organic compounds
The molecule of the title compound, C8Cl3IN2, is disordered in the crystal. For the major component, there is an IN intermolecular contact of 3.06 (3) Å and two ClN contacts of 3.10 (3) and 3.19 (3) Å. In all three contacts, the angle is approximately linear at the halogen atom and bent at the nitrogen.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000133/om6205sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000133/om6205Isup2.hkl |
CCDC reference: 234860
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2,5,6-trichloro-4-iodoisophthalonitrile top
Crystal data top
C8Cl3IN2 | Dx = 2.247 Mg m−3 |
Mr = 357.35 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 900 reflections |
Hall symbol: P 4nw 2abw | θ = 3.2–29.5° |
a = 6.3657 (16) Å | µ = 3.75 mm−1 |
c = 52.125 (13) Å | T = 297 K |
V = 2112.2 (9) Å3 | Plate, colorless |
Z = 8 | 0.15 × 0.10 × 0.01 mm |
F(000) = 1328 |
Data collection top
Siemens SMART area-detector diffractometer | 1872 independent reflections |
Radiation source: fine-focus sealed tube | 1406 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
ω scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: analytical (XPREP in SHELXTL; Sheldrick, 1994) | h = −7→7 |
Tmin = 0.70, Tmax = 0.96 | k = −7→7 |
18634 measured reflections | l = −61→61 |
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)] = 0.050 | w = 1/[σ2(Fo2) + (0.0065P)2 + 9.13P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = 0.02 |
S = 1.16 | Δρmax = 0.43 e Å−3 |
1872 reflections | Δρmin = −0.48 e Å−3 |
171 parameters | Absolute structure: Flack (1983) |
34 restraints | Absolute structure parameter: −0.02 (8) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
I14 | 0.9309 (4) | 0.5301 (4) | 0.01496 (4) | 0.0555 (4) | 0.735 (3) |
Cl12 | 0.2249 (13) | 0.4964 (10) | 0.0825 (3) | 0.052 (2) | 0.735 (3) |
Cl15 | 1.032 (3) | 0.972 (3) | 0.0481 (5) | 0.0669 (14) | 0.735 (3) |
Cl16 | 0.751 (3) | 1.145 (3) | 0.0930 (4) | 0.0531 (19) | 0.735 (3) |
N11 | 0.303 (4) | 0.932 (6) | 0.1248 (5) | 0.070 (7) | 0.735 (3) |
C17 | 0.394 (3) | 0.883 (4) | 0.1078 (6) | 0.042 (4) | 0.735 (3) |
N13 | 0.434 (4) | 0.210 (4) | 0.0313 (8) | 0.066 (5) | 0.735 (3) |
C18 | 0.494 (3) | 0.365 (3) | 0.0405 (5) | 0.045 (4) | 0.735 (3) |
C11 | 0.511 (2) | 0.807 (2) | 0.0851 (4) | 0.036 (2) | 0.735 (3) |
C12 | 0.447 (2) | 0.630 (2) | 0.0726 (4) | 0.042 (3) | 0.735 (3) |
C13 | 0.563 (3) | 0.549 (3) | 0.0524 (4) | 0.043 (3) | 0.735 (3) |
C14 | 0.747 (3) | 0.657 (2) | 0.0450 (3) | 0.045 (3) | 0.735 (3) |
C15 | 0.808 (2) | 0.844 (2) | 0.0569 (4) | 0.041 (3) | 0.735 (3) |
C16 | 0.691 (3) | 0.915 (3) | 0.0780 (4) | 0.044 (3) | 0.735 (3) |
I24 | 0.783 (3) | 1.160 (2) | 0.0972 (3) | 0.0531 (19) | 0.265 (3) |
Cl22 | 0.247 (4) | 0.449 (4) | 0.0835 (8) | 0.052 (2) | 0.265 (3) |
Cl25 | 1.034 (9) | 0.945 (9) | 0.0468 (13) | 0.0669 (14) | 0.265 (3) |
Cl26 | 0.895 (5) | 0.530 (5) | 0.0191 (5) | 0.0555 (4) | 0.265 (3) |
N21 | 0.481 (13) | 0.174 (11) | 0.030 (2) | 0.066 (5) | 0.265 (3) |
C27 | 0.518 (8) | 0.326 (8) | 0.0391 (11) | 0.045 (4) | 0.265 (3) |
N23 | 0.267 (12) | 0.929 (16) | 0.1194 (18) | 0.070 (7) | 0.265 (3) |
C28 | 0.375 (10) | 0.856 (11) | 0.1038 (18) | 0.042 (4) | 0.265 (3) |
C21 | 0.576 (6) | 0.523 (6) | 0.0524 (9) | 0.043 (3) | 0.265 (3) |
C22 | 0.458 (5) | 0.595 (4) | 0.0723 (8) | 0.042 (3) | 0.265 (3) |
C23 | 0.511 (6) | 0.778 (6) | 0.0850 (9) | 0.036 (2) | 0.265 (3) |
C24 | 0.698 (6) | 0.881 (6) | 0.0777 (10) | 0.044 (3) | 0.265 (3) |
C25 | 0.822 (5) | 0.807 (5) | 0.0575 (7) | 0.041 (3) | 0.265 (3) |
C26 | 0.760 (5) | 0.622 (5) | 0.0450 (7) | 0.045 (3) | 0.265 (3) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
I14 | 0.0535 (11) | 0.0615 (6) | 0.0514 (10) | 0.0062 (7) | 0.0143 (6) | −0.0016 (6) |
Cl12 | 0.048 (2) | 0.047 (4) | 0.062 (2) | −0.010 (3) | 0.009 (2) | −0.005 (4) |
Cl15 | 0.0575 (17) | 0.059 (5) | 0.085 (3) | −0.012 (3) | 0.0140 (18) | 0.006 (3) |
Cl16 | 0.053 (4) | 0.057 (2) | 0.048 (5) | −0.014 (2) | −0.015 (3) | −0.008 (2) |
N11 | 0.076 (12) | 0.085 (8) | 0.049 (14) | 0.010 (8) | 0.008 (11) | −0.017 (9) |
C17 | 0.054 (8) | 0.037 (9) | 0.035 (12) | 0.001 (5) | 0.001 (8) | −0.010 (5) |
N13 | 0.034 (14) | 0.073 (11) | 0.091 (8) | 0.003 (9) | 0.000 (12) | −0.031 (9) |
C18 | 0.028 (7) | 0.053 (10) | 0.053 (7) | −0.010 (7) | 0.009 (5) | −0.001 (7) |
C11 | 0.035 (6) | 0.037 (7) | 0.038 (5) | −0.013 (5) | 0.005 (4) | 0.001 (5) |
C12 | 0.035 (6) | 0.040 (7) | 0.051 (6) | 0.006 (5) | −0.009 (5) | 0.005 (6) |
C13 | 0.050 (6) | 0.038 (7) | 0.042 (5) | 0.001 (6) | 0.000 (5) | −0.007 (5) |
C14 | 0.046 (6) | 0.043 (8) | 0.047 (6) | 0.004 (6) | 0.003 (5) | 0.016 (6) |
C15 | 0.040 (6) | 0.029 (7) | 0.053 (6) | 0.004 (5) | −0.002 (5) | 0.017 (6) |
C16 | 0.049 (7) | 0.039 (8) | 0.043 (5) | −0.001 (6) | −0.007 (5) | 0.009 (6) |
I24 | 0.053 (4) | 0.057 (2) | 0.048 (5) | −0.014 (2) | −0.015 (3) | −0.008 (2) |
Cl22 | 0.048 (2) | 0.047 (4) | 0.062 (2) | −0.010 (3) | 0.009 (2) | −0.005 (4) |
Cl25 | 0.0575 (17) | 0.059 (5) | 0.085 (3) | −0.012 (3) | 0.0140 (18) | 0.006 (3) |
Cl26 | 0.0535 (11) | 0.0615 (6) | 0.0514 (10) | 0.0062 (7) | 0.0143 (6) | −0.0016 (6) |
N21 | 0.034 (14) | 0.073 (11) | 0.091 (8) | 0.003 (9) | 0.000 (12) | −0.031 (9) |
C27 | 0.028 (7) | 0.053 (10) | 0.053 (7) | −0.010 (7) | 0.009 (5) | −0.001 (7) |
N23 | 0.076 (12) | 0.085 (8) | 0.049 (14) | 0.010 (8) | 0.008 (11) | −0.017 (9) |
C28 | 0.054 (8) | 0.037 (9) | 0.035 (12) | 0.001 (5) | 0.001 (8) | −0.010 (5) |
C21 | 0.050 (6) | 0.038 (7) | 0.042 (5) | 0.001 (6) | 0.000 (5) | −0.007 (5) |
C22 | 0.035 (6) | 0.040 (7) | 0.051 (6) | 0.006 (5) | −0.009 (5) | 0.005 (6) |
C23 | 0.035 (6) | 0.037 (7) | 0.038 (5) | −0.013 (5) | 0.005 (4) | 0.001 (5) |
C24 | 0.049 (7) | 0.039 (8) | 0.043 (5) | −0.001 (6) | −0.007 (5) | 0.009 (6) |
C25 | 0.040 (6) | 0.029 (7) | 0.053 (6) | 0.004 (5) | −0.002 (5) | 0.017 (6) |
C26 | 0.046 (6) | 0.043 (8) | 0.047 (6) | 0.004 (6) | 0.003 (5) | 0.016 (6) |
Geometric parameters (Å, º) top
I14—C14 | 2.113 (15) | I24—C24 | 2.113 (15) |
Cl12—C12 | 1.731 (10) | Cl22—C22 | 1.732 (10) |
Cl15—C15 | 1.708 (9) | Cl25—C25 | 1.708 (9) |
Cl16—C16 | 1.704 (19) | Cl26—C26 | 1.704 (19) |
N11—C17 | 1.104 (18) | N21—C27 | 1.104 (18) |
C17—C11 | 1.48 (2) | C27—C21 | 1.48 (2) |
N13—C18 | 1.160 (19) | N23—C28 | 1.160 (19) |
C18—C13 | 1.40 (2) | C28—C23 | 1.40 (2) |
C11—C12 | 1.361 (19) | C21—C22 | 1.361 (19) |
C11—C16 | 1.386 (19) | C21—C26 | 1.386 (19) |
C12—C13 | 1.38 (2) | C22—C23 | 1.38 (2) |
C13—C14 | 1.415 (19) | C23—C24 | 1.415 (19) |
C14—C15 | 1.40 (2) | C24—C25 | 1.40 (2) |
C15—C16 | 1.40 (2) | C25—C26 | 1.40 (2) |
N11—C17—C11 | 177 (2) | N21—C27—C21 | 176 (3) |
N13—C18—C13 | 178 (2) | N23—C28—C23 | 177 (4) |
C12—C11—C16 | 121.9 (13) | C22—C21—C26 | 121.9 (13) |
C12—C11—C17 | 120.2 (12) | C22—C21—C27 | 120.2 (12) |
C16—C11—C17 | 117.8 (12) | C26—C21—C27 | 117.8 (12) |
C11—C12—C13 | 120.9 (9) | C21—C22—C23 | 120.8 (9) |
C11—C12—Cl12 | 120.5 (12) | C21—C22—Cl22 | 120.5 (12) |
C13—C12—Cl12 | 118.5 (12) | C23—C22—Cl22 | 118.5 (12) |
C12—C13—C18 | 119.2 (12) | C22—C23—C28 | 119.2 (12) |
C12—C13—C14 | 118.0 (12) | C22—C23—C24 | 118.0 (12) |
C18—C13—C14 | 122.8 (13) | C28—C23—C24 | 122.8 (13) |
C15—C14—C13 | 121.3 (12) | C25—C24—C23 | 121.3 (12) |
C15—C14—I14 | 120.2 (11) | C25—C24—I24 | 120.2 (11) |
C13—C14—I14 | 118.5 (11) | C23—C24—I24 | 118.5 (11) |
C14—C15—C16 | 118.6 (9) | C24—C25—C26 | 118.7 (9) |
C14—C15—Cl15 | 121.3 (13) | C24—C25—Cl25 | 121.3 (13) |
C16—C15—Cl15 | 119.9 (13) | C26—C25—Cl25 | 119.9 (13) |
C11—C16—C15 | 119.2 (13) | C21—C26—C25 | 119.2 (13) |
C11—C16—Cl16 | 119.3 (13) | C21—C26—Cl26 | 119.3 (13) |
C15—C16—Cl16 | 121.2 (13) | C25—C26—Cl26 | 121.3 (13) |
Distances and angles (Å, °) in the I···N and Cl···N contacts in
ICl3C6(CN)2 and Cl4C6(CN)2a top
X | N | C—X···N | X···N | X···N—C |
I14 | N13i | 169 (1) | 3.06 (3) | 139 (3) |
I14 | N21i | 164 (2) | 2.83 (8) | 144 (8) |
Cl26 | N13i | 169 (1) | 3.36 (3) | 140 (2) |
Cl26 | N21i | 165 (2) | 3.13 (8) | 146 (8) |
Cl14 | N13 | 134 | 3.39 | 165 |
Cl15 | N13ii | 179 (2) | 3.10 (3) | 125 (2) |
Cl15 | N21ii | 174 (1) | 3.27 (10) | 115 (7) |
Cl25 | N13ii | 176 (3) | 3.16 (4) | 128 (2) |
Cl25 | N21ii | 173 (5) | 3.31 (10) | 117 (7) |
Cl15 | N13 | 177 | 3.07 | 122 |
Cl16 | N11iii | 172 (1) | 3.19 (3) | 135 (2) |
Cl16 | N23iii | 166 (2) | 3.34 (7) | 139 (5) |
I24 | N11iii | 168 (1) | 2.99 (3) | 131 (2) |
I24 | N23iii | 163 (2) | 3.14 (7) | 135 (5) |
Cl16 | N13 | 167 | 314 | 137 |
Notes: (a) the entries in each set of contacts comprise the interaction between the major components, then that between the major and minor components, then the minor–major, then the minor–minor, and finally the corresponding values in the Cl4C6(CN)2 structure. The latter are given without error estimates. Symmetry codes: (i) 1+y, x, -z; (ii) 1+x, 1+y, z; (iii) 1/2+x, 5/2-y, 1/4-z. |