Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048811/fb2027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048811/fb2027Isup2.hkl |
CCDC reference: 629661
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.030
- wR factor = 0.072
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 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 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
C13H9IN2S | F(000) = 680 |
Mr = 352.18 | Dx = 1.857 Mg m−3 |
Monoclinic, P21/c | Melting point: 422 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8023 (3) Å | Cell parameters from 954 reflections |
b = 8.7783 (4) Å | θ = 3.2–22.9° |
c = 18.5532 (10) Å | µ = 2.69 mm−1 |
β = 97.446 (4)° | T = 296 K |
V = 1260.01 (10) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.13 × 0.09 mm |
Bruker SMART APEX-II CCD diffractometer | 2199 independent reflections |
Radiation source: fine-focus sealed tube | 1552 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.1°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.658, Tmax = 0.785 | k = −9→10 |
4249 measured reflections | l = −18→22 |
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)] = 0.030 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0357P)2] where P = (Fo2 + 2Fc2)/3 |
2199 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
27 constraints |
Experimental. IR (KBr, ν cm-1): 3447, 3356, 1396, 1614, 1476, 756; 1H NMR (500 MHz, acetone-d6): δ 8.41408–8.41021 (d, 1H, J = 1.9 Hz), 8.02665–7.85033 (m, 3H), 7.51907–7.35840 (m, 3H), 6.98092–6.96402 (d, 2H, J = 12.5 Hz); 13C NMR (500 MHz, acetone-d6): δ 206.26, 137.79, 128.79, 126.32, 124.80, 122.34, 121.73, 113.89, 49.67, 29.47, 29.31, 29.25, 29.16, 29.00, 28.85, 28.70, 28.54; MS (m/z), calculated for C13H9IN2S+: 351.95; found: 352.00; analysis calculated for C13H9IN2S: C 44.33, H 2.58, N 7.95%; found: C 44.70, H 2.70, N 7.94%. |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. In this refinement, five diffractions were omitted because their observed intensitys were substantially lower than their calculated intensitys. The data are as follows. h, k, l, Fc-squared, Fo-squared, σ(Fo-squared) -2 2 4 29145.47 0.35 15.41 - 1 1 2 19708.18 - 2.26 7.31 - 1 3 4 3126.06 - 0.96 13.93 - 1 2 3 251.25 - 1.65 11.75 2 7 2 1339.60 630.13 55.79 If this five diffractions were not omitted, the result would have R1 = 0.0342 for 1547 Fo > 4sig(Fo) and 0.0605 for all data wR2 = 0.1448, GooF = S = 1.026, Restrained GooF = 1.026 for all data |
x | y | z | Uiso*/Ueq | ||
I1 | 0.37134 (3) | −0.20344 (4) | 0.303992 (18) | 0.05423 (14) | |
S1 | 0.82571 (14) | 0.17787 (14) | 0.49079 (6) | 0.0476 (3) | |
N1 | 1.0882 (4) | 0.1957 (4) | 0.41890 (19) | 0.0439 (9) | |
N2 | 0.6422 (5) | −0.2425 (5) | 0.1863 (2) | 0.0533 (11) | |
H2A | 0.7015 | −0.2614 | 0.1513 | 0.064* | |
H2B | 0.5409 | −0.2814 | 0.1858 | 0.064* | |
C1 | 0.7087 (5) | −0.1510 (5) | 0.2423 (2) | 0.0384 (10) | |
C2 | 0.6202 (5) | −0.1143 (5) | 0.3015 (2) | 0.0357 (10) | |
C3 | 0.6923 (5) | −0.0246 (5) | 0.3573 (2) | 0.0382 (10) | |
H3 | 0.6312 | −0.0058 | 0.3962 | 0.046* | |
C4 | 0.8557 (5) | 0.0396 (5) | 0.3573 (2) | 0.0379 (10) | |
C5 | 0.9433 (5) | 0.0042 (5) | 0.2982 (2) | 0.0417 (11) | |
H5 | 1.0529 | 0.0446 | 0.2965 | 0.050* | |
C6 | 0.8735 (5) | −0.0868 (5) | 0.2438 (2) | 0.0416 (11) | |
H6 | 0.9369 | −0.1077 | 0.2058 | 0.050* | |
C7 | 0.9352 (5) | 0.1372 (5) | 0.4164 (2) | 0.0366 (10) | |
C8 | 1.0018 (5) | 0.2842 (5) | 0.5290 (2) | 0.0442 (11) | |
C9 | 1.0250 (6) | 0.3655 (6) | 0.5939 (3) | 0.0561 (13) | |
H9 | 0.9375 | 0.3718 | 0.6234 | 0.067* | |
C10 | 1.1795 (6) | 0.4353 (6) | 0.6129 (3) | 0.0570 (13) | |
H10 | 1.1988 | 0.4877 | 0.6568 | 0.068* | |
C11 | 1.3089 (6) | 0.4306 (6) | 0.5686 (3) | 0.0567 (14) | |
H11 | 1.4131 | 0.4800 | 0.5831 | 0.068* | |
C12 | 1.2860 (6) | 0.3544 (6) | 0.5036 (3) | 0.0527 (13) | |
H12 | 1.3731 | 0.3529 | 0.4738 | 0.063* | |
C13 | 1.1297 (5) | 0.2786 (5) | 0.4829 (2) | 0.0412 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.03449 (17) | 0.0672 (3) | 0.0617 (2) | −0.00867 (16) | 0.00886 (13) | −0.00200 (19) |
S1 | 0.0406 (6) | 0.0574 (9) | 0.0466 (7) | −0.0078 (5) | 0.0127 (5) | −0.0046 (6) |
N1 | 0.0392 (19) | 0.055 (3) | 0.039 (2) | −0.0046 (19) | 0.0100 (15) | 0.004 (2) |
N2 | 0.049 (2) | 0.059 (3) | 0.053 (3) | −0.010 (2) | 0.0122 (19) | −0.021 (2) |
C1 | 0.040 (2) | 0.032 (2) | 0.043 (3) | 0.0064 (19) | 0.0035 (19) | 0.005 (2) |
C2 | 0.031 (2) | 0.033 (2) | 0.043 (3) | −0.0007 (19) | 0.0037 (18) | 0.004 (2) |
C3 | 0.037 (2) | 0.043 (3) | 0.037 (3) | 0.001 (2) | 0.0139 (18) | 0.004 (2) |
C4 | 0.036 (2) | 0.039 (3) | 0.039 (3) | 0.005 (2) | 0.0053 (18) | 0.005 (2) |
C5 | 0.033 (2) | 0.040 (3) | 0.053 (3) | −0.002 (2) | 0.010 (2) | 0.006 (2) |
C6 | 0.037 (2) | 0.048 (3) | 0.043 (3) | 0.004 (2) | 0.0147 (19) | 0.000 (2) |
C7 | 0.037 (2) | 0.035 (2) | 0.038 (3) | 0.000 (2) | 0.0086 (18) | 0.007 (2) |
C8 | 0.043 (2) | 0.050 (3) | 0.040 (3) | 0.001 (2) | 0.0036 (19) | 0.006 (2) |
C9 | 0.057 (3) | 0.061 (3) | 0.051 (3) | −0.001 (3) | 0.011 (2) | 0.001 (3) |
C10 | 0.065 (3) | 0.058 (4) | 0.046 (3) | −0.007 (3) | −0.003 (2) | 0.000 (3) |
C11 | 0.055 (3) | 0.048 (3) | 0.062 (4) | −0.012 (2) | −0.013 (2) | 0.008 (3) |
C12 | 0.041 (3) | 0.059 (3) | 0.057 (3) | −0.015 (2) | 0.003 (2) | 0.010 (3) |
C13 | 0.041 (2) | 0.043 (3) | 0.039 (3) | 0.001 (2) | 0.0032 (18) | 0.012 (2) |
I1—C2 | 2.100 (4) | C4—C7 | 1.465 (6) |
S1—C8 | 1.735 (5) | C5—C6 | 1.346 (6) |
S1—C7 | 1.752 (4) | C5—H5 | 0.9300 |
N1—C7 | 1.294 (5) | C6—H6 | 0.9300 |
N1—C13 | 1.395 (6) | C8—C9 | 1.392 (6) |
N2—C1 | 1.362 (5) | C8—C13 | 1.397 (6) |
N2—H2A | 0.8600 | C9—C10 | 1.357 (6) |
N2—H2B | 0.8600 | C9—H9 | 0.9300 |
C1—C6 | 1.401 (6) | C10—C11 | 1.382 (7) |
C1—C2 | 1.409 (6) | C10—H10 | 0.9300 |
C2—C3 | 1.362 (5) | C11—C12 | 1.370 (7) |
C3—C4 | 1.394 (5) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.398 (6) |
C4—C5 | 1.400 (6) | C12—H12 | 0.9300 |
C8—S1—C7 | 89.5 (2) | C1—C6—H6 | 118.8 |
C7—N1—C13 | 110.5 (4) | N1—C7—C4 | 124.0 (4) |
C1—N2—H2A | 120.0 | N1—C7—S1 | 115.6 (3) |
C1—N2—H2B | 120.0 | C4—C7—S1 | 120.4 (3) |
H2A—N2—H2B | 120.0 | C9—C8—C13 | 121.6 (4) |
N2—C1—C6 | 120.7 (4) | C9—C8—S1 | 129.6 (4) |
N2—C1—C2 | 123.6 (4) | C13—C8—S1 | 108.8 (3) |
C6—C1—C2 | 115.7 (4) | C10—C9—C8 | 117.9 (5) |
C3—C2—C1 | 121.9 (4) | C10—C9—H9 | 121.1 |
C3—C2—I1 | 119.4 (3) | C8—C9—H9 | 121.1 |
C1—C2—I1 | 118.7 (3) | C9—C10—C11 | 121.7 (5) |
C2—C3—C4 | 121.4 (4) | C9—C10—H10 | 119.2 |
C2—C3—H3 | 119.3 | C11—C10—H10 | 119.2 |
C4—C3—H3 | 119.3 | C12—C11—C10 | 121.0 (4) |
C3—C4—C5 | 116.7 (4) | C12—C11—H11 | 119.5 |
C3—C4—C7 | 122.4 (4) | C10—C11—H11 | 119.5 |
C5—C4—C7 | 120.9 (4) | C11—C12—C13 | 118.9 (5) |
C6—C5—C4 | 121.9 (4) | C11—C12—H12 | 120.5 |
C6—C5—H5 | 119.1 | C13—C12—H12 | 120.5 |
C4—C5—H5 | 119.1 | N1—C13—C12 | 125.5 (4) |
C5—C6—C1 | 122.3 (4) | N1—C13—C8 | 115.7 (4) |
C5—C6—H6 | 118.8 | C12—C13—C8 | 118.8 (4) |
N2—C1—C2—C3 | 178.7 (4) | C5—C4—C7—S1 | −178.9 (3) |
C6—C1—C2—C3 | −1.3 (6) | C8—S1—C7—N1 | 0.2 (4) |
N2—C1—C2—I1 | −0.4 (6) | C8—S1—C7—C4 | 178.7 (4) |
C6—C1—C2—I1 | 179.5 (3) | C7—S1—C8—C9 | 179.2 (5) |
C1—C2—C3—C4 | 2.1 (7) | C7—S1—C8—C13 | −0.7 (4) |
I1—C2—C3—C4 | −178.7 (3) | C13—C8—C9—C10 | −2.5 (7) |
C2—C3—C4—C5 | −1.6 (6) | S1—C8—C9—C10 | 177.6 (4) |
C2—C3—C4—C7 | 179.5 (4) | C8—C9—C10—C11 | 1.9 (8) |
C3—C4—C5—C6 | 0.3 (6) | C9—C10—C11—C12 | −0.2 (8) |
C7—C4—C5—C6 | 179.2 (4) | C10—C11—C12—C13 | −1.0 (7) |
C4—C5—C6—C1 | 0.4 (7) | C7—N1—C13—C12 | 178.8 (4) |
N2—C1—C6—C5 | −180.0 (4) | C7—N1—C13—C8 | −1.1 (5) |
C2—C1—C6—C5 | 0.0 (6) | C11—C12—C13—N1 | −179.5 (4) |
C13—N1—C7—C4 | −178.0 (4) | C11—C12—C13—C8 | 0.4 (7) |
C13—N1—C7—S1 | 0.5 (5) | C9—C8—C13—N1 | −178.7 (4) |
C3—C4—C7—N1 | 178.3 (4) | S1—C8—C13—N1 | 1.2 (5) |
C5—C4—C7—N1 | −0.5 (7) | C9—C8—C13—C12 | 1.4 (7) |
C3—C4—C7—S1 | 0.0 (6) | S1—C8—C13—C12 | −178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···I1 | 0.86 | 2.79 | 3.248 (4) | 115 |
N2—H2A···N1i | 0.86 | 2.26 | 3.097 (5) | 166 |
C3—H3···S1 | 0.93 | 2.70 | 3.116 (4) | 108 |
Symmetry code: (i) −x+2, y−1/2, −z+1/2. |