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2,6-Di­bromo-4-chloro­benzo­nitrile, C7H2Br2ClN, forms layers in the crystal structure, with Br...N contacts of 3.049 (2) Å the strongest intermolecular interactions. The crystal structure is isomorphous with 2,4,6-tri­bromo­benzo­nitrile.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014686/ac6176sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014686/ac6176Isup2.hkl
Contains datablock I

CCDC reference: 274321

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.022
  • wR factor = 0.057
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br2 .. N1 .. 3.05 Ang.
Alert level C PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C5 ... 1.44 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio
0 ALERT level A = In general: serious problem 1 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,6-Dibromo-4-chlorobenzonitrile top
Crystal data top
C7H2Br2ClNF(000) = 276
Mr = 295.37Dx = 2.346 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 2165 reflections
a = 8.666 (2) Åθ = 2.4–27.4°
b = 10.125 (3) ŵ = 9.94 mm1
c = 4.7776 (12) ÅT = 173 K
β = 93.98 (1)°Needle, colorless
V = 418.19 (19) Å30.45 × 0.15 × 0.10 mm
Z = 2
Data collection top
Siemens area-detector
diffractometer
1001 independent reflections
Radiation source: fine-focus sealed tube930 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 115
Tmin = 0.19, Tmax = 0.37k = 1313
2839 measured reflectionsl = 66
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)] = 0.022All H-atom parameters refined
wR(F2) = 0.057 w = 1/[σ2(Fo2) + (0.033P)2 + 0.25P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
1001 reflectionsΔρmax = 0.43 e Å3
63 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.047 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br20.19034 (3)0.53047 (2)0.33819 (5)0.02675 (13)
Cl40.57102 (9)0.25001.09654 (16)0.0267 (2)
N10.0135 (4)0.25000.0187 (7)0.0326 (7)
C10.2005 (3)0.25000.3857 (6)0.0216 (6)
C20.2606 (3)0.3689 (2)0.4963 (5)0.0215 (4)
C30.3745 (3)0.3697 (3)0.7146 (5)0.0228 (5)
C40.4286 (4)0.25000.8216 (6)0.0222 (6)
C50.0815 (4)0.25000.1607 (7)0.0248 (7)
H30.413 (4)0.452 (3)0.772 (6)0.026 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br20.02831 (18)0.01858 (17)0.03282 (18)0.00133 (8)0.00176 (10)0.00351 (8)
Cl40.0270 (4)0.0293 (4)0.0230 (4)0.0000.0047 (3)0.000
N10.0320 (16)0.0247 (15)0.0393 (18)0.0000.0096 (13)0.000
C10.0198 (15)0.0237 (17)0.0212 (14)0.0000.0013 (11)0.000
C20.0231 (10)0.0179 (11)0.0237 (10)0.0017 (9)0.0032 (8)0.0019 (8)
C30.0230 (11)0.0211 (12)0.0243 (11)0.0014 (9)0.0015 (8)0.0021 (8)
C40.0225 (15)0.0245 (17)0.0193 (14)0.0000.0003 (11)0.000
C50.0257 (16)0.0189 (16)0.0293 (16)0.0000.0012 (13)0.000
Geometric parameters (Å, º) top
Br2—C21.885 (2)C1—C51.437 (4)
Cl4—C41.739 (3)C2—C31.385 (3)
N1—C51.146 (5)C3—C41.385 (3)
C1—C21.400 (3)C3—H30.93 (3)
C1—C2i1.400 (3)C4—C3i1.385 (3)
C2—C1—C2i118.5 (3)C4—C3—H3124.9 (18)
C2—C1—C5120.73 (14)C2—C3—H3116.5 (18)
C2i—C1—C5120.73 (14)C3i—C4—C3122.2 (3)
C3—C2—C1121.1 (2)C3i—C4—Cl4118.91 (15)
C3—C2—Br2119.32 (18)C3—C4—Cl4118.91 (15)
C1—C2—Br2119.57 (17)N1—C5—C1180.0 (4)
C4—C3—C2118.6 (2)
Symmetry code: (i) x, y+1/2, z.
 

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