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The central CNC(=S)O entity in MeOC(=S)N(H)Ph, C8H9NOS, is effectively planar and shows that the mol­ecule exists as a thione. In the crystal structure, mol­ecules related by a centre of symmetry are associated via N—H...S interactions, forming thio­amide dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015435/su6033sup1.cif
Contains datablocks gobal, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015435/su6033Isup2.hkl
Contains datablock I

CCDC reference: 221693

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.108
  • Data-to-parameter ratio = 23.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHEXLTL.

(I) top
Crystal data top
C8H9NOSZ = 2
Mr = 167.22F(000) = 176
Triclinic, P1Dx = 1.342 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 5.8261 (4) ÅCell parameters from 2429 reflections
b = 8.3209 (5) Åθ = 2.4–30.0°
c = 9.6602 (6) ŵ = 0.33 mm1
α = 65.216 (2)°T = 223 K
β = 76.823 (2)°Block, colourless
γ = 84.066 (3)°0.55 × 0.42 × 0.30 mm
V = 413.97 (5) Å3
Data collection top
Bruker AXS SMART CCD
diffractometer
2128 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 30.0°, θmin = 2.4°
ω scansh = 48
3446 measured reflectionsk = 1111
2365 independent reflectionsl = 1213
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.0605P]
where P = (Fo2 + 2Fc2)/3
2365 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.33 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. The H atoms were introduced at calculated positions as riding atoms, with bond lengths of 0.87(N—H), 0.94(CH-aromatic), and 0.97(CH3) Å. The displacement parameters were made equal to 1.2(CH, NH) or 1.5(CH3) times thoses of the parent atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.30544 (5)0.13898 (4)0.32984 (3)0.03933 (12)
O10.43584 (15)0.30771 (11)0.47978 (10)0.0368 (2)
N10.10424 (18)0.15787 (14)0.59683 (12)0.0359 (2)
H10.00640.09460.59760.043*
C10.28310 (19)0.20305 (14)0.47483 (13)0.0301 (2)
C20.07654 (19)0.20352 (14)0.72708 (12)0.0307 (2)
C30.2424 (2)0.15048 (17)0.81988 (14)0.0375 (2)
H30.37760.08730.79590.045*
C40.2082 (2)0.19096 (18)0.94856 (14)0.0421 (3)
H40.32120.15571.01160.051*
C50.0104 (3)0.28228 (19)0.98431 (15)0.0450 (3)
H50.01180.30971.07150.054*
C60.1556 (3)0.3337 (2)0.89220 (18)0.0511 (3)
H60.29170.39530.91740.061*
C70.1234 (2)0.29514 (19)0.76248 (16)0.0427 (3)
H70.23640.33100.69940.051*
C80.6471 (2)0.35787 (19)0.36045 (16)0.0442 (3)
H8A0.74080.43380.37910.066*
H8B0.60510.42100.25940.066*
H8C0.73760.25260.36250.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.04375 (19)0.0494 (2)0.03336 (18)0.00461 (13)0.00479 (12)0.02573 (14)
O10.0395 (4)0.0402 (4)0.0342 (4)0.0124 (3)0.0010 (3)0.0202 (3)
N10.0343 (5)0.0464 (5)0.0356 (5)0.0095 (4)0.0017 (4)0.0256 (4)
C10.0327 (5)0.0308 (5)0.0301 (5)0.0003 (4)0.0074 (4)0.0152 (4)
C20.0332 (5)0.0326 (5)0.0290 (5)0.0071 (4)0.0007 (4)0.0163 (4)
C30.0380 (6)0.0430 (6)0.0350 (6)0.0028 (5)0.0063 (4)0.0205 (5)
C40.0491 (7)0.0486 (7)0.0316 (6)0.0032 (5)0.0091 (5)0.0182 (5)
C50.0576 (8)0.0479 (7)0.0331 (6)0.0068 (6)0.0005 (5)0.0235 (5)
C60.0501 (8)0.0590 (8)0.0493 (8)0.0100 (6)0.0020 (6)0.0336 (7)
C70.0379 (6)0.0523 (7)0.0424 (6)0.0045 (5)0.0076 (5)0.0249 (6)
C80.0408 (6)0.0494 (7)0.0403 (6)0.0151 (5)0.0034 (5)0.0190 (5)
Geometric parameters (Å, º) top
S1—C11.6708 (11)C4—C51.372 (2)
O1—C11.3293 (13)C4—H40.9400
O1—C81.4400 (15)C5—C61.377 (2)
N1—C11.3288 (15)C5—H50.9400
N1—C21.4314 (13)C6—C71.3877 (19)
N1—H10.8700C6—H60.9400
C2—C71.3814 (17)C7—H70.9400
C2—C31.3810 (17)C8—H8A0.9700
C3—C41.3867 (16)C8—H8B0.9700
C3—H30.9400C8—H8C0.9700
C1—O1—C8118.72 (9)C6—C5—C4119.88 (12)
C1—N1—C2126.10 (10)C6—C5—H5120.1
C1—N1—H1116.9C4—C5—H5120.1
C2—N1—H1116.9C5—C6—C7120.49 (12)
S1—C1—O1124.48 (8)C5—C6—H6119.8
S1—C1—N1122.98 (9)C7—C6—H6119.8
O1—C1—N1112.51 (9)C2—C7—C6119.27 (12)
N1—C2—C7119.02 (11)C2—C7—H7120.4
N1—C2—C3120.52 (10)C6—C7—H7120.4
C3—C2—C7120.41 (11)O1—C8—H8A109.5
C4—C3—C2119.60 (11)O1—C8—H8B109.5
C4—C3—H3120.2H8A—C8—H8B109.5
C2—C3—H3120.2O1—C8—H8C109.5
C3—C4—C5120.35 (12)H8A—C8—H8C109.5
C3—C4—H4119.8H8B—C8—H8C109.5
C5—C4—H4119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.872.513.3587 (12)165
Symmetry code: (i) x, y, z+1.
 

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