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The components of the title compound, C8H6Br6 and C8H4Br6, are hexa- and tetra­bromo­penta­lene derivatives, which were obtained by the treatment of hexa­hydro­penta­lene with a tenfold excess of bromine. The asymmetric unit consists of two half-mol­ecules. Crystallographic centres of symmetry are located at the mid-points of the central C=C and C-C bonds. The repulsive inter­actions between the Br atoms may affect the mol­ecular geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012645/er2002sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012645/er2002Isup2.hkl
Contains datablock I

CCDC reference: 610759

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.018 Å
  • R factor = 0.123
  • wR factor = 0.299
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 5.381 Test value = 3.500 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 5.38 e/A   3 PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 18
Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -2.976 Test value = -2.625 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.123 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.299 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT082_ALERT_2_C High R1 Value .................................. 0.12 PLAT084_ALERT_2_C High R2 Value .................................. 0.30 PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -2.98 e/A   3 PLAT213_ALERT_2_C Atom C2 has ADP max/min Ratio ............. 3.20 oblate PLAT213_ALERT_2_C Atom C5 has ADP max/min Ratio ............. 3.20 oblate PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.74 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br5 .. 3.57 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br3 .. Br5 .. 3.60 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br6 .. Br6 .. 3.48 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1R,3S,4S,6R)-1,2,3,4,5,6-hexabromo-1,2,3,4,5,6-hexahydropentalene– (1R,2R,4S,5S)-1,2,3,4,5,6-hexabromo-1,2,4,5-tetrahydropentalene (1/1) top
Crystal data top
C8H6Br6·C8H4Br6Z = 1
Mr = 1161.04F(000) = 526
Triclinic, P1Dx = 2.927 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 8.258 (2) ÅCell parameters from 25 reflections
b = 8.483 (2) Åθ = 5.2–22.3°
c = 10.850 (5) ŵ = 21.72 mm1
α = 72.274 (3)°T = 298 K
β = 71.128 (3)°Block, colourless
γ = 69.733 (2)°0.15 × 0.10 × 0.10 mm
V = 658.6 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2314 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 69.0°, θmin = 4.4°
non–profiled ω scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 910
Tmin = 0.109, Tmax = 0.113l = 1213
2495 measured reflections3 standard reflections every 120 min
2364 independent reflections intensity decay: 1%
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)] = 0.123H-atom parameters constrained
wR(F2) = 0.299 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.36(Δ/σ)max < 0.001
2364 reflectionsΔρmax = 5.38 e Å3
128 parametersΔρmin = 2.98 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0054 (10)
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
Br10.08028 (16)0.08214 (18)0.11215 (12)0.0379 (5)
Br20.4616 (2)0.2754 (2)0.16111 (15)0.0537 (6)
Br30.4460 (2)0.2939 (2)0.26335 (13)0.0485 (5)
Br40.0058 (2)0.56505 (18)0.16837 (12)0.0406 (5)
Br50.1708 (2)0.2219 (2)0.41499 (13)0.0447 (5)
Br60.3112 (2)0.1602 (2)0.55240 (18)0.0537 (6)
C10.4338 (14)0.0632 (14)0.0256 (10)0.027 (2)
C20.2924 (15)0.0019 (17)0.0278 (10)0.033 (2)
C30.3676 (16)0.1941 (17)0.0071 (11)0.033 (2)
C40.5232 (16)0.2324 (15)0.0649 (11)0.031 (2)
C50.0059 (15)0.5573 (15)0.4382 (9)0.028 (2)
C60.0194 (17)0.4688 (17)0.3460 (12)0.035 (3)
C70.0440 (16)0.2849 (17)0.4054 (11)0.034 (2)
C80.0565 (16)0.2639 (15)0.5466 (11)0.032 (2)
H20.26640.04110.11590.040*
H30.27700.24950.06930.040*
H40.62440.32270.02930.038*
H70.15190.21520.35490.040*
H80.02120.19700.61350.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0324 (7)0.0524 (9)0.0236 (7)0.0082 (5)0.0024 (5)0.0147 (6)
Br20.0663 (10)0.0639 (10)0.0350 (9)0.0022 (8)0.0158 (7)0.0308 (7)
Br30.0662 (10)0.0615 (10)0.0170 (8)0.0278 (8)0.0084 (6)0.0025 (6)
Br40.0564 (9)0.0489 (9)0.0135 (7)0.0162 (6)0.0080 (5)0.0013 (5)
Br50.0512 (9)0.0618 (10)0.0277 (8)0.0264 (7)0.0043 (6)0.0119 (6)
Br60.0499 (9)0.0498 (9)0.0607 (11)0.0065 (7)0.0287 (8)0.0178 (7)
C10.032 (5)0.027 (5)0.017 (5)0.008 (4)0.003 (4)0.002 (4)
C20.031 (5)0.053 (7)0.007 (4)0.006 (5)0.001 (4)0.008 (4)
C30.034 (6)0.050 (7)0.020 (5)0.017 (5)0.005 (4)0.007 (5)
C40.039 (6)0.037 (6)0.015 (5)0.014 (5)0.002 (4)0.001 (4)
C50.035 (5)0.041 (6)0.006 (5)0.007 (4)0.004 (4)0.007 (4)
C60.038 (6)0.043 (6)0.020 (6)0.013 (5)0.003 (4)0.006 (5)
C70.036 (6)0.046 (7)0.016 (5)0.012 (5)0.001 (4)0.009 (5)
C80.038 (6)0.032 (6)0.023 (6)0.006 (5)0.007 (5)0.006 (4)
Geometric parameters (Å, º) top
Br1—C21.980 (11)C3—C41.502 (16)
Br2—C31.972 (12)C4—C1i1.500 (15)
Br3—C41.994 (11)C4—H40.9800
Br4—C61.874 (12)C5—C5ii1.41 (2)
Br5—C71.987 (12)C5—C8ii1.474 (16)
Br6—C81.993 (12)C6—C51.349 (16)
C1—C1i1.37 (2)C6—C71.464 (18)
C1—C21.443 (16)C7—H70.9800
C1—C4i1.500 (15)C8—C5ii1.474 (16)
C2—H20.9800C8—C71.520 (15)
C3—C21.532 (18)C8—H80.9800
C3—H30.9800
C1i—C1—C2113.7 (13)Br3—C4—H4111.8
C1i—C1—C4i109.4 (12)C6—C5—C5ii109.6 (14)
C2—C1—C4i136.9 (10)C6—C5—C8ii140.2 (10)
C1—C2—C3102.9 (10)C5ii—C5—C8ii109.9 (11)
C1—C2—Br1108.2 (8)C5—C6—C7111.1 (11)
C3—C2—Br1111.0 (8)C5—C6—Br4125.7 (10)
C1—C2—H2111.5C7—C6—Br4123.0 (9)
C3—C2—H2111.5C6—C7—C8105.0 (10)
Br1—C2—H2111.5C6—C7—Br5108.9 (9)
C4—C3—C2107.6 (10)C8—C7—Br5108.7 (8)
C4—C3—Br2107.1 (8)C6—C7—H7111.3
C2—C3—Br2107.6 (7)C8—C7—H7111.3
C4—C3—H3111.5Br5—C7—H7111.3
C2—C3—H3111.5C5ii—C8—C7103.3 (9)
Br2—C3—H3111.5C5ii—C8—Br6107.4 (8)
C1i—C4—C3103.7 (9)C7—C8—Br6108.0 (8)
C1i—C4—Br3108.1 (7)C5ii—C8—H8112.5
C3—C4—Br3109.4 (8)C7—C8—H8112.5
C1i—C4—H4111.8Br6—C8—H8112.5
C3—C4—H4111.8
C1i—C1—C2—C310.0 (15)C7—C6—C5—C5ii2.1 (17)
C4i—C1—C2—C3170.2 (12)Br4—C6—C5—C5ii177.0 (11)
C1i—C1—C2—Br1107.6 (13)C7—C6—C5—C8ii171.1 (14)
C4i—C1—C2—Br172.2 (14)Br4—C6—C5—C8ii4 (2)
C4—C3—C2—C115.9 (11)C5—C6—C7—C87.6 (14)
Br2—C3—C2—C199.1 (8)Br4—C6—C7—C8177.3 (8)
C4—C3—C2—Br199.6 (9)C5—C6—C7—Br5108.6 (10)
Br2—C3—C2—Br1145.3 (5)Br4—C6—C7—Br566.4 (11)
C2—C3—C4—C1i15.9 (12)C5ii—C8—C7—C69.7 (13)
Br2—C3—C4—C1i99.6 (9)Br6—C8—C7—C6104.0 (9)
C2—C3—C4—Br399.2 (9)C5ii—C8—C7—Br5106.8 (9)
Br2—C3—C4—Br3145.4 (6)Br6—C8—C7—Br5139.6 (6)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z+1.
 

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