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The mol­ecular geometry of the title compound, C15H8BrCl2FO, is stabilized by a C—H...Br inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016145/bt2321sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016145/bt2321Isup2.hkl
Contains datablock I

CCDC reference: 646757

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.030
  • wR factor = 0.077
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. F1 .. 3.17 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.98 From the CIF: _reflns_number_total 3234 Count of symmetry unique reflns 1773 Completeness (_total/calc) 182.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1461 Fraction of Friedel pairs measured 0.824 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-Bromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one top
Crystal data top
C15H8BrCl2FOF(000) = 368
Mr = 374.02Dx = 1.700 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 2547 reflections
a = 6.5423 (8) Åθ = 7–24°
b = 14.3317 (16) ŵ = 3.18 mm1
c = 7.8040 (9) ÅT = 293 K
β = 93.284 (2)°Block, colourless
V = 730.52 (15) Å30.23 × 0.22 × 0.21 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 28.0°, θmin = 3.0°
ω scansh = 88
7433 measured reflectionsk = 1818
3234 independent reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
3234 reflectionsΔρmax = 0.27 e Å3
182 parametersΔρmin = 0.45 e Å3
2 restraintsAbsolute structure: Flack (1983), 1526 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.049 (9)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.1716 (4)0.8902 (2)1.2368 (4)0.0479 (6)
H110.16800.91001.12320.058*
C140.1783 (5)0.8324 (2)1.5753 (4)0.0572 (7)
H140.18200.81371.68960.069*
C60.7765 (4)0.68072 (19)1.0157 (3)0.0390 (5)
O10.8629 (4)0.82168 (18)0.8876 (4)0.0697 (7)
Br10.51893 (6)0.949618 (19)0.96276 (6)0.06318 (12)
Cl10.41476 (13)0.64533 (7)0.84447 (12)0.0693 (2)
Cl20.9229 (2)0.37594 (7)1.08241 (14)0.0858 (3)
C100.3316 (4)0.83416 (17)1.3012 (3)0.0388 (5)
C90.4953 (4)0.79877 (18)1.1989 (3)0.0408 (5)
H90.55010.74211.23700.049*
C70.7464 (4)0.7827 (2)0.9782 (3)0.0426 (5)
C80.5797 (4)0.83285 (17)1.0616 (3)0.0387 (5)
C30.8614 (6)0.4926 (2)1.0589 (4)0.0579 (8)
C40.9998 (6)0.5590 (2)1.1188 (5)0.0624 (9)
C20.6812 (5)0.5191 (2)0.9783 (4)0.0537 (7)
H20.58740.47450.93750.064*
C150.3309 (5)0.8054 (2)1.4729 (4)0.0509 (6)
H150.43580.76731.51800.061*
C130.0205 (5)0.8868 (2)1.5099 (4)0.0540 (7)
H130.08480.90381.57870.065*
C10.6383 (4)0.6134 (2)0.9575 (4)0.0447 (6)
F11.1777 (5)0.5336 (2)1.1997 (5)0.1045 (10)
C50.9604 (5)0.6528 (2)1.0979 (4)0.0558 (7)
H51.05570.69691.13830.067*
C120.0183 (5)0.9164 (3)1.3409 (5)0.0564 (7)
H120.08760.95431.29720.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0504 (14)0.0470 (16)0.0471 (13)0.0019 (12)0.0094 (11)0.0025 (12)
C140.0716 (19)0.0533 (17)0.0486 (15)0.0015 (14)0.0205 (14)0.0018 (13)
C60.0406 (12)0.0387 (13)0.0388 (12)0.0016 (10)0.0108 (9)0.0022 (10)
O10.0774 (15)0.0575 (14)0.0789 (14)0.0051 (12)0.0448 (12)0.0197 (11)
Br10.06733 (18)0.04129 (15)0.0833 (2)0.00997 (14)0.02486 (14)0.02542 (15)
Cl10.0586 (4)0.0580 (5)0.0882 (6)0.0009 (4)0.0211 (4)0.0003 (4)
Cl20.1233 (9)0.0457 (4)0.0902 (6)0.0313 (5)0.0229 (6)0.0158 (4)
C100.0458 (12)0.0298 (11)0.0414 (12)0.0039 (9)0.0079 (10)0.0018 (9)
C90.0479 (13)0.0297 (12)0.0455 (12)0.0012 (10)0.0083 (10)0.0011 (10)
C70.0467 (13)0.0414 (14)0.0404 (12)0.0022 (11)0.0080 (10)0.0044 (10)
C80.0443 (12)0.0269 (11)0.0455 (13)0.0025 (9)0.0073 (10)0.0026 (10)
C30.081 (2)0.0403 (16)0.0548 (16)0.0173 (15)0.0214 (15)0.0095 (14)
C40.0594 (18)0.061 (2)0.0660 (19)0.0221 (16)0.0001 (15)0.0099 (16)
C20.0682 (18)0.0393 (15)0.0543 (15)0.0012 (13)0.0105 (13)0.0001 (12)
C150.0593 (16)0.0415 (15)0.0535 (14)0.0029 (13)0.0173 (12)0.0086 (12)
C130.0552 (15)0.0474 (15)0.0621 (18)0.0035 (13)0.0272 (15)0.0078 (12)
C10.0452 (14)0.0420 (15)0.0470 (14)0.0078 (11)0.0042 (11)0.0067 (11)
F10.0829 (17)0.0878 (18)0.139 (3)0.0380 (14)0.0305 (17)0.0170 (18)
C50.0523 (15)0.0499 (17)0.0652 (18)0.0065 (13)0.0020 (13)0.0029 (14)
C120.0484 (16)0.0513 (17)0.0704 (19)0.0063 (13)0.0119 (13)0.0014 (15)
Geometric parameters (Å, º) top
C11—C121.379 (4)C9—C81.326 (4)
C11—C101.390 (4)C9—H90.9300
C11—H110.9300C7—C81.487 (4)
C14—C131.369 (5)C3—C21.358 (5)
C14—C151.370 (4)C3—C41.377 (6)
C14—H140.9300C4—F11.342 (4)
C6—C11.381 (4)C4—C51.377 (5)
C6—C51.390 (4)C2—C11.388 (4)
C6—C71.502 (4)C2—H20.9300
O1—C71.206 (4)C15—H150.9300
Br1—C81.876 (2)C13—C121.384 (5)
Cl1—C11.726 (3)C13—H130.9300
Cl2—C31.727 (3)C5—H50.9300
C10—C151.403 (4)C12—H120.9300
C10—C91.463 (4)
C12—C11—C10120.1 (3)C4—C3—Cl2119.3 (3)
C12—C11—H11119.9F1—C4—C3120.6 (3)
C10—C11—H11119.9F1—C4—C5118.1 (4)
C13—C14—C15120.2 (3)C3—C4—C5121.3 (3)
C13—C14—H14119.9C3—C2—C1119.4 (3)
C15—C14—H14119.9C3—C2—H2120.3
C1—C6—C5119.0 (3)C1—C2—H2120.3
C1—C6—C7122.7 (2)C14—C15—C10121.1 (3)
C5—C6—C7118.1 (2)C14—C15—H15119.5
C11—C10—C15118.2 (2)C10—C15—H15119.5
C11—C10—C9124.2 (2)C14—C13—C12119.7 (3)
C15—C10—C9117.5 (2)C14—C13—H13120.1
C8—C9—C10131.7 (2)C12—C13—H13120.1
C8—C9—H9114.2C6—C1—C2121.1 (3)
C10—C9—H9114.2C6—C1—Cl1120.2 (2)
O1—C7—C8122.5 (3)C2—C1—Cl1118.5 (2)
O1—C7—C6119.0 (2)C4—C5—C6119.1 (3)
C8—C7—C6118.5 (2)C4—C5—H5120.4
C9—C8—C7121.7 (2)C6—C5—H5120.4
C9—C8—Br1124.9 (2)C11—C12—C13120.7 (3)
C7—C8—Br1113.3 (2)C11—C12—H12119.7
C2—C3—C4120.0 (3)C13—C12—H12119.7
C2—C3—Cl2120.7 (3)
C12—C11—C10—C150.3 (4)C4—C3—C2—C10.1 (5)
C12—C11—C10—C9176.7 (3)Cl2—C3—C2—C1178.3 (2)
C11—C10—C9—C829.2 (5)C13—C14—C15—C101.4 (5)
C15—C10—C9—C8154.4 (3)C11—C10—C15—C140.7 (4)
C1—C6—C7—O1113.4 (3)C9—C10—C15—C14177.4 (3)
C5—C6—C7—O160.2 (4)C15—C14—C13—C121.6 (5)
C1—C6—C7—C869.6 (3)C5—C6—C1—C20.6 (4)
C5—C6—C7—C8116.8 (3)C7—C6—C1—C2172.9 (3)
C10—C9—C8—C7179.6 (3)C5—C6—C1—Cl1176.4 (2)
C10—C9—C8—Br14.9 (4)C7—C6—C1—Cl12.9 (3)
O1—C7—C8—C9158.6 (3)C3—C2—C1—C60.6 (4)
C6—C7—C8—C918.3 (4)C3—C2—C1—Cl1176.5 (2)
O1—C7—C8—Br117.4 (4)F1—C4—C5—C6179.5 (3)
C6—C7—C8—Br1165.8 (2)C3—C4—C5—C60.5 (6)
C2—C3—C4—F1179.5 (4)C1—C6—C5—C40.1 (5)
Cl2—C3—C4—F12.2 (5)C7—C6—C5—C4173.8 (3)
C2—C3—C4—C50.5 (5)C10—C11—C12—C130.5 (5)
Cl2—C3—C4—C5177.8 (3)C14—C13—C12—C111.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Br10.932.743.319 (3)122
 

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