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The title compound, C16H12ClN3OS, is polymorphic. In the α form, a dihedral angle of 13.3 (1)° exists between the approximately planar phenyl­thia­zolehydrazine unit and the 4-chloro­phenol ring. Intra­molecular O—H...N hydrogen bonds are formed, and inter­molecular N—H...O and C—H...N inter­actions generate R22(8) motifs that link the mol­ecules into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040529/bi2071sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040529/bi2071Isup2.hkl
Contains datablock I

CCDC reference: 627321

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.087
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01 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 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: STOE X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-Chloro-2-[(4-phenyl-thiazol-2-yl)-hydrazonomethyl]-phenol top
Crystal data top
C16H12ClN3OSF(000) = 680
Mr = 329.80Dx = 1.491 Mg m3
Monoclinic, P21/cMelting point: 505 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.5776 (4) ÅCell parameters from 29319 reflections
b = 11.2455 (8) Åθ = 1.8–27.2°
c = 20.2612 (11) ŵ = 0.41 mm1
β = 101.400 (4)°T = 296 K
V = 1469.12 (16) Å3Prism, brown
Z = 40.60 × 0.37 × 0.14 mm
Data collection top
STOE IPDS2
diffractometer
2878 independent reflections
Radiation source: fine-focus sealed tube2237 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: integration
X-RED32 (Stoe & Cie, 2002)
h = 78
Tmin = 0.795, Tmax = 0.948k = 1313
19826 measured reflectionsl = 2424
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1526P]
where P = (Fo2 + 2Fc2)/3
2878 reflections(Δ/σ)max = 0.001
207 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.19 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
Cl11.29598 (8)0.14876 (5)0.13500 (3)0.05872 (17)
S10.30637 (8)0.41306 (4)0.34911 (3)0.05034 (16)
O10.6646 (2)0.44330 (12)0.22294 (9)0.0601 (4)
H10.608 (4)0.406 (2)0.2471 (13)0.071 (8)*
N10.1806 (2)0.21126 (13)0.38607 (8)0.0407 (3)
N20.4474 (2)0.19555 (14)0.32540 (9)0.0468 (4)
H90.440 (4)0.114 (2)0.3249 (12)0.074 (7)*
N30.5705 (2)0.25536 (13)0.28995 (8)0.0403 (3)
C10.0919 (3)0.26340 (16)0.44910 (9)0.0414 (4)
C20.2089 (3)0.34741 (18)0.47491 (11)0.0533 (5)
H20.18680.42780.46810.064*
C30.3580 (3)0.3137 (2)0.51059 (11)0.0588 (5)
H30.43420.37140.52800.071*
C40.3942 (3)0.1957 (2)0.52052 (11)0.0599 (6)
H40.49590.17320.54400.072*
C50.2795 (4)0.1109 (2)0.49552 (12)0.0630 (6)
H50.30330.03070.50230.076*
C60.1289 (3)0.14402 (18)0.46034 (11)0.0522 (5)
H60.05130.08580.44400.063*
C70.0661 (3)0.29879 (16)0.41033 (9)0.0396 (4)
C80.1130 (3)0.41104 (17)0.39508 (10)0.0489 (5)
H80.04890.47860.40780.059*
C90.3109 (3)0.25939 (15)0.35376 (9)0.0389 (4)
C100.7057 (3)0.19614 (15)0.26632 (9)0.0413 (4)
H100.72080.11520.27550.050*
C110.8363 (3)0.25266 (15)0.22540 (9)0.0386 (4)
C120.8131 (3)0.37222 (16)0.20539 (10)0.0430 (4)
C130.9408 (3)0.42126 (17)0.16617 (11)0.0517 (5)
H130.92570.50090.15390.062*
C141.0900 (3)0.35368 (17)0.14511 (10)0.0502 (5)
H141.17550.38720.11860.060*
C151.1118 (3)0.23566 (16)0.16357 (9)0.0428 (4)
C160.9888 (3)0.18569 (16)0.20375 (10)0.0421 (4)
H161.00780.10640.21660.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0484 (3)0.0627 (3)0.0745 (4)0.0049 (2)0.0351 (3)0.0062 (3)
S10.0565 (3)0.0372 (2)0.0655 (3)0.0028 (2)0.0321 (2)0.0012 (2)
O10.0727 (10)0.0390 (7)0.0826 (11)0.0122 (7)0.0493 (9)0.0100 (7)
N10.0397 (8)0.0377 (8)0.0496 (9)0.0018 (6)0.0209 (7)0.0017 (6)
N20.0472 (9)0.0365 (8)0.0657 (11)0.0034 (7)0.0331 (8)0.0009 (7)
N30.0375 (8)0.0393 (8)0.0493 (9)0.0043 (6)0.0210 (7)0.0018 (6)
C10.0389 (9)0.0475 (10)0.0401 (10)0.0006 (8)0.0136 (8)0.0031 (8)
C20.0565 (12)0.0504 (11)0.0600 (13)0.0034 (9)0.0287 (10)0.0041 (9)
C30.0541 (12)0.0676 (14)0.0634 (13)0.0067 (10)0.0327 (10)0.0061 (11)
C40.0505 (12)0.0775 (15)0.0600 (13)0.0054 (10)0.0315 (10)0.0008 (11)
C50.0643 (14)0.0582 (13)0.0759 (16)0.0070 (10)0.0367 (12)0.0034 (11)
C60.0548 (12)0.0482 (11)0.0609 (13)0.0013 (9)0.0294 (10)0.0012 (9)
C70.0378 (9)0.0413 (9)0.0421 (10)0.0000 (7)0.0135 (8)0.0049 (7)
C80.0544 (11)0.0391 (10)0.0608 (12)0.0031 (8)0.0299 (10)0.0027 (9)
C90.0386 (9)0.0371 (9)0.0443 (10)0.0033 (7)0.0160 (8)0.0035 (7)
C100.0407 (9)0.0357 (9)0.0519 (11)0.0003 (7)0.0196 (8)0.0007 (8)
C110.0376 (9)0.0382 (9)0.0426 (10)0.0033 (7)0.0143 (8)0.0029 (7)
C120.0460 (10)0.0379 (9)0.0496 (11)0.0030 (8)0.0202 (8)0.0018 (8)
C130.0616 (12)0.0396 (10)0.0608 (12)0.0002 (9)0.0290 (10)0.0069 (9)
C140.0523 (11)0.0510 (11)0.0542 (11)0.0052 (9)0.0274 (9)0.0044 (9)
C150.0368 (9)0.0486 (10)0.0467 (11)0.0001 (8)0.0173 (8)0.0060 (8)
C160.0401 (9)0.0395 (9)0.0504 (11)0.0009 (7)0.0177 (8)0.0003 (8)
Geometric parameters (Å, º) top
Cl1—C151.7421 (17)C4—C51.374 (3)
S1—C81.7189 (18)C4—H40.930
S1—C91.7305 (17)C5—C61.381 (3)
O1—C121.363 (2)C5—H50.930
O1—H10.79 (3)C6—H60.930
N1—C91.295 (2)C7—C81.350 (3)
N1—C71.387 (2)C8—H80.930
N2—N31.361 (2)C10—C111.453 (2)
N2—C91.362 (2)C10—H100.930
N2—H90.91 (3)C11—C161.393 (2)
N3—C101.278 (2)C11—C121.404 (2)
C1—C21.385 (2)C12—C131.380 (3)
C1—C61.391 (3)C13—C141.374 (3)
C1—C71.476 (2)C13—H130.930
C2—C31.381 (3)C14—C151.379 (3)
C2—H20.930C14—H140.930
C3—C41.370 (3)C15—C161.376 (2)
C3—H30.930C16—H160.930
C8—S1—C987.93 (8)C7—C8—S1111.32 (14)
C12—O1—H1107.1 (18)C7—C8—H8124.3
C9—N1—C7110.03 (15)S1—C8—H8124.3
N3—N2—C9118.19 (15)N1—C9—N2123.37 (16)
N3—N2—H9121.5 (15)N1—C9—S1116.03 (13)
C9—N2—H9119.6 (15)N2—C9—S1120.59 (13)
C10—N3—N2118.09 (15)N3—C10—C11121.32 (16)
C2—C1—C6117.91 (17)N3—C10—H10119.3
C2—C1—C7121.30 (17)C11—C10—H10119.3
C6—C1—C7120.78 (16)C16—C11—C12118.10 (16)
C3—C2—C1121.04 (19)C16—C11—C10119.15 (16)
C3—C2—H2119.5C12—C11—C10122.74 (15)
C1—C2—H2119.5O1—C12—C13117.71 (17)
C4—C3—C2120.29 (19)O1—C12—C11121.95 (16)
C4—C3—H3119.9C13—C12—C11120.33 (17)
C2—C3—H3119.9C14—C13—C12120.73 (18)
C3—C4—C5119.64 (19)C14—C13—H13119.6
C3—C4—H4120.2C12—C13—H13119.6
C5—C4—H4120.2C13—C14—C15119.37 (17)
C4—C5—C6120.4 (2)C13—C14—H14120.3
C4—C5—H5119.8C15—C14—H14120.3
C6—C5—H5119.8C16—C15—C14120.79 (16)
C5—C6—C1120.75 (19)C16—C15—Cl1119.75 (15)
C5—C6—H6119.6C14—C15—Cl1119.45 (14)
C1—C6—H6119.6C15—C16—C11120.65 (17)
C8—C7—N1114.68 (15)C15—C16—H16119.7
C8—C7—C1126.23 (16)C11—C16—H16119.7
N1—C7—C1119.09 (15)
C9—N2—N3—C10176.49 (17)N3—N2—C9—N1176.99 (17)
C6—C1—C2—C30.1 (3)N3—N2—C9—S14.0 (2)
C7—C1—C2—C3179.34 (19)C8—S1—C9—N10.30 (16)
C1—C2—C3—C40.7 (3)C8—S1—C9—N2178.80 (17)
C2—C3—C4—C50.8 (4)N2—N3—C10—C11177.19 (16)
C3—C4—C5—C60.2 (4)N3—C10—C11—C16176.66 (17)
C4—C5—C6—C10.5 (4)N3—C10—C11—C124.6 (3)
C2—C1—C6—C50.7 (3)C16—C11—C12—O1178.40 (18)
C7—C1—C6—C5178.7 (2)C10—C11—C12—O10.3 (3)
C9—N1—C7—C80.4 (2)C16—C11—C12—C130.9 (3)
C9—N1—C7—C1179.78 (16)C10—C11—C12—C13179.63 (19)
C2—C1—C7—C80.8 (3)O1—C12—C13—C14178.18 (19)
C6—C1—C7—C8178.6 (2)C11—C12—C13—C141.1 (3)
C2—C1—C7—N1179.40 (18)C12—C13—C14—C150.1 (3)
C6—C1—C7—N11.2 (3)C13—C14—C15—C161.2 (3)
N1—C7—C8—S10.2 (2)C13—C14—C15—Cl1178.23 (16)
C1—C7—C8—S1179.99 (15)C14—C15—C16—C111.5 (3)
C9—S1—C8—C70.05 (16)Cl1—C15—C16—C11178.00 (14)
C7—N1—C9—N2178.63 (17)C12—C11—C16—C150.4 (3)
C7—N1—C9—S10.4 (2)C10—C11—C16—C15178.39 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.79 (3)1.94 (3)2.651 (2)149 (2)
N2—H9···O1i0.91 (3)2.20 (3)3.044 (2)153 (2)
C13—H13···N1ii0.932.553.473 (2)170
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2.
 

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