The central CNC(=S)O entity in MeOC(=S)N(H)Ph, C
8H
9NOS, 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
CCDC reference: 221693
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (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
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.
Crystal data top
C8H9NOS | Z = 2 |
Mr = 167.22 | F(000) = 176 |
Triclinic, P1 | Dx = 1.342 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 5.8261 (4) Å | Cell parameters from 2429 reflections |
b = 8.3209 (5) Å | θ = 2.4–30.0° |
c = 9.6602 (6) Å | µ = 0.33 mm−1 |
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 tube | Rint = 0.020 |
Graphite monochromator | θmax = 30.0°, θmin = 2.4° |
ω scans | h = −4→8 |
3446 measured reflections | k = −11→11 |
2365 independent reflections | l = −12→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.30544 (5) | 0.13898 (4) | 0.32984 (3) | 0.03933 (12) | |
O1 | 0.43584 (15) | 0.30771 (11) | 0.47978 (10) | 0.0368 (2) | |
N1 | 0.10424 (18) | 0.15787 (14) | 0.59683 (12) | 0.0359 (2) | |
H1 | −0.0064 | 0.0946 | 0.5976 | 0.043* | |
C1 | 0.28310 (19) | 0.20305 (14) | 0.47483 (13) | 0.0301 (2) | |
C2 | 0.07654 (19) | 0.20352 (14) | 0.72708 (12) | 0.0307 (2) | |
C3 | 0.2424 (2) | 0.15048 (17) | 0.81988 (14) | 0.0375 (2) | |
H3 | 0.3776 | 0.0873 | 0.7959 | 0.045* | |
C4 | 0.2082 (2) | 0.19096 (18) | 0.94856 (14) | 0.0421 (3) | |
H4 | 0.3212 | 0.1557 | 1.0116 | 0.051* | |
C5 | 0.0104 (3) | 0.28228 (19) | 0.98431 (15) | 0.0450 (3) | |
H5 | −0.0118 | 0.3097 | 1.0715 | 0.054* | |
C6 | −0.1556 (3) | 0.3337 (2) | 0.89220 (18) | 0.0511 (3) | |
H6 | −0.2917 | 0.3953 | 0.9174 | 0.061* | |
C7 | −0.1234 (2) | 0.29514 (19) | 0.76248 (16) | 0.0427 (3) | |
H7 | −0.2364 | 0.3310 | 0.6994 | 0.051* | |
C8 | 0.6471 (2) | 0.35787 (19) | 0.36045 (16) | 0.0442 (3) | |
H8A | 0.7408 | 0.4338 | 0.3791 | 0.066* | |
H8B | 0.6051 | 0.4210 | 0.2594 | 0.066* | |
H8C | 0.7376 | 0.2526 | 0.3625 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.04375 (19) | 0.0494 (2) | 0.03336 (18) | −0.00461 (13) | −0.00479 (12) | −0.02573 (14) |
O1 | 0.0395 (4) | 0.0402 (4) | 0.0342 (4) | −0.0124 (3) | 0.0010 (3) | −0.0202 (3) |
N1 | 0.0343 (5) | 0.0464 (5) | 0.0356 (5) | −0.0095 (4) | −0.0017 (4) | −0.0256 (4) |
C1 | 0.0327 (5) | 0.0308 (5) | 0.0301 (5) | −0.0003 (4) | −0.0074 (4) | −0.0152 (4) |
C2 | 0.0332 (5) | 0.0326 (5) | 0.0290 (5) | −0.0071 (4) | −0.0007 (4) | −0.0163 (4) |
C3 | 0.0380 (6) | 0.0430 (6) | 0.0350 (6) | 0.0028 (5) | −0.0063 (4) | −0.0205 (5) |
C4 | 0.0491 (7) | 0.0486 (7) | 0.0316 (6) | −0.0032 (5) | −0.0091 (5) | −0.0182 (5) |
C5 | 0.0576 (8) | 0.0479 (7) | 0.0331 (6) | −0.0068 (6) | 0.0005 (5) | −0.0235 (5) |
C6 | 0.0501 (8) | 0.0590 (8) | 0.0493 (8) | 0.0100 (6) | −0.0020 (6) | −0.0336 (7) |
C7 | 0.0379 (6) | 0.0523 (7) | 0.0424 (6) | 0.0045 (5) | −0.0076 (5) | −0.0249 (6) |
C8 | 0.0408 (6) | 0.0494 (7) | 0.0403 (6) | −0.0151 (5) | 0.0034 (5) | −0.0190 (5) |
Geometric parameters (Å, º) top
S1—C1 | 1.6708 (11) | C4—C5 | 1.372 (2) |
O1—C1 | 1.3293 (13) | C4—H4 | 0.9400 |
O1—C8 | 1.4400 (15) | C5—C6 | 1.377 (2) |
N1—C1 | 1.3288 (15) | C5—H5 | 0.9400 |
N1—C2 | 1.4314 (13) | C6—C7 | 1.3877 (19) |
N1—H1 | 0.8700 | C6—H6 | 0.9400 |
C2—C7 | 1.3814 (17) | C7—H7 | 0.9400 |
C2—C3 | 1.3810 (17) | C8—H8A | 0.9700 |
C3—C4 | 1.3867 (16) | C8—H8B | 0.9700 |
C3—H3 | 0.9400 | C8—H8C | 0.9700 |
| | | |
C1—O1—C8 | 118.72 (9) | C6—C5—C4 | 119.88 (12) |
C1—N1—C2 | 126.10 (10) | C6—C5—H5 | 120.1 |
C1—N1—H1 | 116.9 | C4—C5—H5 | 120.1 |
C2—N1—H1 | 116.9 | C5—C6—C7 | 120.49 (12) |
S1—C1—O1 | 124.48 (8) | C5—C6—H6 | 119.8 |
S1—C1—N1 | 122.98 (9) | C7—C6—H6 | 119.8 |
O1—C1—N1 | 112.51 (9) | C2—C7—C6 | 119.27 (12) |
N1—C2—C7 | 119.02 (11) | C2—C7—H7 | 120.4 |
N1—C2—C3 | 120.52 (10) | C6—C7—H7 | 120.4 |
C3—C2—C7 | 120.41 (11) | O1—C8—H8A | 109.5 |
C4—C3—C2 | 119.60 (11) | O1—C8—H8B | 109.5 |
C4—C3—H3 | 120.2 | H8A—C8—H8B | 109.5 |
C2—C3—H3 | 120.2 | O1—C8—H8C | 109.5 |
C3—C4—C5 | 120.35 (12) | H8A—C8—H8C | 109.5 |
C3—C4—H4 | 119.8 | H8B—C8—H8C | 109.5 |
C5—C4—H4 | 119.8 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.87 | 2.51 | 3.3587 (12) | 165 |
Symmetry code: (i) −x, −y, −z+1. |