*0.166 (6)
U11U22U33U12U13U23
Cl10.0264 (4)0.0359 (4)0.0198 (3)0.0014 (3)0.0055 (3)0.0042 (3)
Cl20.0290 (4)0.0221 (3)0.0300 (3)0.0083 (3)0.0061 (3)−0.0018 (3)
F10.0442 (11)0.0200 (8)0.0302 (9)0.0078 (8)0.0112 (8)0.0069 (7)
O10.0246 (11)0.0173 (9)0.0214 (9)0.0019 (8)−0.0011 (8)−0.0018 (7)
C10.0237 (15)0.0222 (13)0.0229 (13)−0.0004 (12)0.0020 (11)0.0000 (10)
C20.0224 (15)0.0293 (15)0.0212 (13)−0.0056 (12)0.0026 (11)0.0010 (11)
C30.0224 (16)0.0323 (16)0.0271 (15)−0.0049 (13)0.0061 (12)−0.0067 (12)
C40.0217 (15)0.0226 (14)0.0338 (15)0.0022 (12)0.0043 (12)−0.0038 (12)
C50.0381 (19)0.0219 (14)0.0270 (15)0.0049 (13)0.0102 (13)0.0045 (11)
C60.0322 (18)0.0248 (14)0.0226 (13)0.0052 (13)0.0082 (12)0.0013 (11)
C90.0190 (14)0.0173 (12)0.0203 (13)−0.0010 (11)0.0019 (10)−0.0016 (10)
C100.0183 (13)0.0148 (12)0.0198 (12)−0.0012 (10)0.0021 (10)−0.0022 (9)
C110.0250 (15)0.0176 (13)0.0239 (13)0.0009 (12)0.0051 (11)−0.0021 (10)
C120.0237 (14)0.0165 (12)0.0245 (13)−0.0004 (11)0.0011 (11)0.0019 (10)
C130.0182 (14)0.0249 (14)0.0158 (12)−0.0051 (11)0.0010 (10)−0.0012 (10)
C140.0171 (13)0.0245 (14)0.0192 (12)0.0008 (11)0.0025 (10)−0.0054 (10)
C150.0144 (13)0.0165 (12)0.0244 (13)−0.0008 (10)−0.0013 (10)−0.0034 (10)
Br10.0181 (5)0.0296 (5)0.0359 (9)−0.0023 (4)−0.0012 (5)−0.0105 (7)
Br20.0212 (3)0.0379 (5)0.0296 (4)−0.0013 (3)−0.0041 (3)−0.0111 (3)
C70.0208 (18)0.0182 (15)0.0191 (15)0.0007 (13)−0.0027 (13)−0.0016 (12)
C80.022 (2)0.0175 (16)0.0173 (17)−0.0011 (15)−0.0004 (15)−0.0024 (12)
Br1A0.0242 (14)0.0302 (17)0.0252 (16)−0.0071 (12)−0.0074 (11)0.0019 (12)
Br2A0.030 (3)0.031 (3)0.0061 (13)−0.008 (2)0.0041 (14)−0.0099 (13)
C7A0.027 (8)0.021 (7)0.035 (8)−0.010 (6)−0.010 (6)0.006 (6)
C8A0.015 (7)0.014 (7)0.016 (7)−0.005 (6)−0.007 (5)0.003 (5)
Cl1—C131.719 (3)C9—C81.544 (4)
Cl2—C151.731 (3)C10—C111.402 (4)
F1—C121.346 (3)C10—C151.414 (4)
O1—C91.211 (3)C11—C121.371 (4)
C1—C21.380 (4)C11—H110.95
C1—C61.384 (4)C12—C131.379 (4)
C1—H10.95C13—C141.390 (4)
C2—C31.380 (4)C14—C151.385 (4)
C2—H20.95C14—H140.95
C3—C41.391 (4)Br1—C82.002 (4)
C3—H30.95Br2—C72.002 (3)
C4—C51.380 (4)C7—C81.513 (4)
C4—H40.95C7—H71.00
C5—C61.395 (4)C8—H81.00
C5—H50.95Br1A—C8A2.013 (8)
C6—C71.499 (4)Br2A—C7A2.014 (8)
C6—C7A1.536 (9)C7A—C8A1.535 (9)
C9—C101.483 (4)C7A—H7A1.00
C9—C8A1.509 (9)C8A—H8A1.00
C2—C1—C6120.6 (3)C12—C13—C14118.8 (2)
C2—C1—H1119.7C12—C13—Cl1119.9 (2)
C6—C1—H1119.7C14—C13—Cl1121.3 (2)
C1—C2—C3120.2 (3)C15—C14—C13119.9 (2)
C1—C2—H2119.9C15—C14—H14120.0
C3—C2—H2119.9C13—C14—H14120.0
C2—C3—C4119.9 (3)C14—C15—C10121.6 (2)
C2—C3—H3120.1C14—C15—Cl2115.5 (2)
C4—C3—H3120.1C10—C15—Cl2122.9 (2)
C5—C4—C3119.7 (3)C6—C7—C8115.9 (3)
C5—C4—H4120.2C6—C7—Br2111.3 (2)
C3—C4—H4120.2C8—C7—Br2104.2 (2)
C4—C5—C6120.6 (3)C6—C7—H7108.4
C4—C5—H5119.7C8—C7—H7108.4
C6—C5—H5119.7Br2—C7—H7108.4
C1—C6—C5118.9 (3)C7—C8—C9110.9 (3)
C1—C6—C7118.5 (3)C7—C8—Br1107.5 (2)
C5—C6—C7122.4 (3)C9—C8—Br1106.5 (2)
C1—C6—C7A115.1 (6)C7—C8—H8110.6
C5—C6—C7A117.3 (6)C9—C8—H8110.6
O1—C9—C10122.5 (2)Br1—C8—H8110.6
O1—C9—C8A116.5 (6)C8A—C7A—C6113.4 (8)
C10—C9—C8A117.6 (6)C8A—C7A—Br2A89.1 (7)
O1—C9—C8117.1 (2)C6—C7A—Br2A131.6 (9)
C10—C9—C8120.3 (2)C8A—C7A—H7A106.7
C11—C10—C15116.9 (2)C6—C7A—H7A106.7
C11—C10—C9119.7 (2)Br2A—C7A—H7A106.7
C15—C10—C9123.4 (2)C9—C8A—C7A113.2 (8)
C12—C11—C10120.8 (2)C9—C8A—Br1A110.3 (6)
C12—C11—H11119.6C7A—C8A—Br1A108.4 (8)
C10—C11—H11119.6C9—C8A—H8A108.3
F1—C12—C11119.0 (2)C7A—C8A—H8A108.3
F1—C12—C13119.0 (2)Br1A—C8A—H8A108.3
C11—C12—C13122.0 (2)
C6—C1—C2—C3−0.9 (4)C1—C6—C7—C8−137.6 (3)
C1—C2—C3—C4−0.5 (4)C5—C6—C7—C847.5 (4)
C2—C3—C4—C51.3 (4)C7A—C6—C7—C8−44.3 (10)
C3—C4—C5—C6−0.9 (5)C1—C6—C7—Br2103.6 (3)
C2—C1—C6—C51.4 (5)C5—C6—C7—Br2−71.2 (4)
C2—C1—C6—C7−173.7 (3)C7A—C6—C7—Br2−163.1 (11)
C2—C1—C6—C7A148.2 (6)C6—C7—C8—C9174.9 (3)
C4—C5—C6—C1−0.5 (5)Br2—C7—C8—C9−62.5 (3)
C4—C5—C6—C7174.4 (3)C6—C7—C8—Br158.9 (3)
C4—C5—C6—C7A−146.6 (6)Br2—C7—C8—Br1−178.49 (17)
O1—C9—C10—C11169.1 (3)O1—C9—C8—C7−38.7 (4)
C8A—C9—C10—C1110.9 (5)C10—C9—C8—C7145.0 (3)
C8—C9—C10—C11−14.8 (4)C8A—C9—C8—C755.5 (16)
O1—C9—C10—C15−8.5 (4)O1—C9—C8—Br177.9 (3)
C8A—C9—C10—C15−166.7 (4)C10—C9—C8—Br1−98.3 (3)
C8—C9—C10—C15167.6 (3)C8A—C9—C8—Br1172.1 (18)
C15—C10—C11—C120.4 (4)C1—C6—C7A—C8A151.0 (9)
C9—C10—C11—C12−177.3 (3)C5—C6—C7A—C8A−61.6 (12)
C10—C11—C12—F1179.5 (2)C7—C6—C7A—C8A46.7 (9)
C10—C11—C12—C13−0.7 (4)C1—C6—C7A—Br2A−97.9 (12)
F1—C12—C13—C14−179.8 (2)C5—C6—C7A—Br2A49.5 (13)
C11—C12—C13—C140.3 (4)C7—C6—C7A—Br2A157.8 (19)
F1—C12—C13—Cl1−0.7 (4)O1—C9—C8A—C7A49.1 (10)
C11—C12—C13—Cl1179.4 (2)C10—C9—C8A—C7A−151.4 (8)
C12—C13—C14—C150.3 (4)C8—C9—C8A—C7A−48.3 (12)
Cl1—C13—C14—C15−178.8 (2)O1—C9—C8A—Br1A−72.6 (8)
C13—C14—C15—C10−0.5 (4)C10—C9—C8A—Br1A86.9 (8)
C13—C14—C15—Cl2179.5 (2)C8—C9—C8A—Br1A−170 (2)
C11—C10—C15—C140.2 (4)C6—C7A—C8A—C9−163.6 (8)
C9—C10—C15—C14177.8 (3)Br2A—C7A—C8A—C960.7 (10)
C11—C10—C15—Cl2−179.9 (2)C6—C7A—C8A—Br1A−40.8 (13)
C9—C10—C15—Cl2−2.2 (4)Br2A—C7A—C8A—Br1A−176.6 (8)
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.952.453.392 (4)170
C8—H8···O1i1.002.353.336 (4)169
C11—H11···O1i0.952.293.229 (3)170
C3—H3···Cg1ii0.952.963.652 (3)131
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C5—H5⋯O1i0.952.453.392 (4)170
C8—H8⋯O1i1.002.353.336 (4)169
C11—H11⋯O1i0.952.293.229 (3)170
C3—H3⋯Cg1ii0.952.963.652 (3)131

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1–C6 benzene ring.

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