organic compounds
Phenyl N-(1,3-thiazol-2-yl)carbamate
aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and bDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 625 Dachang District Nanjing, Nanjing 210048, People's Republic of China
*Correspondence e-mail: guocheng@njut.edu.cn
In the title compound, C10H8N2O2S, the planes of the aromatic rings are oriented at a dihedral angle of 66.69 (3)°. In the intermolecular N—H⋯N and C—H⋯O interactions link the molecules into a two-dimensional network, forming R22(8) ring motifs. π–π contacts between the thiazole rings [centroid–centroid distance = 3.535 (1) Å] may further stabilize the structure. A weak C—H⋯π interaction is also found.
Related literature
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).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; 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 and PLATON.
Supporting information
10.1107/S1600536809020236/hk2701sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020236/hk2701Isup2.hkl
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.
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).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
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).C10H8N2O2S | F(000) = 456 |
Mr = 220.24 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 5.6430 (11) Å | θ = 9–13° |
b = 7.3910 (15) Å | µ = 0.29 mm−1 |
c = 25.134 (5) Å | T = 294 K |
β = 91.21 (3)° | Block, colorless |
V = 1048.0 (4) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1346 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.3°, θmin = 1.6° |
ω/2θ scans | h = 0→6 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→8 |
Tmin = 0.918, Tmax = 0.972 | l = −30→30 |
2084 measured reflections | 3 standard reflections every 120 min |
1880 independent reflections | intensity decay: 1% |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C10H8N2O2S | V = 1048.0 (4) Å3 |
Mr = 220.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.6430 (11) Å | µ = 0.29 mm−1 |
b = 7.3910 (15) Å | T = 294 K |
c = 25.134 (5) Å | 0.30 × 0.20 × 0.10 mm |
β = 91.21 (3)° |
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 = 0.972 | 3 standard reflections every 120 min |
2084 measured reflections | intensity decay: 1% |
1880 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.23 e Å−3 |
1880 reflections | Δρmin = −0.28 e Å−3 |
136 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S | 0.50888 (16) | 0.91653 (14) | 0.09893 (4) | 0.0578 (3) | |
O1 | −0.0749 (4) | 1.3216 (4) | 0.10691 (9) | 0.0584 (7) | |
O2 | 0.2490 (4) | 1.1925 (4) | 0.14685 (10) | 0.0604 (7) | |
N1 | 0.0988 (5) | 1.0912 (4) | 0.06773 (11) | 0.0522 (8) | |
H1A | −0.0156 | 1.1050 | 0.0449 | 0.063* | |
N2 | 0.2450 (5) | 0.8574 (4) | 0.01638 (11) | 0.0535 (8) | |
C1 | −0.1494 (7) | 1.7169 (6) | 0.22167 (16) | 0.0653 (11) | |
H1B | −0.1690 | 1.8072 | 0.2470 | 0.078* | |
C2 | −0.3070 (7) | 1.5775 (6) | 0.21820 (16) | 0.0700 (12) | |
H2B | −0.4336 | 1.5728 | 0.2413 | 0.084* | |
C3 | −0.2801 (6) | 1.4432 (5) | 0.18072 (15) | 0.0583 (10) | |
H3A | −0.3880 | 1.3484 | 0.1781 | 0.070* | |
C4 | −0.0921 (6) | 1.4522 (5) | 0.14755 (13) | 0.0476 (8) | |
C5 | 0.0675 (7) | 1.5907 (5) | 0.15058 (15) | 0.0592 (10) | |
H5A | 0.1945 | 1.5943 | 0.1276 | 0.071* | |
C6 | 0.0395 (8) | 1.7244 (6) | 0.18762 (16) | 0.0666 (11) | |
H6A | 0.1470 | 1.8196 | 0.1899 | 0.080* | |
C7 | 0.1061 (6) | 1.2010 (5) | 0.11072 (14) | 0.0494 (9) | |
C8 | 0.2638 (6) | 0.9587 (5) | 0.05834 (13) | 0.0446 (8) | |
C9 | 0.4328 (7) | 0.7386 (5) | 0.01506 (16) | 0.0617 (10) | |
H9A | 0.4494 | 0.6552 | −0.0123 | 0.074* | |
C10 | 0.5867 (7) | 0.7498 (6) | 0.05473 (17) | 0.0651 (11) | |
H10B | 0.7206 | 0.6772 | 0.0585 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0439 (5) | 0.0727 (7) | 0.0563 (6) | −0.0038 (5) | −0.0113 (4) | 0.0105 (5) |
O1 | 0.0530 (14) | 0.0639 (17) | 0.0574 (15) | 0.0055 (13) | −0.0160 (12) | −0.0165 (13) |
O2 | 0.0554 (15) | 0.0714 (18) | 0.0536 (15) | −0.0004 (13) | −0.0156 (12) | −0.0085 (13) |
N1 | 0.0431 (15) | 0.0635 (19) | 0.0493 (16) | 0.0000 (15) | −0.0130 (13) | −0.0135 (15) |
N2 | 0.0532 (17) | 0.0526 (17) | 0.0542 (17) | 0.0043 (15) | −0.0076 (14) | −0.0044 (15) |
C1 | 0.066 (3) | 0.072 (3) | 0.058 (2) | 0.010 (2) | −0.0082 (19) | −0.014 (2) |
C2 | 0.053 (2) | 0.094 (3) | 0.063 (2) | 0.003 (2) | 0.0069 (19) | −0.007 (2) |
C3 | 0.0443 (19) | 0.067 (3) | 0.064 (2) | −0.0096 (18) | −0.0019 (17) | −0.002 (2) |
C4 | 0.0482 (19) | 0.049 (2) | 0.0453 (19) | −0.0013 (16) | −0.0090 (15) | −0.0020 (16) |
C5 | 0.057 (2) | 0.065 (3) | 0.055 (2) | −0.011 (2) | 0.0101 (17) | −0.0055 (19) |
C6 | 0.072 (3) | 0.062 (2) | 0.066 (3) | −0.016 (2) | −0.003 (2) | −0.009 (2) |
C7 | 0.0454 (19) | 0.052 (2) | 0.051 (2) | −0.0129 (17) | −0.0057 (16) | −0.0003 (17) |
C8 | 0.0433 (18) | 0.0499 (19) | 0.0403 (18) | −0.0062 (16) | −0.0056 (14) | 0.0051 (15) |
C9 | 0.068 (2) | 0.056 (2) | 0.062 (2) | 0.007 (2) | −0.0016 (19) | −0.0001 (19) |
C10 | 0.054 (2) | 0.061 (2) | 0.080 (3) | 0.0108 (19) | 0.001 (2) | 0.017 (2) |
S—C10 | 1.722 (4) | C1—H1B | 0.9300 |
S—C8 | 1.729 (3) | C2—C3 | 1.379 (5) |
O1—C4 | 1.410 (4) | C2—H2B | 0.9300 |
O1—C7 | 1.358 (4) | C3—C4 | 1.364 (5) |
O2—C7 | 1.203 (4) | C3—H3A | 0.9300 |
N1—C7 | 1.351 (4) | C4—C5 | 1.365 (5) |
N1—C8 | 1.375 (4) | C5—C6 | 1.369 (5) |
N1—H1A | 0.8600 | C5—H5A | 0.9300 |
N2—C8 | 1.296 (4) | C6—H6A | 0.9300 |
N2—C9 | 1.377 (5) | C9—C10 | 1.311 (6) |
C1—C2 | 1.363 (6) | C9—H9A | 0.9300 |
C1—C6 | 1.382 (6) | C10—H10B | 0.9300 |
C10—S—C8 | 87.71 (18) | C4—C5—C6 | 119.6 (4) |
C7—O1—C4 | 117.5 (2) | C4—C5—H5A | 120.2 |
C7—N1—C8 | 123.7 (3) | C6—C5—H5A | 120.2 |
C7—N1—H1A | 118.1 | C5—C6—C1 | 119.6 (4) |
C8—N1—H1A | 118.1 | C5—C6—H6A | 120.2 |
C2—C1—C6 | 120.1 (4) | C1—C6—H6A | 120.2 |
C2—C1—H1B | 120.0 | O2—C7—N1 | 125.5 (3) |
C6—C1—H1B | 120.0 | O2—C7—O1 | 125.4 (3) |
C8—N2—C9 | 109.8 (3) | N1—C7—O1 | 109.1 (3) |
C1—C2—C3 | 120.4 (4) | N2—C8—N1 | 120.5 (3) |
C1—C2—H2B | 119.8 | N2—C8—S | 115.2 (3) |
C3—C2—H2B | 119.8 | N1—C8—S | 124.3 (2) |
C4—C3—C2 | 118.7 (4) | C10—C9—N2 | 116.0 (4) |
C4—C3—H3A | 120.6 | C10—C9—H9A | 122.0 |
C2—C3—H3A | 120.6 | N2—C9—H9A | 122.0 |
C3—C4—C5 | 121.5 (3) | C9—C10—S | 111.2 (3) |
C3—C4—O1 | 118.4 (3) | C9—C10—H10B | 124.4 |
C5—C4—O1 | 119.9 (3) | S—C10—H10B | 124.4 |
C6—C1—C2—C3 | −0.2 (6) | C4—O1—C7—O2 | 2.5 (5) |
C1—C2—C3—C4 | 0.5 (6) | C4—O1—C7—N1 | −178.0 (3) |
C2—C3—C4—C5 | −0.3 (6) | C9—N2—C8—N1 | 178.6 (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—N2 | 179.5 (3) |
C7—O1—C4—C5 | 72.1 (4) | C7—N1—C8—S | −1.8 (5) |
C3—C4—C5—C6 | −0.1 (6) | C10—S—C8—N2 | 0.1 (3) |
O1—C4—C5—C6 | 175.2 (3) | C10—S—C8—N1 | −178.6 (3) |
C4—C5—C6—C1 | 0.3 (6) | C8—N2—C9—C10 | 0.2 (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—C9 | 0.0 (3) |
C8—N1—C7—O1 | 177.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2i | 0.86 | 2.01 | 2.864 (4) | 171 |
C3—H3A···O2ii | 0.93 | 2.46 | 3.335 (4) | 156 |
C5—H5A···Cg2iii | 0.93 | 2.98 | 3.736 (3) | 139 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y, z; (iii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H8N2O2S |
Mr | 220.24 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 5.6430 (11), 7.3910 (15), 25.134 (5) |
β (°) | 91.21 (3) |
V (Å3) | 1048.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.918, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2084, 1880, 1346 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.160, 1.00 |
No. of reflections | 1880 |
No. of parameters | 136 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.28 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2i | 0.86 | 2.01 | 2.864 (4) | 171 |
C3—H3A···O2ii | 0.93 | 2.46 | 3.335 (4) | 156 |
C5—H5A···Cg2iii | 0.93 | 2.98 | 3.736 (3) | 139 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y, z; (iii) x, y+1, z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
References
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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).