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The mol­ecule of the title compound, C20H16Br2, displays crystallographic inversion symmetry. Two C—H...Br inter­actions link the mol­ecules into layers parallel to (\overline{1}11). The shortest Br...Br contact is 4.1599 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025614/bt6714sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025614/bt6714Isup2.hkl
Contains datablock I

CCDC reference: 283759

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.057
  • Data-to-parameter ratio = 23.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. BR .. 3.13 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. BR .. 3.16 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

2,2''-bis(bromomethyl)-p-terphenyl top
Crystal data top
C20H16Br2Z = 1
Mr = 416.15F(000) = 206
Triclinic, P1Dx = 1.715 Mg m3
a = 4.4286 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4756 (6) ÅCell parameters from 4465 reflections
c = 12.4664 (12) Åθ = 2.7–30.4°
α = 96.032 (4)°µ = 5.02 mm1
β = 98.347 (4)°T = 133 K
γ = 96.155 (4)°Rectangular prism, colourless
V = 402.93 (6) Å30.25 × 0.10 × 0.07 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
2348 independent reflections
Radiation source: fine-focus sealed tube2056 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 8.192 pixels mm-1θmax = 30.0°, θmin = 1.7°
ω and φ scansh = 66
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 1010
Tmin = 0.488, Tmax = 0.704l = 1717
8315 measured reflections
Refinement top
Refinement on F2Primary atom site location: Patterson
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: riding
wR(F2) = 0.057H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.032P)2]
where P = (Fo2 + 2Fc2)/3
2348 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.33 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.4213 (0.0021) x + 4.6406 (0.0041) y + 4.6478 (0.0082) z = 2.9298 (0.0045)

* -0.0067 (0.0012) C4 * 0.0024 (0.0012) C5 * 0.0034 (0.0013) C6 * -0.0049 (0.0013) C7 * 0.0004 (0.0014) C8 * 0.0054 (0.0013) C9

Rms deviation of fitted atoms = 0.0044

4.2200 (0.0015) x - 0.0032 (0.0081) y + 1.6154 (0.0130) z = 2.9161 (0.0067)

Angle to previous plane (with approximate e.s.d.) = 54.13 (0.06)

* -0.0013 (0.0011) C1 * 0.0013 (0.0011) C2 * -0.0013 (0.0010) C3 * 0.0013 (0.0011) C1_$3 * -0.0013 (0.0011) C2_$3 * 0.0013 (0.0010) C3_$3

Rms deviation of fitted atoms = 0.0013

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
Br0.25108 (4)0.34454 (2)0.100201 (14)0.02420 (7)
C10.5066 (4)0.3147 (2)0.48155 (14)0.0205 (3)
H10.51080.18760.46820.025*
C20.5393 (4)0.4203 (2)0.39786 (13)0.0210 (4)
H20.56670.36480.32840.025*
C30.5324 (4)0.6086 (2)0.41475 (13)0.0185 (3)
C40.5764 (4)0.7268 (2)0.32756 (13)0.0179 (3)
C50.3932 (4)0.6977 (2)0.22374 (13)0.0173 (3)
C60.4493 (4)0.8159 (2)0.14722 (14)0.0208 (3)
H60.32560.79640.07710.025*
C70.6806 (4)0.9607 (2)0.17112 (15)0.0240 (4)
H70.71651.03870.11760.029*
C80.8594 (5)0.9909 (2)0.27374 (16)0.0252 (4)
H81.01791.09030.29120.030*
C90.8057 (4)0.8749 (2)0.35103 (14)0.0225 (4)
H90.92780.89710.42140.027*
C100.1314 (4)0.5490 (2)0.19254 (14)0.0196 (3)
H10A0.04640.59610.15210.024*
H10B0.06850.50570.25930.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.02757 (12)0.02080 (10)0.02267 (10)0.00043 (7)0.00274 (7)0.00022 (6)
C10.0259 (10)0.0172 (8)0.0187 (8)0.0053 (7)0.0032 (6)0.0016 (6)
C20.0265 (10)0.0219 (8)0.0150 (8)0.0065 (7)0.0036 (6)0.0006 (6)
C30.0190 (9)0.0206 (8)0.0163 (7)0.0040 (6)0.0020 (6)0.0037 (6)
C40.0201 (9)0.0175 (8)0.0176 (7)0.0057 (6)0.0044 (6)0.0030 (6)
C50.0178 (9)0.0176 (8)0.0176 (8)0.0054 (6)0.0046 (6)0.0022 (6)
C60.0230 (10)0.0221 (8)0.0183 (8)0.0054 (7)0.0026 (6)0.0052 (6)
C70.0280 (11)0.0197 (8)0.0276 (9)0.0051 (7)0.0092 (7)0.0086 (7)
C80.0258 (11)0.0187 (8)0.0298 (9)0.0013 (7)0.0040 (7)0.0013 (7)
C90.0246 (10)0.0214 (9)0.0200 (8)0.0027 (7)0.0010 (7)0.0004 (7)
C100.0191 (9)0.0213 (8)0.0186 (8)0.0028 (6)0.0030 (6)0.0025 (6)
Geometric parameters (Å, º) top
Br—C101.9806 (17)C7—C81.386 (3)
C1—C21.388 (2)C8—C91.391 (3)
C1—C3i1.400 (2)C1—H10.9500
C2—C31.405 (2)C2—H20.9500
C3—C41.492 (2)C6—H60.9500
C4—C91.395 (2)C7—H70.9500
C4—C51.407 (2)C8—H80.9500
C5—C61.397 (2)C9—H90.9500
C5—C101.494 (2)C10—H10A0.9900
C6—C71.384 (3)C10—H10B0.9900
C2—C1—C3i121.42 (16)C3i—C1—H1119.3
C1—C2—C3120.71 (15)C1—C2—H2119.6
C1i—C3—C2117.87 (15)C3—C2—H2119.6
C1i—C3—C4120.05 (15)C7—C6—H6119.2
C2—C3—C4122.04 (15)C5—C6—H6119.2
C9—C4—C5118.65 (15)C6—C7—H7120.3
C9—C4—C3118.39 (15)C8—C7—H7120.3
C5—C4—C3122.95 (16)C7—C8—H8120.2
C6—C5—C4119.13 (16)C9—C8—H8120.2
C6—C5—C10118.04 (15)C8—C9—H9119.2
C4—C5—C10122.79 (15)C4—C9—H9119.2
C7—C6—C5121.58 (16)C5—C10—H10A109.5
C6—C7—C8119.43 (16)Br—C10—H10A109.5
C7—C8—C9119.70 (17)C5—C10—H10B109.5
C8—C9—C4121.50 (17)Br—C10—H10B109.5
C5—C10—Br110.67 (12)H10A—C10—H10B108.1
C2—C1—H1119.3
C3i—C1—C2—C30.4 (3)C3—C4—C5—C102.0 (3)
C1—C2—C3—C1i0.4 (3)C4—C5—C6—C70.0 (3)
C1—C2—C3—C4178.10 (17)C10—C5—C6—C7177.77 (16)
C1i—C3—C4—C952.3 (2)C5—C6—C7—C80.7 (3)
C2—C3—C4—C9125.40 (19)C6—C7—C8—C90.4 (3)
C1i—C3—C4—C5126.36 (19)C7—C8—C9—C40.6 (3)
C2—C3—C4—C555.9 (3)C5—C4—C9—C81.2 (3)
C9—C4—C5—C60.9 (2)C3—C4—C9—C8179.95 (16)
C3—C4—C5—C6179.58 (16)C6—C5—C10—Br79.98 (17)
C9—C4—C5—C10176.70 (16)C4—C5—C10—Br102.37 (16)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Brii0.953.134.0272 (18)158
C7—H7···Briii0.953.163.8764 (18)134
Symmetry codes: (ii) x, y+1, z; (iii) x+1, y+1, z.
 

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