Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033076/lh6520sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033076/lh6520Isup2.hkl |
CCDC reference: 289807
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.003 Å
- R factor = 0.021
- wR factor = 0.056
- Data-to-parameter ratio = 20.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.07 PLAT431_ALERT_2_C Short Inter HL..A Contact I1 .. N1 .. 3.23 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2001).
C14H10I2N2 | F(000) = 856 |
Mr = 460.04 | Dx = 2.159 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 879 reflections |
a = 16.262 (4) Å | θ = 2.6–28.3° |
b = 4.7074 (11) Å | µ = 4.43 mm−1 |
c = 18.708 (4) Å | T = 193 K |
β = 98.829 (4)° | Tabular, yellow |
V = 1415.2 (6) Å3 | 0.34 × 0.24 × 0.06 mm |
Z = 4 |
Siemens Platform CCD area-detector diffractometer | 1760 independent reflections |
Radiation source: normal-focus sealed tube | 1607 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Profile data from ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: integration (XPREP in SHELXTL; Bruker, 2001) | h = −21→21 |
Tmin = 0.295, Tmax = 0.771 | k = −6→6 |
6991 measured reflections | l = −24→24 |
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)] = 0.021 | H-atom parameters constrained |
wR(F2) = 0.056 | w = 1/[σ2(Fo2) + (0.0295P)2 + 1.6495P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
1760 reflections | Δρmax = 0.72 e Å−3 |
88 parameters | Δρmin = −0.79 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Bruker, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (2) |
Experimental. One distinct cell was identified using SMART (Bruker, 2001). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied. |
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. Systematic conditions suggested the ambiguous space group. Structure was phased by direct methods. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The highest peak in the final difference Fourier map was in the vicinity of atom I1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.03012 (13) | 0.5940 (5) | 0.52037 (12) | 0.0298 (5) | |
H1 | 0.0858 | 0.5914 | 0.5107 | 0.095 (13)* | |
C2 | 0.07114 (13) | 0.9415 (5) | 0.60663 (11) | 0.0283 (4) | |
C3 | 0.15177 (14) | 0.9815 (5) | 0.59080 (13) | 0.0322 (5) | |
H3 | 0.1700 | 0.8788 | 0.5524 | 0.053 (8)* | |
C4 | 0.20477 (13) | 1.1712 (5) | 0.63129 (12) | 0.0275 (4) | |
C5 | 0.17915 (16) | 1.3240 (5) | 0.68736 (13) | 0.0338 (5) | |
H5 | 0.2157 | 1.4550 | 0.7147 | 0.038 (7)* | |
C6 | 0.09907 (19) | 1.2823 (5) | 0.70278 (15) | 0.0388 (6) | |
H6 | 0.0810 | 1.3847 | 0.7413 | 0.049 (8)* | |
C7 | 0.04556 (14) | 1.0938 (5) | 0.66277 (12) | 0.0314 (5) | |
H7 | −0.0091 | 1.0682 | 0.6737 | 0.039 (7)* | |
I1 | 0.325791 (9) | 1.22825 (4) | 0.607495 (9) | 0.03758 (10) | |
N1 | 0.01194 (15) | 0.7582 (4) | 0.56736 (15) | 0.0438 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0242 (10) | 0.0308 (11) | 0.0345 (12) | −0.0052 (9) | 0.0046 (9) | −0.0054 (9) |
C2 | 0.0266 (10) | 0.0289 (10) | 0.0296 (11) | −0.0066 (8) | 0.0046 (8) | −0.0053 (8) |
C3 | 0.0278 (10) | 0.0346 (11) | 0.0355 (12) | −0.0065 (9) | 0.0084 (9) | −0.0107 (9) |
C4 | 0.0252 (11) | 0.0271 (10) | 0.0298 (11) | −0.0034 (8) | 0.0023 (8) | 0.0015 (8) |
C5 | 0.0355 (12) | 0.0360 (11) | 0.0288 (11) | −0.0104 (10) | 0.0015 (9) | −0.0079 (9) |
C6 | 0.0406 (15) | 0.0433 (14) | 0.0340 (13) | −0.0096 (10) | 0.0110 (11) | −0.0150 (10) |
C7 | 0.0294 (11) | 0.0359 (12) | 0.0299 (11) | −0.0069 (9) | 0.0076 (9) | −0.0061 (9) |
I1 | 0.02493 (12) | 0.04507 (13) | 0.04290 (14) | −0.01160 (6) | 0.00572 (7) | −0.00591 (6) |
N1 | 0.0263 (11) | 0.0552 (15) | 0.0528 (15) | −0.0174 (8) | 0.0148 (10) | −0.0272 (10) |
C1—N1 | 1.240 (3) | C4—C5 | 1.388 (3) |
C1—C1i | 1.447 (4) | C4—I1 | 2.101 (2) |
C1—H1 | 0.9500 | C5—C6 | 1.390 (4) |
C2—C7 | 1.387 (3) | C5—H5 | 0.9500 |
C2—C3 | 1.401 (3) | C6—C7 | 1.380 (3) |
C2—N1 | 1.412 (3) | C6—H6 | 0.9500 |
C3—C4 | 1.383 (3) | C7—H7 | 0.9500 |
C3—H3 | 0.9500 | ||
N1—C1—C1i | 122.6 (3) | C5—C4—I1 | 119.59 (16) |
N1—C1—H1 | 118.7 | C4—C5—C6 | 118.9 (2) |
C1i—C1—H1 | 118.7 | C4—C5—H5 | 120.6 |
C7—C2—C3 | 119.3 (2) | C6—C5—H5 | 120.6 |
C7—C2—N1 | 116.7 (2) | C7—C6—C5 | 120.7 (2) |
C3—C2—N1 | 123.9 (2) | C7—C6—H6 | 119.6 |
C4—C3—C2 | 119.7 (2) | C5—C6—H6 | 119.6 |
C4—C3—H3 | 120.1 | C6—C7—C2 | 120.4 (2) |
C2—C3—H3 | 120.1 | C6—C7—H7 | 119.8 |
C3—C4—C5 | 121.0 (2) | C2—C7—H7 | 119.8 |
C3—C4—I1 | 119.45 (17) | C1—N1—C2 | 122.1 (2) |
C7—C2—C3—C4 | 0.1 (4) | C5—C6—C7—C2 | 0.3 (4) |
N1—C2—C3—C4 | 178.4 (2) | C3—C2—C7—C6 | −0.2 (4) |
C2—C3—C4—C5 | −0.3 (4) | N1—C2—C7—C6 | −178.6 (2) |
C2—C3—C4—I1 | 179.68 (17) | C1i—C1—N1—C2 | −179.8 (3) |
C3—C4—C5—C6 | 0.4 (4) | C7—C2—N1—C1 | −173.6 (3) |
I1—C4—C5—C6 | −179.5 (2) | C3—C2—N1—C1 | 8.1 (4) |
C4—C5—C6—C7 | −0.5 (4) |
Symmetry code: (i) −x, −y+1, −z+1. |