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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
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (Please check) = 0.000 Å
- R factor = 0.050
- wR factor = 0.095
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 50.00 Perc. PLAT431_ALERT_2_B Short Inter HL..A Contact I14 .. N13 = 3.06 Ang. PLAT431_ALERT_2_B Short Inter HL..A Contact I24 .. N23 = 3.14 Ang.
Alert level C PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound .. ? PLAT431_ALERT_2_C Short Inter HL..A Contact I24 .. Cl22 = 3.55 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl15 .. N13 = 3.10 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl16 .. N11 = 3.19 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl26 .. N21 = 3.13 Ang.
Alert level G CHEMS02_ALERT_1_G Please check that you have entered the correct _publ_requested_category classification of your compound; FI or CI or EI for inorganic; FM or CM or EM for metal-organic; FO or CO or EO for organic. From the CIF: _publ_requested_category EO From the CIF: _chemical_formula_sum :C8 Cl3 I1 N2 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.04 From the CIF: _reflns_number_total 1872 Count of symmetry unique reflns 1239 Completeness (_total/calc) 151.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 633 Fraction of Friedel pairs measured 0.511 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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
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. |
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