organic compounds
2,6-Dibromo-4-chlorobenzonitrile, C7H2Br2ClN, forms layers in the crystal structure, with BrN contacts of 3.049 (2) Å the strongest intermolecular interactions. The crystal structure is isomorphous with 2,4,6-tribromobenzonitrile.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014686/ac6176sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014686/ac6176Isup2.hkl |
CCDC reference: 274321
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
C7H2Br2ClN | F(000) = 276 |
Mr = 295.37 | Dx = 2.346 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 2165 reflections |
a = 8.666 (2) Å | θ = 2.4–27.4° |
b = 10.125 (3) Å | µ = 9.94 mm−1 |
c = 4.7776 (12) Å | T = 173 K |
β = 93.98 (1)° | Needle, colorless |
V = 418.19 (19) Å3 | 0.45 × 0.15 × 0.10 mm |
Z = 2 |
Data collection top
Siemens area-detector diffractometer | 1001 independent reflections |
Radiation source: fine-focus sealed tube | 930 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −11→5 |
Tmin = 0.19, Tmax = 0.37 | k = −13→13 |
2839 measured reflections | l = −6→6 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | All 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 reflections | Δρmax = 0.43 e Å−3 |
63 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.047 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br2 | 0.19034 (3) | 0.53047 (2) | 0.33819 (5) | 0.02675 (13) | |
Cl4 | 0.57102 (9) | 0.2500 | 1.09654 (16) | 0.0267 (2) | |
N1 | −0.0135 (4) | 0.2500 | −0.0187 (7) | 0.0326 (7) | |
C1 | 0.2005 (3) | 0.2500 | 0.3857 (6) | 0.0216 (6) | |
C2 | 0.2606 (3) | 0.3689 (2) | 0.4963 (5) | 0.0215 (4) | |
C3 | 0.3745 (3) | 0.3697 (3) | 0.7146 (5) | 0.0228 (5) | |
C4 | 0.4286 (4) | 0.2500 | 0.8216 (6) | 0.0222 (6) | |
C5 | 0.0815 (4) | 0.2500 | 0.1607 (7) | 0.0248 (7) | |
H3 | 0.413 (4) | 0.452 (3) | 0.772 (6) | 0.026 (7)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br2 | 0.02831 (18) | 0.01858 (17) | 0.03282 (18) | 0.00133 (8) | −0.00176 (10) | 0.00351 (8) |
Cl4 | 0.0270 (4) | 0.0293 (4) | 0.0230 (4) | 0.000 | −0.0047 (3) | 0.000 |
N1 | 0.0320 (16) | 0.0247 (15) | 0.0393 (18) | 0.000 | −0.0096 (13) | 0.000 |
C1 | 0.0198 (15) | 0.0237 (17) | 0.0212 (14) | 0.000 | 0.0013 (11) | 0.000 |
C2 | 0.0231 (10) | 0.0179 (11) | 0.0237 (10) | 0.0017 (9) | 0.0032 (8) | 0.0019 (8) |
C3 | 0.0230 (11) | 0.0211 (12) | 0.0243 (11) | −0.0014 (9) | 0.0015 (8) | −0.0021 (8) |
C4 | 0.0225 (15) | 0.0245 (17) | 0.0193 (14) | 0.000 | 0.0003 (11) | 0.000 |
C5 | 0.0257 (16) | 0.0189 (16) | 0.0293 (16) | 0.000 | −0.0012 (13) | 0.000 |
Geometric parameters (Å, º) top
Br2—C2 | 1.885 (2) | C1—C5 | 1.437 (4) |
Cl4—C4 | 1.739 (3) | C2—C3 | 1.385 (3) |
N1—C5 | 1.146 (5) | C3—C4 | 1.385 (3) |
C1—C2 | 1.400 (3) | C3—H3 | 0.93 (3) |
C1—C2i | 1.400 (3) | C4—C3i | 1.385 (3) |
C2—C1—C2i | 118.5 (3) | C4—C3—H3 | 124.9 (18) |
C2—C1—C5 | 120.73 (14) | C2—C3—H3 | 116.5 (18) |
C2i—C1—C5 | 120.73 (14) | C3i—C4—C3 | 122.2 (3) |
C3—C2—C1 | 121.1 (2) | C3i—C4—Cl4 | 118.91 (15) |
C3—C2—Br2 | 119.32 (18) | C3—C4—Cl4 | 118.91 (15) |
C1—C2—Br2 | 119.57 (17) | N1—C5—C1 | 180.0 (4) |
C4—C3—C2 | 118.6 (2) |
Symmetry code: (i) x, −y+1/2, z. |