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The dihedral angle between the benzene rings in the title compound, C12H7Cl3, is 47.25 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020975/bt6503sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020975/bt6503Isup2.hkl
Contains datablock I

CCDC reference: 251761

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.063
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

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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 Siemens SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local programs.

2,4,5-Trichlorobiphenyl top
Crystal data top
C12H7Cl3Z = 2
Mr = 257.53F(000) = 260
Triclinic, P1Dx = 1.612 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.8501 (1) ÅCell parameters from 2350 reflections
b = 11.4482 (3) Åθ = 1.0–27.5°
c = 13.0504 (3) ŵ = 0.82 mm1
α = 109.8409 (10)°T = 90 K
β = 92.9891 (9)°Block, colourless
γ = 99.2004 (10)°0.24 × 0.15 × 0.10 mm
V = 530.59 (2) Å3
Data collection top
Nonius KappaCCD
diffractometer
2383 independent reflections
Radiation source: fine-focus sealed tube2065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 18 pixels mm-1θmax = 27.4°, θmin = 1.7°
ω scans at fixed χ = 55°h = 44
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1414
Tmin = 0.827, Tmax = 0.923l = 1616
4668 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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0219P)2 + 0.2643P]
where P = (Fo2 + 2Fc2)/3
2383 reflections(Δ/σ)max = 0.001
136 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.23 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
Cl10.80966 (9)0.83122 (3)0.46829 (3)0.01575 (10)
Cl20.05951 (10)0.36169 (3)0.34530 (3)0.02002 (11)
Cl30.13183 (10)0.36458 (3)0.10681 (3)0.01658 (10)
C10.4488 (4)0.71178 (13)0.26217 (12)0.0123 (3)
C20.5374 (4)0.70580 (13)0.36535 (12)0.0127 (3)
C30.4194 (4)0.59877 (13)0.39064 (12)0.0142 (3)
H30.48160.59780.46170.017*
C40.2102 (4)0.49321 (14)0.31170 (12)0.0140 (3)
C50.1246 (4)0.49499 (13)0.20769 (12)0.0129 (3)
C60.2426 (4)0.60282 (13)0.18410 (12)0.0132 (3)
H60.18160.60290.11260.016*
C1'0.5523 (4)0.82519 (13)0.23063 (12)0.0117 (3)
C2'0.5000 (4)0.94448 (14)0.29679 (12)0.0155 (3)
H2'0.41520.95560.36590.019*
C3'0.5716 (4)1.04634 (14)0.26171 (13)0.0179 (3)
H3'0.53521.12710.30700.021*
C4'0.6960 (4)1.03155 (15)0.16099 (13)0.0190 (3)
H4'0.74581.10190.13750.023*
C5'0.7473 (4)0.91324 (15)0.09469 (13)0.0181 (3)
H5'0.83140.90240.02550.022*
C6'0.6757 (4)0.81087 (14)0.12939 (12)0.0150 (3)
H6'0.71120.73020.08370.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01671 (18)0.01394 (18)0.01285 (17)0.00007 (13)0.00104 (13)0.00169 (13)
Cl20.0240 (2)0.01614 (19)0.0200 (2)0.00256 (15)0.00216 (15)0.01001 (15)
Cl30.01878 (19)0.01301 (18)0.01416 (18)0.00050 (13)0.00160 (13)0.00205 (14)
C10.0106 (7)0.0133 (7)0.0137 (7)0.0046 (5)0.0035 (5)0.0042 (6)
C20.0106 (7)0.0122 (7)0.0125 (7)0.0026 (5)0.0014 (5)0.0004 (6)
C30.0136 (7)0.0168 (7)0.0127 (7)0.0043 (6)0.0016 (5)0.0053 (6)
C40.0139 (7)0.0128 (7)0.0168 (7)0.0028 (6)0.0023 (6)0.0069 (6)
C50.0112 (7)0.0111 (7)0.0136 (7)0.0025 (5)0.0006 (5)0.0008 (6)
C60.0132 (7)0.0149 (7)0.0115 (7)0.0044 (6)0.0018 (5)0.0038 (6)
C1'0.0102 (7)0.0114 (7)0.0132 (7)0.0016 (5)0.0010 (5)0.0044 (6)
C2'0.0137 (7)0.0157 (7)0.0160 (7)0.0021 (6)0.0026 (6)0.0045 (6)
C3'0.0173 (8)0.0136 (7)0.0212 (8)0.0025 (6)0.0005 (6)0.0047 (6)
C4'0.0178 (8)0.0180 (8)0.0230 (8)0.0004 (6)0.0001 (6)0.0116 (6)
C5'0.0163 (8)0.0226 (8)0.0160 (7)0.0010 (6)0.0013 (6)0.0091 (6)
C6'0.0135 (7)0.0152 (7)0.0150 (7)0.0025 (6)0.0003 (6)0.0037 (6)
Geometric parameters (Å, º) top
Cl1—C21.7399 (14)C1'—C6'1.393 (2)
Cl2—C41.7295 (15)C1'—C2'1.399 (2)
Cl3—C51.7309 (14)C2'—C3'1.385 (2)
C1—C21.399 (2)C2'—H2'0.9500
C1—C61.400 (2)C3'—C4'1.388 (2)
C1—C1'1.4928 (19)C3'—H3'0.9500
C2—C31.389 (2)C4'—C5'1.389 (2)
C3—C41.388 (2)C4'—H4'0.9500
C3—H30.9500C5'—C6'1.387 (2)
C4—C51.388 (2)C5'—H5'0.9500
C5—C61.385 (2)C6'—H6'0.9500
C6—H60.9500
C2—C1—C6116.63 (13)C6'—C1'—C2'118.97 (13)
C2—C1—C1'124.99 (13)C6'—C1'—C1119.65 (13)
C6—C1—C1'118.37 (13)C2'—C1'—C1121.15 (13)
C3—C2—C1121.98 (13)C3'—C2'—C1'120.13 (14)
C3—C2—Cl1116.30 (11)C3'—C2'—H2'119.9
C1—C2—Cl1121.70 (11)C1'—C2'—H2'119.9
C4—C3—C2119.77 (13)C2'—C3'—C4'120.60 (14)
C4—C3—H3120.1C2'—C3'—H3'119.7
C2—C3—H3120.1C4'—C3'—H3'119.7
C5—C4—C3119.67 (13)C3'—C4'—C5'119.56 (14)
C5—C4—Cl2121.18 (11)C3'—C4'—H4'120.2
C3—C4—Cl2119.15 (11)C5'—C4'—H4'120.2
C6—C5—C4119.78 (13)C6'—C5'—C4'120.07 (14)
C6—C5—Cl3119.26 (11)C6'—C5'—H5'120.0
C4—C5—Cl3120.95 (11)C4'—C5'—H5'120.0
C5—C6—C1122.13 (13)C5'—C6'—C1'120.66 (14)
C5—C6—H6118.9C5'—C6'—H6'119.7
C1—C6—H6118.9C1'—C6'—H6'119.7
C6—C1—C2—C31.8 (2)C2—C1—C6—C51.3 (2)
C1'—C1—C2—C3177.18 (14)C1'—C1—C6—C5177.70 (13)
C6—C1—C2—Cl1176.89 (11)C2—C1—C1'—C6'136.37 (15)
C1'—C1—C2—Cl14.2 (2)C6—C1—C1'—C6'44.69 (19)
C1—C2—C3—C40.7 (2)C2—C1—C1'—C2'49.1 (2)
Cl1—C2—C3—C4178.00 (11)C6—C1—C1'—C2'129.87 (15)
C2—C3—C4—C50.8 (2)C6'—C1'—C2'—C3'0.2 (2)
C2—C3—C4—Cl2178.94 (11)C1—C1'—C2'—C3'174.82 (13)
C3—C4—C5—C61.3 (2)C1'—C2'—C3'—C4'0.1 (2)
Cl2—C4—C5—C6178.51 (11)C2'—C3'—C4'—C5'0.3 (2)
C3—C4—C5—Cl3179.33 (11)C3'—C4'—C5'—C6'0.3 (2)
Cl2—C4—C5—Cl30.89 (19)C4'—C5'—C6'—C1'0.0 (2)
C4—C5—C6—C10.2 (2)C2'—C1'—C6'—C5'0.3 (2)
Cl3—C5—C6—C1179.57 (11)C1—C1'—C6'—C5'174.96 (13)
 

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