Phenyl N-(1,3-thia­zol-2-yl)carbamate

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. 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

• C₁₀H₈N₂O₂S

• M_r = 220.24

• Monoclinic, P 2₁ /c

• a = 5.6430 (11) Å

• b = 7.3910 (15) Å

• c = 25.134 (5) Å

• β = 91.21 (3)°

• V = 1048.0 (4) ų

• Z = 4

• Mo Kα radiation

• μ = 0.29 mm⁻¹

• T = 294 K

• 0.30 × 0.20 × 0.10 mm

Data collection

• Enraf–Nonius CAD-4 diffractometer

• Absorption correction: ψ scan (North et al., 1968) T_min = 0.918, T_max = 0.972

• 2084 measured reflections

• 1880 independent reflections

• 1346 reflections with I > 2σ(I)

• R_int = 0.027

• 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

• R[F² > 2σ(F²)] = 0.050

• wR(F²) = 0.160

• S = 1.00

• 1880 reflections

• 136 parameters

• H-atom parameters constrained

• Δρ_max = 0.23 e Å⁻³

• Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2^i	0.86	2.01	2.864 (4)	171
C3—H3A⋯O2^ii	0.93	2.46	3.335 (4)	156
C5—H5A⋯Cg2^iii	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. Cg2 is the centroid of the S/N2/C8–C10 ring.

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: 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

S1. Comment

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

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.

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2U_eq(C,N).

Computing details

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

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	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

Crystal data

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) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 1.2P] where P = (Fo^2 + 2Fc^2)/3
1880 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2^i	0.86	2.01	2.864 (4)	171
C3—H3A···O2^ii	0.93	2.46	3.335 (4)	156
C5—H5A···Cg2^iii	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.