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Crystals of the title compound, C6H4BrI, were obtained by growth on a two-dimensional self-assembled monolayer template. Single-crystal X-ray diffraction at 110 K revealed a centrosymmetric structure in which the center of the benzene ring lies on an inversion center and the halogen atoms are statistically disordered. The monoclinic structure reported here is isostructural with p-dibromobenzene but not with p-diiodobenzene.
Supporting information
CCDC reference: 289723
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.023
- wR factor = 0.059
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT301_ALERT_3_C Main Residue Disorder ......................... 20.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C2 ... 1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C3_a ... 1.39 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.20 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C6H4BrI | F(000) = 256 |
Mr = 282.90 | Dx = 2.663 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2165 reflections |
a = 4.1120 (6) Å | θ = 2.8–32.6° |
b = 5.7936 (8) Å | µ = 10.09 mm−1 |
c = 14.931 (2) Å | T = 110 K |
β = 97.301 (11)° | Plate, colorless |
V = 352.83 (9) Å3 | 0.20 × 0.10 × 0.02 mm |
Z = 2 | |
Data collection top
Oxford Xcalibur3 diffractometer | 882 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 15.9890 pixels mm-1 | θmax = 28.3°, θmin = 4.5° |
ω scans | h = −5→3 |
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2005; Clark & Reid, 1995) | k = −7→7 |
Tmin = 0.182, Tmax = 0.652 | l = −18→19 |
2583 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0342P)2 + 0.3465P] where P = (Fo2 + 2Fc2)/3 |
882 reflections | (Δ/σ)max = 0.002 |
46 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
Special details top
Experimental. One reference frame collected every 50 frames. |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.1417 (9) | 0.3363 (6) | 0.3297 (2) | 0.0208 (9) | 0.50 |
Br1 | 0.1468 (14) | 0.3334 (8) | 0.3316 (4) | 0.0221 (15) | 0.50 |
C1 | 0.3551 (8) | 0.1365 (5) | 0.4306 (3) | 0.0225 (7) | |
C2 | 0.5026 (9) | −0.0694 (6) | 0.4109 (3) | 0.0253 (7) | |
H2A | 0.5016 | −0.1164 | 0.3499 | 0.030* | |
C3 | 0.6517 (8) | −0.2062 (6) | 0.4806 (3) | 0.0243 (7) | |
H3A | 0.7572 | −0.3461 | 0.4677 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0222 (14) | 0.0252 (15) | 0.0152 (12) | 0.0034 (9) | 0.0028 (8) | 0.0026 (8) |
Br1 | 0.021 (2) | 0.017 (2) | 0.027 (2) | −0.0040 (13) | −0.0031 (13) | 0.0019 (13) |
C1 | 0.0220 (15) | 0.0196 (14) | 0.0272 (18) | −0.0050 (12) | 0.0082 (13) | −0.0013 (12) |
C2 | 0.0305 (17) | 0.0228 (15) | 0.0242 (17) | −0.0048 (13) | 0.0096 (14) | −0.0079 (13) |
C3 | 0.0240 (16) | 0.0223 (14) | 0.0287 (19) | −0.0006 (12) | 0.0112 (14) | −0.0060 (13) |
Geometric parameters (Å, º) top
I1—C1 | 2.012 (6) | C2—C3 | 1.388 (5) |
Br1—C1 | 1.975 (7) | C2—H2A | 0.9500 |
C1—C2 | 1.387 (5) | C3—C1i | 1.390 (5) |
C1—C3i | 1.390 (5) | C3—H3A | 0.9500 |
| | | |
C2—C1—C3i | 121.0 (3) | C1—C2—H2A | 120.2 |
C2—C1—Br1 | 119.8 (3) | C3—C2—H2A | 120.2 |
C3i—C1—Br1 | 119.1 (3) | C2—C3—C1i | 119.3 (3) |
C2—C1—I1 | 119.7 (3) | C2—C3—H3A | 120.4 |
C3i—C1—I1 | 119.2 (3) | C1i—C3—H3A | 120.4 |
C1—C2—C3 | 119.7 (3) | | |
| | | |
C3i—C1—C2—C3 | −1.3 (5) | I1—C1—C2—C3 | 179.6 (3) |
Br1—C1—C2—C3 | 179.3 (3) | C1—C2—C3—C1i | 1.2 (5) |
Symmetry code: (i) −x+1, −y, −z+1. |
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