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The title compound, C6H2BrCl2I, crystallizes in space group P21/c with two mol­ecules in the asymmetric unit. The mol­ecules stack in two different directions, with their plane normals approximately parallel to [110] and [1\overline 10]. The mol­ecules of the asymmetric unit are held together by π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402392X/wn6282sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680402392X/wn6282Isup2.hkl
Contains datablock I

CCDC reference: 231991

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.057
  • wR factor = 0.147
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.18 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. Cl4 .. 3.44 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.180 Tmax scaled 0.180 Tmin scaled 0.065
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 in WinGX (Farrugia, 1999); program(s) used to solve structure: SIR92 in WinGX; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX; software used to prepare material for publication: SHELXL97.

5-Bromo-1,3-dichloro-2-iodobenzene top
Crystal data top
C6H2BrCl2IF(000) = 1280
Mr = 351.79Dx = 2.616 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.630 (6) ÅCell parameters from 25 reflections
b = 10.020 (4) Åθ = 10–15°
c = 16.30 (1) ŵ = 8.58 mm1
β = 109.84 (4)°T = 293 K
V = 1786.6 (15) Å3Block, colourless
Z = 80.3 × 0.2 × 0.2 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1730 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω/2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.361, Tmax = 1.000l = 1918
3287 measured reflections2 standard reflections every 60 min
3125 independent reflections intensity decay: none
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0856P)2]
where P = (Fo2 + 2Fc2)/3
3125 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 1.16 e Å3
0 restraintsΔρmin = 1.71 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
C10.8819 (9)0.4265 (11)0.0461 (6)0.041 (2)
C20.7979 (10)0.4264 (11)0.0398 (7)0.046 (3)
C30.7926 (9)0.3288 (12)0.1006 (6)0.045 (3)
H30.73520.33220.15650.054*
C40.8744 (10)0.2277 (11)0.0756 (6)0.044 (3)
C50.9634 (10)0.2177 (11)0.0108 (6)0.046 (3)
H51.01870.14740.02720.055*
C60.9614 (9)0.3206 (11)0.0689 (6)0.040 (2)
C70.6534 (10)0.1141 (11)0.0394 (6)0.044 (3)
C80.5940 (10)0.2355 (11)0.0348 (6)0.043 (3)
C90.5155 (9)0.2916 (11)0.0437 (6)0.046 (3)
H90.47710.37340.04510.055*
C100.4989 (9)0.2165 (12)0.1196 (6)0.046 (3)
C110.5557 (10)0.0959 (10)0.1175 (6)0.046 (3)
H110.54170.04760.16870.055*
C120.6336 (9)0.0462 (12)0.0393 (7)0.050 (3)
Cl10.6927 (3)0.5573 (3)0.0744 (2)0.0691 (9)
Cl21.0719 (3)0.3062 (4)0.17239 (17)0.0725 (10)
Cl30.6131 (3)0.3298 (4)0.12813 (17)0.0712 (10)
Cl40.7030 (3)0.1032 (3)0.0396 (2)0.0707 (9)
Br10.87679 (14)0.09778 (14)0.15729 (8)0.0699 (4)
Br20.39898 (13)0.28920 (16)0.22700 (7)0.0710 (4)
I10.88694 (9)0.57855 (9)0.13488 (5)0.0670 (3)
I20.77746 (8)0.04638 (10)0.15695 (5)0.0660 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.028 (5)0.046 (7)0.054 (5)0.004 (6)0.020 (4)0.004 (5)
C20.041 (6)0.046 (7)0.058 (6)0.006 (6)0.026 (5)0.012 (5)
C30.039 (6)0.055 (8)0.043 (5)0.002 (6)0.016 (4)0.000 (5)
C40.041 (6)0.046 (7)0.054 (5)0.009 (6)0.028 (5)0.007 (5)
C50.042 (6)0.042 (7)0.053 (5)0.006 (6)0.017 (5)0.006 (5)
C60.036 (6)0.038 (7)0.047 (5)0.012 (6)0.015 (4)0.003 (5)
C70.046 (6)0.043 (7)0.048 (5)0.020 (6)0.021 (4)0.004 (5)
C80.039 (6)0.049 (7)0.045 (5)0.003 (6)0.020 (4)0.002 (5)
C90.031 (6)0.045 (7)0.059 (6)0.003 (6)0.013 (4)0.001 (5)
C100.029 (5)0.062 (8)0.043 (5)0.002 (6)0.008 (4)0.005 (5)
C110.063 (7)0.026 (6)0.052 (5)0.000 (6)0.024 (5)0.002 (5)
C120.033 (6)0.052 (8)0.070 (6)0.017 (6)0.026 (5)0.002 (6)
Cl10.061 (2)0.054 (2)0.092 (2)0.0225 (19)0.0263 (16)0.0166 (16)
Cl20.065 (2)0.083 (3)0.0545 (14)0.006 (2)0.0016 (13)0.0019 (15)
Cl30.068 (2)0.088 (3)0.0533 (14)0.012 (2)0.0147 (14)0.0186 (16)
Cl40.074 (2)0.049 (2)0.092 (2)0.012 (2)0.0319 (17)0.0021 (16)
Br10.0833 (10)0.0660 (9)0.0656 (7)0.0118 (8)0.0322 (6)0.0118 (6)
Br20.0664 (8)0.0870 (11)0.0512 (6)0.0069 (8)0.0088 (5)0.0082 (6)
I10.0860 (7)0.0553 (5)0.0739 (5)0.0146 (5)0.0457 (4)0.0143 (4)
I20.0525 (5)0.0813 (7)0.0586 (4)0.0069 (5)0.0116 (3)0.0170 (4)
Geometric parameters (Å, º) top
C1—C61.373 (14)C7—C81.387 (15)
C1—C21.408 (14)C7—C121.401 (14)
C1—I12.089 (10)C7—I22.082 (10)
C2—C31.379 (15)C8—C91.412 (14)
C2—Cl11.751 (11)C8—Cl31.740 (10)
C3—C41.354 (15)C9—C101.404 (14)
C3—H30.9300C9—H90.9300
C4—C51.440 (14)C10—C111.371 (15)
C4—Br11.869 (10)C10—Br21.889 (9)
C5—C61.406 (14)C11—C121.382 (15)
C5—H50.9300C11—H110.9300
C6—Cl21.745 (9)C12—Cl41.702 (12)
C6—C1—C2116.4 (9)C8—C7—C12116.9 (9)
C6—C1—I1121.2 (7)C8—C7—I2120.8 (7)
C2—C1—I1122.4 (8)C12—C7—I2122.1 (9)
C3—C2—C1124.1 (11)C7—C8—C9123.7 (9)
C3—C2—Cl1116.4 (8)C7—C8—Cl3121.0 (7)
C1—C2—Cl1119.5 (9)C9—C8—Cl3115.3 (8)
C4—C3—C2117.3 (9)C10—C9—C8115.9 (10)
C4—C3—H3121.3C10—C9—H9122.0
C2—C3—H3121.3C8—C9—H9122.0
C3—C4—C5123.0 (9)C11—C10—C9122.0 (9)
C3—C4—Br1119.0 (8)C11—C10—Br2120.2 (8)
C5—C4—Br1118.0 (8)C9—C10—Br2117.8 (9)
C6—C5—C4115.9 (10)C10—C11—C12120.0 (10)
C6—C5—H5122.0C10—C11—H11120.0
C4—C5—H5122.0C12—C11—H11120.0
C1—C6—C5123.2 (9)C11—C12—C7121.5 (11)
C1—C6—Cl2122.2 (8)C11—C12—Cl4118.5 (9)
C5—C6—Cl2114.6 (8)C7—C12—Cl4120.0 (9)
C6—C1—C2—C30.8 (15)C12—C7—C8—C90.7 (15)
I1—C1—C2—C3179.2 (8)I2—C7—C8—C9175.4 (8)
C6—C1—C2—Cl1179.8 (7)C12—C7—C8—Cl3179.2 (8)
I1—C1—C2—Cl10.3 (12)I2—C7—C8—Cl34.4 (12)
C1—C2—C3—C40.5 (16)C7—C8—C9—C100.3 (16)
Cl1—C2—C3—C4179.0 (8)Cl3—C8—C9—C10179.8 (8)
C2—C3—C4—C51.0 (15)C8—C9—C10—C110.0 (16)
C2—C3—C4—Br1176.7 (7)C8—C9—C10—Br2178.0 (7)
C3—C4—C5—C60.3 (15)C9—C10—C11—C121.2 (16)
Br1—C4—C5—C6177.4 (7)Br2—C10—C11—C12176.7 (8)
C2—C1—C6—C51.5 (14)C10—C11—C12—C72.3 (16)
I1—C1—C6—C5178.4 (8)C10—C11—C12—Cl4179.6 (8)
C2—C1—C6—Cl2179.5 (7)C8—C7—C12—C112.0 (15)
I1—C1—C6—Cl20.4 (12)I2—C7—C12—C11176.6 (7)
C4—C5—C6—C11.0 (15)C8—C7—C12—Cl4179.9 (8)
C4—C5—C6—Cl2179.2 (7)I2—C7—C12—Cl45.2 (12)
 

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