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In the title compound, C12H6Cl5O2, the dihedral angle between the two rings is 37°. This dihedral angle is different from the calculated dihedral angle in aqueous solution (48°), a likely cause being the influence of crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200291X/om6077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680200291X/om6077Isup2.hkl
Contains datablock I

CCDC reference: 183779

Key indicators

  • Single-crystal X-ray study
  • T = 145 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.083
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

(I) top
Crystal data top
C12H6Cl2O2F(000) = 512
Mr = 253.07Dx = 1.560 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.1344 (14) ÅCell parameters from 40323 reflections
b = 6.6257 (5) Åθ = 1.0–27.5°
c = 9.0173 (7) ŵ = 0.58 mm1
β = 95.903 (3)°T = 145 K
V = 1077.7 (2) Å3Irregular plate, orange
Z = 40.40 × 0.25 × 0.01 mm
Data collection top
Nonius KappaCCD
diffractometer
1891 independent reflections
Radiation source: fine-focus sealed tube1427 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 18 pixels mm-1θmax = 25.0°, θmin = 1.1°
ω scans at fixed χ = 55°h = 2121
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 77
Tmin = 0.801, Tmax = 0.994l = 1010
3600 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.02P)2 + 0.2379P]
where P = (Fo2 + 2Fc2)/3
1891 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.31 e Å3
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
Cl10.45935 (4)0.36703 (12)0.81570 (9)0.0502 (3)
Cl20.33327 (4)0.30371 (11)1.00676 (8)0.0436 (3)
O10.18664 (10)0.5221 (3)0.6691 (2)0.0357 (5)
O20.05463 (10)0.0982 (3)0.3810 (2)0.0357 (5)
C10.18888 (13)0.1694 (4)0.6231 (3)0.0203 (6)
C20.16094 (14)0.3790 (4)0.5956 (3)0.0246 (7)
C30.09868 (14)0.4080 (4)0.4779 (3)0.0305 (7)
H30.08310.54150.45210.037*
C40.06401 (14)0.2553 (4)0.4076 (3)0.0289 (7)
H40.02370.28020.33400.035*
C50.08741 (14)0.0463 (4)0.4426 (3)0.0261 (7)
C60.15238 (13)0.0167 (4)0.5513 (3)0.0241 (7)
H60.16940.11700.57180.029*
C70.25635 (13)0.1333 (4)0.7274 (3)0.0206 (6)
C80.31748 (14)0.2620 (4)0.7318 (3)0.0273 (7)
H80.31430.38450.67680.033*
C90.38249 (14)0.2104 (4)0.8164 (3)0.0288 (7)
C100.38839 (15)0.0370 (4)0.9011 (3)0.0314 (7)
H100.43340.00340.95930.038*
C110.32717 (15)0.0864 (4)0.8988 (3)0.0265 (7)
C120.26167 (14)0.0409 (4)0.8136 (3)0.0226 (6)
H120.22020.12870.81390.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0281 (5)0.0586 (6)0.0628 (6)0.0171 (4)0.0013 (4)0.0009 (4)
Cl20.0409 (5)0.0472 (5)0.0410 (5)0.0064 (4)0.0041 (4)0.0202 (4)
O10.0403 (12)0.0208 (11)0.0449 (13)0.0008 (9)0.0008 (10)0.0051 (10)
O20.0344 (12)0.0313 (12)0.0382 (13)0.0042 (10)0.0120 (9)0.0030 (10)
C10.0211 (15)0.0185 (16)0.0213 (16)0.0004 (12)0.0026 (12)0.0019 (12)
C20.0250 (16)0.0203 (16)0.0294 (17)0.0009 (13)0.0067 (13)0.0032 (14)
C30.0272 (16)0.0214 (17)0.0425 (19)0.0052 (14)0.0014 (14)0.0076 (15)
C40.0233 (15)0.0318 (18)0.0300 (17)0.0035 (14)0.0048 (13)0.0078 (14)
C50.0232 (16)0.0303 (18)0.0242 (17)0.0027 (14)0.0006 (13)0.0013 (14)
C60.0260 (16)0.0204 (16)0.0250 (17)0.0021 (13)0.0023 (13)0.0034 (13)
C70.0270 (16)0.0179 (15)0.0172 (15)0.0002 (13)0.0032 (12)0.0023 (12)
C80.0276 (17)0.0228 (16)0.0313 (17)0.0021 (14)0.0025 (14)0.0002 (13)
C90.0237 (16)0.0320 (18)0.0303 (17)0.0100 (13)0.0017 (13)0.0068 (15)
C100.0211 (16)0.046 (2)0.0258 (17)0.0039 (15)0.0045 (13)0.0010 (15)
C110.0296 (17)0.0308 (17)0.0191 (16)0.0025 (14)0.0022 (13)0.0005 (13)
C120.0223 (15)0.0220 (16)0.0229 (16)0.0020 (12)0.0000 (13)0.0038 (13)
Geometric parameters (Å, º) top
Cl1—C91.738 (3)C5—C61.466 (3)
Cl2—C111.735 (3)C6—H60.9500
O1—C21.221 (3)C7—C121.390 (3)
O2—C51.229 (3)C7—C81.396 (3)
C1—C61.339 (3)C8—C91.380 (3)
C1—C71.484 (3)C8—H80.9500
C1—C21.490 (3)C9—C101.377 (3)
C2—C31.480 (4)C10—C111.377 (4)
C3—C41.319 (4)C10—H100.9500
C3—H30.9500C11—C121.380 (3)
C4—C51.473 (4)C12—H120.9500
C4—H40.9500
C6—C1—C7121.3 (2)C12—C7—C8118.8 (2)
C6—C1—C2118.8 (2)C12—C7—C1119.6 (2)
C7—C1—C2120.0 (2)C8—C7—C1121.3 (2)
O1—C2—C3120.6 (2)C9—C8—C7119.7 (2)
O1—C2—C1121.9 (2)C9—C8—H8120.2
C3—C2—C1117.5 (2)C7—C8—H8120.2
C4—C3—C2122.4 (2)C10—C9—C8121.8 (2)
C4—C3—H3118.8C10—C9—Cl1118.9 (2)
C2—C3—H3118.8C8—C9—Cl1119.3 (2)
C3—C4—C5120.4 (2)C11—C10—C9118.0 (2)
C3—C4—H4119.8C11—C10—H10121.0
C5—C4—H4119.8C9—C10—H10121.0
O2—C5—C6121.1 (2)C10—C11—C12121.7 (2)
O2—C5—C4121.3 (2)C10—C11—Cl2118.6 (2)
C6—C5—C4117.6 (2)C12—C11—Cl2119.7 (2)
C1—C6—C5123.1 (2)C11—C12—C7119.9 (2)
C1—C6—H6118.5C11—C12—H12120.0
C5—C6—H6118.5C7—C12—H12120.0
C6—C1—C2—O1171.9 (2)C6—C1—C7—C8139.7 (3)
C7—C1—C2—O18.6 (4)C2—C1—C7—C839.8 (3)
C6—C1—C2—C36.3 (3)C12—C7—C8—C92.5 (4)
C7—C1—C2—C3173.2 (2)C1—C7—C8—C9171.9 (2)
O1—C2—C3—C4172.3 (3)C7—C8—C9—C101.9 (4)
C1—C2—C3—C45.9 (4)C7—C8—C9—Cl1177.63 (19)
C2—C3—C4—C51.2 (4)C8—C9—C10—C110.4 (4)
C3—C4—C5—O2178.1 (3)Cl1—C9—C10—C11179.2 (2)
C3—C4—C5—C63.2 (4)C9—C10—C11—C120.7 (4)
C7—C1—C6—C5177.3 (2)C9—C10—C11—Cl2179.1 (2)
C2—C1—C6—C52.2 (4)C10—C11—C12—C70.1 (4)
O2—C5—C6—C1178.7 (2)Cl2—C11—C12—C7179.72 (18)
C4—C5—C6—C12.6 (4)C8—C7—C12—C111.5 (4)
C6—C1—C7—C1234.7 (3)C1—C7—C12—C11173.0 (2)
C2—C1—C7—C12145.8 (2)
 

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