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The mol­ecules of the title compound, C16H10N2OS, are nearly planar. An intra­molecular O—H...N and an inter­molecular C—H...O hydrogen bond are obseved in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003187/bt6808sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003187/bt6808Isup2.hkl
Contains datablock I

CCDC reference: 601122

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.093
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 5.17 su 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-(1,3-Benzothiazol-2-yl)quinolin-8-ol top
Crystal data top
C16H10N2OSF(000) = 1152
Mr = 278.32Dx = 1.445 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 12.182 (2) Åθ = 6.5–21.1°
b = 8.0602 (8) ŵ = 2.21 mm1
c = 26.061 (3) ÅT = 299 K
β = 91.53 (1)°Prism, light brown
V = 2558.0 (6) Å30.35 × 0.20 × 0.13 mm
Z = 8
Data collection top
Nonius CAD-4
diffractometer
1918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 66.9°, θmin = 3.4°
ω/2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 93
Tmin = 0.626, Tmax = 0.760l = 3131
3228 measured reflections3 standard reflections every 120 min
2282 independent reflections intensity decay: 1.0%
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)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.093Only H-atom coordinates refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0497P)2 + 1.0455P]
where P = (Fo2 + 2Fc2)/3
2282 reflections(Δ/σ)max = 0.011
211 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.97659 (15)0.2074 (2)0.56967 (6)0.0462 (4)
C21.04133 (18)0.1079 (3)0.60251 (8)0.0575 (5)
H21.0968 (19)0.037 (3)0.5890 (8)0.069*
C31.0230 (2)0.1197 (3)0.65445 (8)0.0650 (6)
H31.067 (2)0.054 (3)0.6755 (9)0.078*
C40.9434 (2)0.2243 (3)0.67355 (7)0.0627 (5)
H40.9324 (19)0.224 (3)0.7090 (9)0.075*
C50.88015 (18)0.3216 (3)0.64157 (7)0.0581 (5)
H50.8222 (18)0.396 (3)0.6550 (8)0.070*
C60.89675 (15)0.3139 (2)0.58861 (6)0.0462 (4)
C70.87326 (14)0.3693 (2)0.50653 (6)0.0420 (4)
C80.83004 (13)0.4465 (2)0.45900 (6)0.0403 (4)
C90.74770 (15)0.5679 (2)0.46110 (7)0.0483 (4)
H90.7186 (16)0.595 (3)0.4918 (8)0.058*
C100.71043 (16)0.6408 (3)0.41677 (7)0.0523 (4)
H100.6552 (18)0.726 (3)0.4175 (8)0.063*
C110.75360 (14)0.5913 (2)0.36952 (6)0.0455 (4)
C120.71965 (17)0.6566 (3)0.32108 (7)0.0569 (5)
H120.6625 (19)0.738 (3)0.3185 (9)0.068*
C130.76649 (17)0.6001 (3)0.27776 (7)0.0576 (5)
H130.7414 (18)0.643 (3)0.2446 (8)0.069*
C140.84841 (17)0.4787 (3)0.27916 (7)0.0534 (5)
H140.8815 (17)0.440 (3)0.2497 (9)0.064*
C150.88262 (15)0.4133 (2)0.32517 (7)0.0477 (4)
C160.83552 (13)0.4680 (2)0.37141 (6)0.0400 (4)
N10.83896 (12)0.40537 (19)0.55180 (5)0.0473 (4)
N20.87380 (11)0.39696 (18)0.41573 (5)0.0420 (3)
O10.96119 (14)0.2945 (2)0.32766 (6)0.0728 (5)
H1O0.968 (2)0.271 (3)0.3576 (10)0.087*
S10.97763 (4)0.22194 (6)0.503487 (16)0.04881 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0542 (10)0.0466 (10)0.0377 (9)0.0068 (8)0.0037 (7)0.0003 (7)
C20.0662 (12)0.0561 (12)0.0495 (10)0.0026 (10)0.0108 (9)0.0033 (9)
C30.0818 (15)0.0639 (13)0.0479 (11)0.0094 (11)0.0206 (10)0.0092 (10)
C40.0847 (14)0.0667 (13)0.0363 (10)0.0114 (12)0.0053 (9)0.0012 (9)
C50.0730 (13)0.0646 (13)0.0367 (9)0.0045 (10)0.0036 (8)0.0043 (9)
C60.0556 (10)0.0464 (10)0.0365 (8)0.0078 (8)0.0018 (7)0.0008 (7)
C70.0469 (9)0.0430 (9)0.0363 (8)0.0047 (7)0.0019 (6)0.0001 (7)
C80.0429 (8)0.0425 (9)0.0355 (8)0.0031 (7)0.0014 (6)0.0008 (7)
C90.0527 (10)0.0537 (11)0.0388 (9)0.0044 (8)0.0068 (7)0.0037 (8)
C100.0520 (10)0.0560 (11)0.0492 (10)0.0137 (9)0.0066 (8)0.0019 (9)
C110.0449 (9)0.0496 (10)0.0419 (9)0.0010 (8)0.0014 (7)0.0037 (8)
C120.0561 (11)0.0657 (12)0.0489 (10)0.0112 (10)0.0002 (8)0.0112 (9)
C130.0644 (12)0.0679 (13)0.0403 (9)0.0028 (10)0.0039 (8)0.0093 (9)
C140.0643 (11)0.0617 (12)0.0344 (9)0.0016 (9)0.0051 (8)0.0013 (8)
C150.0536 (10)0.0488 (10)0.0408 (9)0.0032 (8)0.0032 (7)0.0024 (8)
C160.0430 (8)0.0413 (8)0.0356 (8)0.0038 (7)0.0014 (6)0.0001 (7)
N10.0554 (8)0.0503 (9)0.0362 (7)0.0013 (7)0.0035 (6)0.0013 (6)
N20.0460 (7)0.0430 (8)0.0370 (7)0.0010 (6)0.0014 (6)0.0002 (6)
O10.0911 (11)0.0802 (11)0.0478 (8)0.0382 (9)0.0127 (8)0.0010 (8)
S10.0554 (3)0.0539 (3)0.0372 (2)0.0074 (2)0.00228 (17)0.00048 (19)
Geometric parameters (Å, º) top
C1—C61.397 (3)C9—C101.363 (3)
C1—C21.400 (3)C9—H90.91 (2)
C1—S11.7292 (17)C10—C111.409 (2)
C2—C31.381 (3)C10—H100.96 (2)
C2—H20.96 (2)C11—C161.408 (2)
C3—C41.388 (3)C11—C121.419 (2)
C3—H30.92 (3)C12—C131.357 (3)
C4—C51.367 (3)C12—H120.96 (2)
C4—H40.94 (2)C13—C141.398 (3)
C5—C61.402 (2)C13—H130.97 (2)
C5—H51.00 (2)C14—C151.365 (2)
C6—N11.387 (2)C14—H140.93 (2)
C7—N11.295 (2)C15—O11.354 (2)
C7—C81.471 (2)C15—C161.419 (2)
C7—S11.7431 (18)C16—N21.360 (2)
C8—N21.322 (2)O1—H1O0.81 (3)
C8—C91.404 (3)
C6—C1—C2121.46 (17)C8—C9—H9119.8 (13)
C6—C1—S1109.52 (13)C9—C10—C11119.68 (17)
C2—C1—S1129.01 (15)C9—C10—H10120.6 (12)
C3—C2—C1117.2 (2)C11—C10—H10119.7 (12)
C3—C2—H2122.4 (14)C16—C11—C10116.71 (15)
C1—C2—H2120.4 (14)C16—C11—C12118.83 (16)
C2—C3—C4121.8 (2)C10—C11—C12124.46 (18)
C2—C3—H3116.1 (15)C13—C12—C11119.78 (19)
C4—C3—H3122.1 (15)C13—C12—H12119.5 (14)
C5—C4—C3121.18 (19)C11—C12—H12120.7 (14)
C5—C4—H4120.8 (15)C12—C13—C14121.93 (18)
C3—C4—H4118.0 (15)C12—C13—H13119.5 (13)
C4—C5—C6118.8 (2)C14—C13—H13118.6 (13)
C4—C5—H5121.6 (13)C15—C14—C13119.63 (17)
C6—C5—H5119.7 (13)C15—C14—H14117.8 (14)
N1—C6—C1115.33 (14)C13—C14—H14122.5 (14)
N1—C6—C5125.00 (18)O1—C15—C14120.93 (17)
C1—C6—C5119.67 (17)O1—C15—C16118.71 (16)
N1—C7—C8123.72 (16)C14—C15—C16120.36 (17)
N1—C7—S1116.61 (13)N2—C16—C11123.60 (15)
C8—C7—S1119.67 (12)N2—C16—C15116.94 (15)
N2—C8—C9123.28 (15)C11—C16—C15119.46 (15)
N2—C8—C7116.57 (15)C7—N1—C6109.91 (15)
C9—C8—C7120.15 (15)C8—N2—C16117.41 (15)
C10—C9—C8119.32 (16)C15—O1—H1O106 (2)
C10—C9—H9120.9 (13)C1—S1—C788.63 (8)
C6—C1—C2—C30.0 (3)C12—C13—C14—C150.4 (3)
S1—C1—C2—C3179.57 (16)C13—C14—C15—O1179.44 (19)
C1—C2—C3—C40.5 (3)C13—C14—C15—C160.0 (3)
C2—C3—C4—C50.6 (4)C10—C11—C16—N20.2 (3)
C3—C4—C5—C60.2 (3)C12—C11—C16—N2179.84 (17)
C2—C1—C6—N1179.83 (16)C10—C11—C16—C15179.75 (17)
S1—C1—C6—N10.6 (2)C12—C11—C16—C150.6 (3)
C2—C1—C6—C50.3 (3)O1—C15—C16—N20.5 (3)
S1—C1—C6—C5179.28 (15)C14—C15—C16—N2179.93 (17)
C4—C5—C6—N1179.92 (18)O1—C15—C16—C11179.91 (17)
C4—C5—C6—C10.3 (3)C14—C15—C16—C110.5 (3)
N1—C7—C8—N2179.74 (16)C8—C7—N1—C6179.06 (15)
S1—C7—C8—N20.5 (2)S1—C7—N1—C60.22 (19)
N1—C7—C8—C90.7 (3)C1—C6—N1—C70.2 (2)
S1—C7—C8—C9178.58 (14)C5—C6—N1—C7179.60 (18)
N2—C8—C9—C100.5 (3)C9—C8—N2—C160.4 (3)
C7—C8—C9—C10178.53 (17)C7—C8—N2—C16179.45 (14)
C8—C9—C10—C111.1 (3)C11—C16—N2—C80.7 (2)
C9—C10—C11—C160.7 (3)C15—C16—N2—C8179.67 (15)
C9—C10—C11—C12178.9 (2)C6—C1—S1—C70.54 (14)
C16—C11—C12—C130.2 (3)C2—C1—S1—C7179.89 (19)
C10—C11—C12—C13179.9 (2)N1—C7—S1—C10.46 (14)
C11—C12—C13—C140.2 (3)C8—C7—S1—C1178.85 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N20.81 (3)2.18 (3)2.6859 (19)121 (2)
C12—H12···O1i0.96 (2)2.51 (2)3.348 (3)145.6 (18)
Symmetry code: (i) x1/2, y+1/2, z.
 

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