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Acta Cryst. (2009). E65, o1478    [ doi:10.1107/S1600536809020236 ]

Phenyl N-(1,3-thiazol-2-yl)carbamate

J.-G. Tang, Y.-Z. Wu, S. Bi, G.-H. Zhang and C. Guo

Abstract top

In the title compound, C10H8N2O2S, the planes of the aromatic rings are oriented at a dihedral angle of 66.69 (3)°. In the crystal structure, intermolecular N-H...N and C-H...O interactions link the molecules into a two-dimensional network, forming R22(8) ring motifs. [pi]-[pi] contacts between the thiazole rings [centroid-centroid distance = 3.535 (1) Å] may further stabilize the structure. A weak C-H...[pi] interaction is also found.

Comment top

Some derivatives of phenol are important chemical materials. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (S/N2/C8-C10) are, of course, planar and they are oriented at a dihedral angle of 66.69 (3)°. Atoms O1, O2, N1, C4, C7, H1A, H9A and H10B are 0.118 (3), -0.063 (3), 0.028 (3), 0.172 (3), 0.023 (3), 0.051 (3), 0.002 (3) and -0.002 (3) Å away from the plane of ring B, respectively.

In the crystal structure, intermolecular N-H···N and C-H···O interactions (Table 1) link the molecules into a two-dimensional network forming R22(8) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the thiazole rings, Cg2—Cg2i, [symmetry code: (i) 1 - x, -y, -z, where Cg2 is centroid of the ring B (S/N2/C8-C10)] may further stabilize the structure, with centroid-centroid distance of 3.535 (1) Å. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For a related structure, see: Araujo et al. (2006). For bond-length data, see: Allen et al. (1987). For ring-motifs, see: Bernstein et al. (1995). Cg2 is the centroid of the S/N2/C8–C10 ring B.

Experimental top

For the preparation of the title compound, phenyl chloroformate (1.0 ml) was added slowly to a cold solution of thiazol-2-amine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) at 273 K. The mixture was then warmed and stirred for 1 h at room temperature. Then, it was washed with water (20 ml), dried and concentrated to give the title compound (yield; 1.3 g) (Araujo et al., 2006). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Refinement top

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 Å for aromatic H and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
Phenyl N-(1,3-thiazol-2-yl)carbamate top
Crystal data top
C10H8N2O2SF(000) = 456
Mr = 220.24Dx = 1.396 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 5.6430 (11) Åθ = 9–13°
b = 7.3910 (15) ŵ = 0.29 mm−1
c = 25.134 (5) ÅT = 294 K
β = 91.21 (3)°Block, colorless
V = 1048.0 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		1346 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
graphiteθmax = 25.3°, θmin = 1.6°
ω/2θ scansh = 0→6
Absorption correction: ψ scan
(North et al., 1968)		k = 0→8
Tmin = 0.918, Tmax = 0.972l = −30→30
2084 measured reflections3 standard reflections every 120 min
1880 independent reflections intensity decay: 1%
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.07P)2 + 1.2P]
where P = (Fo2 + 2Fc2)/3
1880 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C10H8N2O2SV = 1048.0 (4) Å3
Mr = 220.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.6430 (11) ŵ = 0.29 mm−1
b = 7.3910 (15) ÅT = 294 K
c = 25.134 (5) Å0.30 × 0.20 × 0.10 mm
β = 91.21 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1346 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.027
Tmin = 0.918, Tmax = 0.972θmax = 25.3°
2084 measured reflections3 standard reflections every 120 min
1880 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.160Δρmax = 0.23 e Å−3
S = 1.00Δρmin = −0.28 e Å−3
1880 reflectionsAbsolute structure: ?
136 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
S0.50888 (16)0.91653 (14)0.09893 (4)0.0578 (3)
O1−0.0749 (4)1.3216 (4)0.10691 (9)0.0584 (7)
O20.2490 (4)1.1925 (4)0.14685 (10)0.0604 (7)
N10.0988 (5)1.0912 (4)0.06773 (11)0.0522 (8)
H1A−0.01561.10500.04490.063*
N20.2450 (5)0.8574 (4)0.01638 (11)0.0535 (8)
C1−0.1494 (7)1.7169 (6)0.22167 (16)0.0653 (11)
H1B−0.16901.80720.24700.078*
C2−0.3070 (7)1.5775 (6)0.21820 (16)0.0700 (12)
H2B−0.43361.57280.24130.084*
C3−0.2801 (6)1.4432 (5)0.18072 (15)0.0583 (10)
H3A−0.38801.34840.17810.070*
C4−0.0921 (6)1.4522 (5)0.14755 (13)0.0476 (8)
C50.0675 (7)1.5907 (5)0.15058 (15)0.0592 (10)
H5A0.19451.59430.12760.071*
C60.0395 (8)1.7244 (6)0.18762 (16)0.0666 (11)
H6A0.14701.81960.18990.080*
C70.1061 (6)1.2010 (5)0.11072 (14)0.0494 (9)
C80.2638 (6)0.9587 (5)0.05834 (13)0.0446 (8)
C90.4328 (7)0.7386 (5)0.01506 (16)0.0617 (10)
H9A0.44940.6552−0.01230.074*
C100.5867 (7)0.7498 (6)0.05473 (17)0.0651 (11)
H10B0.72060.67720.05850.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0439 (5)0.0727 (7)0.0563 (6)−0.0038 (5)−0.0113 (4)0.0105 (5)
O10.0530 (14)0.0639 (17)0.0574 (15)0.0055 (13)−0.0160 (12)−0.0165 (13)
O20.0554 (15)0.0714 (18)0.0536 (15)−0.0004 (13)−0.0156 (12)−0.0085 (13)
N10.0431 (15)0.0635 (19)0.0493 (16)0.0000 (15)−0.0130 (13)−0.0135 (15)
N20.0532 (17)0.0526 (17)0.0542 (17)0.0043 (15)−0.0076 (14)−0.0044 (15)
C10.066 (3)0.072 (3)0.058 (2)0.010 (2)−0.0082 (19)−0.014 (2)
C20.053 (2)0.094 (3)0.063 (2)0.003 (2)0.0069 (19)−0.007 (2)
C30.0443 (19)0.067 (3)0.064 (2)−0.0096 (18)−0.0019 (17)−0.002 (2)
C40.0482 (19)0.049 (2)0.0453 (19)−0.0013 (16)−0.0090 (15)−0.0020 (16)
C50.057 (2)0.065 (3)0.055 (2)−0.011 (2)0.0101 (17)−0.0055 (19)
C60.072 (3)0.062 (2)0.066 (3)−0.016 (2)−0.003 (2)−0.009 (2)
C70.0454 (19)0.052 (2)0.051 (2)−0.0129 (17)−0.0057 (16)−0.0003 (17)
C80.0433 (18)0.0499 (19)0.0403 (18)−0.0062 (16)−0.0056 (14)0.0051 (15)
C90.068 (2)0.056 (2)0.062 (2)0.007 (2)−0.0016 (19)−0.0001 (19)
C100.054 (2)0.061 (2)0.080 (3)0.0108 (19)0.001 (2)0.017 (2)
Geometric parameters (Å, °) top
S—C101.722 (4)C1—H1B0.9300
S—C81.729 (3)C2—C31.379 (5)
O1—C41.410 (4)C2—H2B0.9300
O1—C71.358 (4)C3—C41.364 (5)
O2—C71.203 (4)C3—H3A0.9300
N1—C71.351 (4)C4—C51.365 (5)
N1—C81.375 (4)C5—C61.369 (5)
N1—H1A0.8600C5—H5A0.9300
N2—C81.296 (4)C6—H6A0.9300
N2—C91.377 (5)C9—C101.311 (6)
C1—C21.363 (6)C9—H9A0.9300
C1—C61.382 (6)C10—H10B0.9300
C10—S—C887.71 (18)C4—C5—C6119.6 (4)
C7—O1—C4117.5 (2)C4—C5—H5A120.2
C7—N1—C8123.7 (3)C6—C5—H5A120.2
C7—N1—H1A118.1C5—C6—C1119.6 (4)
C8—N1—H1A118.1C5—C6—H6A120.2
C2—C1—C6120.1 (4)C1—C6—H6A120.2
C2—C1—H1B120.0O2—C7—N1125.5 (3)
C6—C1—H1B120.0O2—C7—O1125.4 (3)
C8—N2—C9109.8 (3)N1—C7—O1109.1 (3)
C1—C2—C3120.4 (4)N2—C8—N1120.5 (3)
C1—C2—H2B119.8N2—C8—S115.2 (3)
C3—C2—H2B119.8N1—C8—S124.3 (2)
C4—C3—C2118.7 (4)C10—C9—N2116.0 (4)
C4—C3—H3A120.6C10—C9—H9A122.0
C2—C3—H3A120.6N2—C9—H9A122.0
C3—C4—C5121.5 (3)C9—C10—S111.2 (3)
C3—C4—O1118.4 (3)C9—C10—H10B124.4
C5—C4—O1119.9 (3)S—C10—H10B124.4
C6—C1—C2—C3−0.2 (6)C4—O1—C7—O22.5 (5)
C1—C2—C3—C40.5 (6)C4—O1—C7—N1−178.0 (3)
C2—C3—C4—C5−0.3 (6)C9—N2—C8—N1178.6 (3)
C2—C3—C4—O1−175.6 (3)C9—N2—C8—S−0.2 (4)
C7—O1—C4—C3−112.5 (4)C7—N1—C8—N2179.5 (3)
C7—O1—C4—C572.1 (4)C7—N1—C8—S−1.8 (5)
C3—C4—C5—C6−0.1 (6)C10—S—C8—N20.1 (3)
O1—C4—C5—C6175.2 (3)C10—S—C8—N1−178.6 (3)
C4—C5—C6—C10.3 (6)C8—N2—C9—C100.2 (5)
C2—C1—C6—C5−0.2 (6)N2—C9—C10—S−0.2 (5)
C8—N1—C7—O2−3.3 (6)C8—S—C10—C90.0 (3)
C8—N1—C7—O1177.2 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.012.864 (4)171
C3—H3A···O2ii0.932.463.335 (4)156
C5—H5A···Cg2iii0.932.983.736 (3)139
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y, z; (iii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.012.864 (4)171
C3—H3A···O2ii0.932.463.335 (4)156
C5—H5A···Cg2iii0.932.983.736 (3)139
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y, z; (iii) x, y+1, z.
Acknowledgements top

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

references
References top

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