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The title mol­ecule, C13H9IN2S, is composed of two planar units, namely a substituted amino­phenyl ring and a benzothia­zole ring system. The maximum deviations from the mean planes fitted through the ring atoms are only 0.010 (5) and 0.027 (6) Å for the amino­phenyl and benzothia­zole, respectively. In the solid state, the I atom lies on the same side of the mol­ecule as the S atom rather than the N atom of the thiazole ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048811/fb2027sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048811/fb2027Isup2.hkl
Contains datablock I

CCDC reference: 629661

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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.

2-(4-Amino-3-iodophenyl)-1,3-benzothiazole top
Crystal data top
C13H9IN2SF(000) = 680
Mr = 352.18Dx = 1.857 Mg m3
Monoclinic, P21/cMelting point: 422 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.8023 (3) ÅCell parameters from 954 reflections
b = 8.7783 (4) Åθ = 3.2–22.9°
c = 18.5532 (10) ŵ = 2.69 mm1
β = 97.446 (4)°T = 296 K
V = 1260.01 (10) Å3Prism, colourless
Z = 40.30 × 0.13 × 0.09 mm
Data collection top
Bruker SMART APEX-II CCD
diffractometer
2199 independent reflections
Radiation source: fine-focus sealed tube1552 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.1°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.658, Tmax = 0.785k = 910
4249 measured reflectionsl = 1822
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.072H-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 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.37 e Å3
27 constraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.37134 (3)0.20344 (4)0.303992 (18)0.05423 (14)
S10.82571 (14)0.17787 (14)0.49079 (6)0.0476 (3)
N11.0882 (4)0.1957 (4)0.41890 (19)0.0439 (9)
N20.6422 (5)0.2425 (5)0.1863 (2)0.0533 (11)
H2A0.70150.26140.15130.064*
H2B0.54090.28140.18580.064*
C10.7087 (5)0.1510 (5)0.2423 (2)0.0384 (10)
C20.6202 (5)0.1143 (5)0.3015 (2)0.0357 (10)
C30.6923 (5)0.0246 (5)0.3573 (2)0.0382 (10)
H30.63120.00580.39620.046*
C40.8557 (5)0.0396 (5)0.3573 (2)0.0379 (10)
C50.9433 (5)0.0042 (5)0.2982 (2)0.0417 (11)
H51.05290.04460.29650.050*
C60.8735 (5)0.0868 (5)0.2438 (2)0.0416 (11)
H60.93690.10770.20580.050*
C70.9352 (5)0.1372 (5)0.4164 (2)0.0366 (10)
C81.0018 (5)0.2842 (5)0.5290 (2)0.0442 (11)
C91.0250 (6)0.3655 (6)0.5939 (3)0.0561 (13)
H90.93750.37180.62340.067*
C101.1795 (6)0.4353 (6)0.6129 (3)0.0570 (13)
H101.19880.48770.65680.068*
C111.3089 (6)0.4306 (6)0.5686 (3)0.0567 (14)
H111.41310.48000.58310.068*
C121.2860 (6)0.3544 (6)0.5036 (3)0.0527 (13)
H121.37310.35290.47380.063*
C131.1297 (5)0.2786 (5)0.4829 (2)0.0412 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03449 (17)0.0672 (3)0.0617 (2)0.00867 (16)0.00886 (13)0.00200 (19)
S10.0406 (6)0.0574 (9)0.0466 (7)0.0078 (5)0.0127 (5)0.0046 (6)
N10.0392 (19)0.055 (3)0.039 (2)0.0046 (19)0.0100 (15)0.004 (2)
N20.049 (2)0.059 (3)0.053 (3)0.010 (2)0.0122 (19)0.021 (2)
C10.040 (2)0.032 (2)0.043 (3)0.0064 (19)0.0035 (19)0.005 (2)
C20.031 (2)0.033 (2)0.043 (3)0.0007 (19)0.0037 (18)0.004 (2)
C30.037 (2)0.043 (3)0.037 (3)0.001 (2)0.0139 (18)0.004 (2)
C40.036 (2)0.039 (3)0.039 (3)0.005 (2)0.0053 (18)0.005 (2)
C50.033 (2)0.040 (3)0.053 (3)0.002 (2)0.010 (2)0.006 (2)
C60.037 (2)0.048 (3)0.043 (3)0.004 (2)0.0147 (19)0.000 (2)
C70.037 (2)0.035 (2)0.038 (3)0.000 (2)0.0086 (18)0.007 (2)
C80.043 (2)0.050 (3)0.040 (3)0.001 (2)0.0036 (19)0.006 (2)
C90.057 (3)0.061 (3)0.051 (3)0.001 (3)0.011 (2)0.001 (3)
C100.065 (3)0.058 (4)0.046 (3)0.007 (3)0.003 (2)0.000 (3)
C110.055 (3)0.048 (3)0.062 (4)0.012 (2)0.013 (2)0.008 (3)
C120.041 (3)0.059 (3)0.057 (3)0.015 (2)0.003 (2)0.010 (3)
C130.041 (2)0.043 (3)0.039 (3)0.001 (2)0.0032 (18)0.012 (2)
Geometric parameters (Å, º) top
I1—C22.100 (4)C4—C71.465 (6)
S1—C81.735 (5)C5—C61.346 (6)
S1—C71.752 (4)C5—H50.9300
N1—C71.294 (5)C6—H60.9300
N1—C131.395 (6)C8—C91.392 (6)
N2—C11.362 (5)C8—C131.397 (6)
N2—H2A0.8600C9—C101.357 (6)
N2—H2B0.8600C9—H90.9300
C1—C61.401 (6)C10—C111.382 (7)
C1—C21.409 (6)C10—H100.9300
C2—C31.362 (5)C11—C121.370 (7)
C3—C41.394 (5)C11—H110.9300
C3—H30.9300C12—C131.398 (6)
C4—C51.400 (6)C12—H120.9300
C8—S1—C789.5 (2)C1—C6—H6118.8
C7—N1—C13110.5 (4)N1—C7—C4124.0 (4)
C1—N2—H2A120.0N1—C7—S1115.6 (3)
C1—N2—H2B120.0C4—C7—S1120.4 (3)
H2A—N2—H2B120.0C9—C8—C13121.6 (4)
N2—C1—C6120.7 (4)C9—C8—S1129.6 (4)
N2—C1—C2123.6 (4)C13—C8—S1108.8 (3)
C6—C1—C2115.7 (4)C10—C9—C8117.9 (5)
C3—C2—C1121.9 (4)C10—C9—H9121.1
C3—C2—I1119.4 (3)C8—C9—H9121.1
C1—C2—I1118.7 (3)C9—C10—C11121.7 (5)
C2—C3—C4121.4 (4)C9—C10—H10119.2
C2—C3—H3119.3C11—C10—H10119.2
C4—C3—H3119.3C12—C11—C10121.0 (4)
C3—C4—C5116.7 (4)C12—C11—H11119.5
C3—C4—C7122.4 (4)C10—C11—H11119.5
C5—C4—C7120.9 (4)C11—C12—C13118.9 (5)
C6—C5—C4121.9 (4)C11—C12—H12120.5
C6—C5—H5119.1C13—C12—H12120.5
C4—C5—H5119.1N1—C13—C12125.5 (4)
C5—C6—C1122.3 (4)N1—C13—C8115.7 (4)
C5—C6—H6118.8C12—C13—C8118.8 (4)
N2—C1—C2—C3178.7 (4)C5—C4—C7—S1178.9 (3)
C6—C1—C2—C31.3 (6)C8—S1—C7—N10.2 (4)
N2—C1—C2—I10.4 (6)C8—S1—C7—C4178.7 (4)
C6—C1—C2—I1179.5 (3)C7—S1—C8—C9179.2 (5)
C1—C2—C3—C42.1 (7)C7—S1—C8—C130.7 (4)
I1—C2—C3—C4178.7 (3)C13—C8—C9—C102.5 (7)
C2—C3—C4—C51.6 (6)S1—C8—C9—C10177.6 (4)
C2—C3—C4—C7179.5 (4)C8—C9—C10—C111.9 (8)
C3—C4—C5—C60.3 (6)C9—C10—C11—C120.2 (8)
C7—C4—C5—C6179.2 (4)C10—C11—C12—C131.0 (7)
C4—C5—C6—C10.4 (7)C7—N1—C13—C12178.8 (4)
N2—C1—C6—C5180.0 (4)C7—N1—C13—C81.1 (5)
C2—C1—C6—C50.0 (6)C11—C12—C13—N1179.5 (4)
C13—N1—C7—C4178.0 (4)C11—C12—C13—C80.4 (7)
C13—N1—C7—S10.5 (5)C9—C8—C13—N1178.7 (4)
C3—C4—C7—N1178.3 (4)S1—C8—C13—N11.2 (5)
C5—C4—C7—N10.5 (7)C9—C8—C13—C121.4 (7)
C3—C4—C7—S10.0 (6)S1—C8—C13—C12178.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···I10.862.793.248 (4)115
N2—H2A···N1i0.862.263.097 (5)166
C3—H3···S10.932.703.116 (4)108
Symmetry code: (i) x+2, y1/2, z+1/2.
 

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