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In the crystal structure of the title compound, C6H4Br2ClN, all atoms but Br are located on a crystallographic mirror plane. The crystal packing is stabilized by offset π–π stacking.
Supporting information
CCDC reference: 298426
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.022
- wR factor = 0.054
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. N1 .. 3.19 Ang.
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
2 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,
1997); software used to prepare material for publication: SHELXTL (Bruker, 1999).
6-Chloro-2-(dibromomethyl)pyridine
top
Crystal data top
C6H4Br2ClN | F(000) = 536 |
Mr = 285.37 | Dx = 2.276 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 2146 reflections |
a = 14.839 (3) Å | θ = 2.8–27.7° |
b = 7.0388 (12) Å | µ = 9.97 mm−1 |
c = 7.9745 (14) Å | T = 293 K |
V = 832.9 (3) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.22 × 0.18 mm |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 803 independent reflections |
Radiation source: fine-focus sealed tube | 725 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 25.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −15→17 |
Tmin = 0.06, Tmax = 0.16 | k = −8→8 |
4261 measured reflections | l = −9→8 |
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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.055 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0267P)2 + 0.4103P] where P = (Fo2 + 2Fc2)/3 |
803 reflections | (Δ/σ)max < 0.001 |
58 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.206716 (16) | 0.02502 (4) | 0.38211 (4) | 0.04445 (14) | |
Cl1 | 0.53522 (7) | 0.2500 | 0.83011 (16) | 0.0724 (4) | |
N1 | 0.39728 (18) | 0.2500 | 0.6301 (3) | 0.0316 (6) | |
C1 | 0.2573 (2) | 0.2500 | 0.4863 (4) | 0.0293 (7) | |
H1 | 0.2394 | 0.2500 | 0.6046 | 0.035* | |
C2 | 0.3583 (2) | 0.2500 | 0.4793 (4) | 0.0293 (7) | |
C3 | 0.4869 (2) | 0.2500 | 0.6317 (5) | 0.0398 (9) | |
C4 | 0.5409 (2) | 0.2500 | 0.4931 (5) | 0.0468 (10) | |
H4 | 0.6034 | 0.2500 | 0.5022 | 0.056* | |
C5 | 0.4990 (3) | 0.2500 | 0.3399 (5) | 0.0506 (10) | |
H5 | 0.5331 | 0.2500 | 0.2421 | 0.061* | |
C6 | 0.4062 (2) | 0.2500 | 0.3314 (5) | 0.0443 (9) | |
H6 | 0.3768 | 0.2500 | 0.2285 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0379 (2) | 0.0393 (2) | 0.0562 (2) | −0.00643 (10) | −0.00110 (11) | −0.01258 (12) |
Cl1 | 0.0461 (6) | 0.1081 (11) | 0.0631 (7) | 0.000 | −0.0287 (5) | 0.000 |
N1 | 0.0268 (15) | 0.0305 (15) | 0.0377 (16) | 0.000 | −0.0024 (12) | 0.000 |
C1 | 0.0280 (17) | 0.0309 (18) | 0.0291 (17) | 0.000 | −0.0027 (13) | 0.000 |
C2 | 0.0275 (17) | 0.0252 (17) | 0.0353 (19) | 0.000 | −0.0016 (13) | 0.000 |
C3 | 0.0309 (19) | 0.037 (2) | 0.052 (2) | 0.000 | −0.0108 (16) | 0.000 |
C4 | 0.0244 (18) | 0.044 (2) | 0.072 (3) | 0.000 | 0.0030 (18) | 0.000 |
C5 | 0.037 (2) | 0.058 (3) | 0.056 (3) | 0.000 | 0.0170 (19) | 0.000 |
C6 | 0.040 (2) | 0.055 (2) | 0.038 (2) | 0.000 | 0.0055 (16) | 0.000 |
Geometric parameters (Å, º) top
Br1—C1 | 1.9397 (18) | C3—C4 | 1.366 (5) |
Cl1—C3 | 1.737 (4) | C4—C5 | 1.371 (6) |
N1—C3 | 1.329 (4) | C4—H4 | 0.9300 |
N1—C2 | 1.334 (4) | C5—C6 | 1.378 (5) |
C1—C2 | 1.499 (4) | C5—H5 | 0.9300 |
C1—H1 | 0.9800 | C6—H6 | 0.9300 |
C2—C6 | 1.378 (5) | | |
| | | |
C3—N1—C2 | 116.2 (3) | C4—C3—Cl1 | 119.6 (3) |
C2—C1—Br1 | 111.78 (13) | C3—C4—C5 | 117.1 (3) |
Br1—C1—Br1i | 109.45 (15) | C3—C4—H4 | 121.5 |
C2—C1—H1 | 107.9 | C5—C4—H4 | 121.5 |
Br1—C1—H1 | 107.9 | C4—C5—C6 | 119.8 (4) |
N1—C2—C6 | 123.2 (3) | C4—C5—H5 | 120.1 |
N1—C2—C1 | 113.6 (3) | C6—C5—H5 | 120.1 |
C6—C2—C1 | 123.2 (3) | C2—C6—C5 | 118.2 (4) |
N1—C3—C4 | 125.4 (3) | C2—C6—H6 | 120.9 |
N1—C3—Cl1 | 114.9 (3) | C5—C6—H6 | 120.9 |
Symmetry code: (i) x, −y+1/2, z. |
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