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The steric demand of a tertiary alkyl substituent attached to the thio­hydroxamate O atom in the title compound, C13H15NOS2, is reflected in a widening of the associated N—O—C angle [116.4 (2)°]. Close contacts along [100] indicate C—H...S inter­actions in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038360/sj2119sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038360/sj2119Isup2.hkl
Contains datablock I

CCDC reference: 624990

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.085
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.20 Deg.
Author Response: Since the compound was prepared in a project that ended a few years ago, the meassurement was performed using the theta range that was routinely applied at that time. In view of the fact that the structure is an organic compound, which scatters with minor intensity at high theta values we feel that the presented structural information on this compound is reliable enough in order to unambigiously solve the structure and refine the structure model reliably.

Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5768 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.20 Deg. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. S2 .. 2.93 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL002_ALERT_1_A The contact author's address is missing, _publ_contact_author_address.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 1998); cell refinement: EXPOSE; data reduction: EXPOSE; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1994); software used to prepare material for publication: SHELXTL-Plus.

3-(1-Methyl-1-phenylethoxy)-1,3-thiazole-2(3H)-thione top
Crystal data top
C13H15NOS2F(000) = 560
Mr = 265.38Dx = 1.294 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.7504 (16) ÅCell parameters from 5396 reflections
b = 18.363 (4) Åθ = 2.2–24.2°
c = 9.788 (2) ŵ = 0.37 mm1
β = 102.16 (3)°T = 293 K
V = 1361.9 (5) Å3Prism, colourless
Z = 40.35 × 0.25 × 0.20 mm
Data collection top
Stoe IPDS
diffractometer
1278 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.090
Graphite monochromatorθmax = 24.2°, θmin = 2.2°
φ scansh = 88
10870 measured reflectionsk = 2121
2099 independent reflectionsl = 1010
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0355P)2]
where P = (Fo2 + 2Fc2)/3
2099 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (600 MHz, CDCl3, δ, p.p.m.): 1.52 (d, J = 1.1 Hz, 3H), 1.56 (s, 6H), 6.00 (d, J = 1.1 Hz, 1H), 7.32–7.34 (mc, 1H), 7.37–7.39 (mc, 2H), 7.55–7.56 (mc, 2H); 13C NMR (150 MHz, CDCl3, δ, p.p.m.): 14.9, 92.4, 102.4, 125.5, 128.2, 128.4, 140.1, 145.0, 184.3; IR (KBr, ν, cm-1): 3103, 2978, 1591, 1448, 1366, 1302, 1273, 1144, 1100, 1019; UV–vis (methanol): λ (lgε / m2 mol-1): 320 (3.12).

5396 quasi-centered reflections selected from the whole data were selected with the program SELECT 2.87 (Stoe, 1998) to determine the unit cell. For data collection, 167 exposures were taken in the 0–250.5 φ range with a crystal to detector distance of 80 mm and an exposure time of 3.50 minutes. Dynamic profiles (13–19 pixels) were used for integration. At least 50 reflections with I/s(I) > 6 taken from each frame were used to calculate the decay.

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*/UeqOcc. (<1)
S10.05856 (9)0.42736 (4)0.40161 (8)0.0582 (2)
O10.06957 (19)0.41044 (8)0.01508 (17)0.0436 (4)
S20.37305 (9)0.40749 (5)0.27429 (9)0.0695 (3)
C20.1576 (3)0.41465 (12)0.2618 (3)0.0444 (6)
N30.0275 (2)0.41269 (10)0.1441 (2)0.0415 (5)
C40.1455 (3)0.42650 (12)0.1604 (3)0.0448 (6)
C50.1477 (3)0.43484 (14)0.2936 (3)0.0567 (7)
H50.25010.44380.32620.085*
C60.2938 (3)0.43151 (15)0.0367 (3)0.0604 (7)
H6A0.25050.42270.04680.091*0.50
H6B0.34510.47930.03250.091*0.50
H6C0.38170.39580.04440.091*0.50
H6D0.40110.44250.06690.091*0.50
H6E0.30650.38590.01240.091*0.50
H6F0.26980.46940.02430.091*0.50
C70.0743 (3)0.33593 (13)0.0495 (3)0.0471 (6)
C80.0960 (4)0.27702 (14)0.0602 (3)0.0685 (9)
H8A0.20370.28480.12770.103*
H8B0.09980.23040.01670.103*
H8C0.00190.27840.10610.103*
C90.2375 (3)0.34231 (18)0.1127 (3)0.0757 (9)
H9A0.21910.37980.18260.114*
H9B0.25810.29680.15460.114*
H9C0.33790.35440.04060.114*
C100.0927 (3)0.32904 (12)0.1629 (3)0.0427 (6)
C110.1394 (3)0.38403 (14)0.2596 (3)0.0537 (7)
H110.06590.42430.25600.064*
C120.2918 (4)0.38095 (17)0.3610 (3)0.0671 (8)
H120.32240.41940.42330.081*
C130.3986 (4)0.32065 (18)0.3697 (3)0.0737 (9)
H130.50130.31790.43860.088*
C140.3539 (4)0.26538 (17)0.2778 (4)0.0730 (9)
H140.42540.22430.28470.088*
C150.2026 (4)0.26941 (14)0.1732 (3)0.0585 (7)
H150.17490.23150.10940.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0694 (5)0.0630 (4)0.0437 (5)0.0028 (3)0.0155 (3)0.0043 (3)
O10.0482 (9)0.0463 (10)0.0378 (11)0.0030 (7)0.0125 (7)0.0026 (7)
S20.0431 (4)0.0947 (6)0.0655 (6)0.0096 (4)0.0006 (3)0.0133 (4)
C20.0453 (14)0.0453 (15)0.0422 (17)0.0028 (11)0.0084 (11)0.0036 (11)
N30.0412 (11)0.0476 (13)0.0367 (14)0.0022 (9)0.0108 (9)0.0035 (9)
C40.0399 (13)0.0452 (14)0.0516 (19)0.0009 (11)0.0147 (12)0.0025 (12)
C50.0533 (16)0.0614 (17)0.061 (2)0.0008 (12)0.0234 (14)0.0074 (14)
C60.0410 (15)0.0744 (18)0.065 (2)0.0041 (13)0.0106 (13)0.0027 (15)
C70.0487 (15)0.0466 (15)0.0451 (18)0.0027 (11)0.0076 (12)0.0094 (12)
C80.086 (2)0.0490 (17)0.062 (2)0.0124 (14)0.0049 (16)0.0035 (14)
C90.0484 (17)0.109 (2)0.073 (2)0.0000 (16)0.0188 (15)0.0338 (19)
C100.0447 (14)0.0448 (15)0.0399 (17)0.0035 (11)0.0122 (11)0.0048 (12)
C110.0579 (17)0.0590 (17)0.0429 (19)0.0134 (12)0.0076 (13)0.0014 (13)
C120.0729 (19)0.078 (2)0.045 (2)0.0000 (17)0.0006 (14)0.0081 (15)
C130.0537 (18)0.090 (2)0.068 (2)0.0111 (16)0.0067 (15)0.0089 (19)
C140.0597 (19)0.067 (2)0.088 (3)0.0197 (15)0.0036 (17)0.0046 (18)
C150.0622 (18)0.0499 (16)0.062 (2)0.0045 (13)0.0101 (14)0.0024 (13)
Geometric parameters (Å, º) top
S1—C21.720 (3)C7—C91.524 (4)
S1—C51.727 (3)C8—H8A0.9600
O1—N31.370 (2)C8—H8B0.9600
O1—C71.511 (3)C8—H8C0.9600
S2—C21.654 (2)C9—H9A0.9600
C2—N31.362 (3)C9—H9B0.9600
N3—C41.406 (3)C9—H9C0.9600
C4—C51.317 (4)C10—C151.378 (3)
C4—C61.487 (4)C10—C111.379 (3)
C5—H50.9300C11—C121.375 (4)
C6—H6A0.9600C11—H110.9300
C6—H6B0.9600C12—C131.374 (4)
C6—H6C0.9600C12—H120.9300
C6—H6D0.9600C13—C141.352 (4)
C6—H6E0.9600C13—H130.9300
C6—H6F0.9600C14—C151.387 (4)
C7—C81.509 (4)C14—H140.9300
C7—C101.523 (3)C15—H150.9300
C2—S1—C591.99 (13)C8—C7—C10114.1 (2)
N3—O1—C7116.41 (16)O1—C7—C10106.76 (18)
N3—C2—S2128.04 (19)C8—C7—C9111.5 (2)
N3—C2—S1107.55 (16)O1—C7—C9101.28 (19)
S2—C2—S1124.40 (15)C10—C7—C9111.2 (2)
C2—N3—O1120.20 (18)C7—C8—H8A109.5
C2—N3—C4116.9 (2)C7—C8—H8B109.5
O1—N3—C4121.86 (19)H8A—C8—H8B109.5
C5—C4—N3110.2 (2)C7—C8—H8C109.5
C5—C4—C6129.0 (2)H8A—C8—H8C109.5
N3—C4—C6120.7 (2)H8B—C8—H8C109.5
C4—C5—S1113.1 (2)C7—C9—H9A109.5
C4—C5—H5123.4C7—C9—H9B109.5
S1—C5—H5123.4H9A—C9—H9B109.5
C4—C6—H6A109.5C7—C9—H9C109.5
C4—C6—H6B109.5H9A—C9—H9C109.5
H6A—C6—H6B109.5H9B—C9—H9C109.5
C4—C6—H6C109.5C15—C10—C11117.6 (2)
H6A—C6—H6C109.5C15—C10—C7122.5 (2)
H6B—C6—H6C109.5C11—C10—C7119.9 (2)
C4—C6—H6D109.5C12—C11—C10121.8 (2)
H6A—C6—H6D141.1C12—C11—H11119.1
H6B—C6—H6D56.3C10—C11—H11119.1
H6C—C6—H6D56.3C13—C12—C11119.5 (3)
C4—C6—H6E109.5C13—C12—H12120.3
H6A—C6—H6E56.3C11—C12—H12120.3
H6B—C6—H6E141.1C14—C13—C12119.8 (3)
H6C—C6—H6E56.3C14—C13—H13120.1
H6D—C6—H6E109.5C12—C13—H13120.1
C4—C6—H6F109.5C13—C14—C15120.6 (3)
H6A—C6—H6F56.3C13—C14—H14119.7
H6B—C6—H6F56.3C15—C14—H14119.7
H6C—C6—H6F141.1C10—C15—C14120.7 (3)
H6D—C6—H6F109.5C10—C15—H15119.7
H6E—C6—H6F109.5C14—C15—H15119.7
C8—C7—O1111.1 (2)
C5—S1—C2—N33.45 (18)N3—O1—C7—C10104.5 (2)
C5—S1—C2—S2175.86 (17)N3—O1—C7—C9139.0 (2)
S2—C2—N3—O15.9 (3)C8—C7—C10—C157.5 (3)
S1—C2—N3—O1173.41 (14)O1—C7—C10—C15130.7 (2)
S2—C2—N3—C4174.52 (17)C9—C7—C10—C15119.7 (3)
S1—C2—N3—C44.8 (2)C8—C7—C10—C11172.0 (2)
C7—O1—N3—C295.6 (2)O1—C7—C10—C1148.9 (3)
C7—O1—N3—C496.3 (2)C9—C7—C10—C1160.8 (3)
C2—N3—C4—C53.7 (3)C15—C10—C11—C121.5 (4)
O1—N3—C4—C5172.2 (2)C7—C10—C11—C12178.1 (3)
C2—N3—C4—C6175.0 (2)C10—C11—C12—C132.0 (4)
O1—N3—C4—C66.5 (3)C11—C12—C13—C140.7 (5)
N3—C4—C5—S10.8 (3)C12—C13—C14—C151.0 (5)
C6—C4—C5—S1177.8 (2)C11—C10—C15—C140.2 (4)
C2—S1—C5—C41.6 (2)C7—C10—C15—C14179.8 (3)
N3—O1—C7—C820.5 (3)C13—C14—C15—C101.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···S2i0.932.933.713 (3)142
Symmetry code: (i) x1, y, z.
 

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