3-(2-Methyl-amino-1,3-thia-zol-4-yl)-2H-chromen-2-one.

In the title compound, C(13)H(10)N(2)O(2)S, the essentially planar 2H-chromene ring system [maximum deviation = 0.0297 (13) Å] and the thia-zole ring [maximum deviation = 0.0062 (11) Å] form a dihedral angle of 3.47 (5)°. In the crystal, N-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into two-dimensional networks parallel to the bc plane. C-H⋯π and π-π [centroid-centroid separation = 3.6796 (8) Å] inter-actions further stabilize the crystal structure.

Related literature

For the biological activities of coumarin derivatives, see: Soine (1964 ▶); Wattenberg et al. (1979 ▶); Jung et al. (1999 ▶); Rao et al. (1981 ▶). For a related structure, see: Arshad et al. (2010 ▶, 2011 ▶); Asad et al. (2011 ▶); Yusufzai, Osman, Sulaiman et al. (2012 ▶); Yusufzai, Osman, Abdul Rahim et al. (2012 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H10N2O2S

M = 258.29

Monoclinic,

a = 14.5460 (3) Å

b = 4.9289 (1) Å

c = 18.3516 (3) Å

β = 120.307 (1)°

V = 1135.92 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.47 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.881, T max = 0.946

13265 measured reflections

3303 independent reflections

2851 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.05

3303 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030140/rz2775sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030140/rz2775Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030140/rz2775Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H10N2O2S	F(000) = 536
Mr = 258.29	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7338 reflections
a = 14.5460 (3) Å	θ = 2.6–32.5°
b = 4.9289 (1) Å	µ = 0.28 mm−1
c = 18.3516 (3) Å	T = 100 K
β = 120.307 (1)°	Block, orange
V = 1135.92 (4) Å3	0.47 × 0.40 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3303 independent reflections
Radiation source: fine-focus sealed tube	2851 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→16
Tmin = 0.881, Tmax = 0.946	k = −6→6
13265 measured reflections	l = −25→25

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.5573P] where P = (Fo2 + 2Fc2)/3
3303 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.86394 (2)	0.35198 (6)	0.510226 (18)	0.01927 (9)
O1	0.59607 (7)	1.21689 (19)	0.55233 (5)	0.02025 (19)
O2	0.62018 (7)	1.0170 (2)	0.45629 (6)	0.0226 (2)
N1	0.87142 (8)	0.5208 (2)	0.64688 (6)	0.0167 (2)
N2	0.99500 (9)	0.1750 (2)	0.66837 (7)	0.0209 (2)
C1	0.61748 (9)	1.2526 (3)	0.63378 (7)	0.0174 (2)
C2	0.56079 (10)	1.4526 (3)	0.64782 (8)	0.0215 (2)
H2A	0.5090	1.5594	0.6026	0.026*
C3	0.58198 (10)	1.4917 (3)	0.72954 (9)	0.0223 (3)
H3A	0.5447	1.6288	0.7405	0.027*
C4	0.65730 (10)	1.3329 (3)	0.79635 (8)	0.0220 (3)
H4A	0.6707	1.3618	0.8520	0.026*
C5	0.71206 (10)	1.1340 (3)	0.78079 (8)	0.0207 (2)
H5A	0.7626	1.0245	0.8259	0.025*
C6	0.69360 (9)	1.0923 (3)	0.69871 (7)	0.0170 (2)
C7	0.74892 (9)	0.8943 (2)	0.67830 (7)	0.0172 (2)
H7A	0.8000	0.7812	0.7219	0.021*
C8	0.73070 (9)	0.8631 (2)	0.59846 (7)	0.0157 (2)
C9	0.64806 (9)	1.0288 (3)	0.53044 (7)	0.0175 (2)
C10	0.79048 (9)	0.6641 (2)	0.57920 (7)	0.0159 (2)
C11	0.77572 (10)	0.6015 (3)	0.50172 (7)	0.0188 (2)
H11A	0.7242	0.6834	0.4503	0.023*
C12	0.91583 (9)	0.3476 (2)	0.61957 (7)	0.0167 (2)
C13	1.04154 (10)	−0.0065 (3)	0.63373 (8)	0.0228 (3)
H13A	1.0934	−0.1250	0.6785	0.034*
H13B	1.0773	0.0999	0.6101	0.034*
H13C	0.9854	−0.1171	0.5891	0.034*
H1N2	1.0201 (16)	0.177 (4)	0.7226 (13)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01899 (15)	0.02255 (16)	0.01429 (14)	0.00258 (11)	0.00693 (11)	−0.00217 (10)
O1	0.0194 (4)	0.0245 (4)	0.0164 (4)	0.0064 (3)	0.0087 (3)	0.0043 (3)
O2	0.0213 (4)	0.0301 (5)	0.0154 (4)	0.0051 (4)	0.0085 (3)	0.0045 (4)
N1	0.0147 (4)	0.0188 (5)	0.0143 (4)	0.0008 (4)	0.0056 (4)	0.0000 (4)
N2	0.0185 (5)	0.0242 (5)	0.0156 (5)	0.0060 (4)	0.0054 (4)	−0.0004 (4)
C1	0.0162 (5)	0.0193 (5)	0.0171 (5)	−0.0007 (4)	0.0087 (4)	0.0005 (4)
C2	0.0183 (5)	0.0208 (6)	0.0254 (6)	0.0035 (5)	0.0110 (5)	0.0022 (5)
C3	0.0199 (6)	0.0215 (6)	0.0296 (6)	−0.0006 (5)	0.0155 (5)	−0.0035 (5)
C4	0.0196 (6)	0.0268 (6)	0.0212 (6)	−0.0020 (5)	0.0114 (5)	−0.0054 (5)
C5	0.0168 (5)	0.0266 (6)	0.0172 (5)	0.0008 (5)	0.0075 (4)	−0.0012 (5)
C6	0.0136 (5)	0.0193 (5)	0.0171 (5)	−0.0009 (4)	0.0070 (4)	−0.0010 (4)
C7	0.0148 (5)	0.0197 (5)	0.0149 (5)	0.0019 (4)	0.0058 (4)	0.0007 (4)
C8	0.0137 (5)	0.0168 (5)	0.0154 (5)	−0.0001 (4)	0.0064 (4)	0.0011 (4)
C9	0.0151 (5)	0.0196 (5)	0.0177 (5)	0.0008 (4)	0.0082 (4)	0.0017 (4)
C10	0.0138 (5)	0.0173 (5)	0.0149 (5)	−0.0002 (4)	0.0061 (4)	0.0001 (4)
C11	0.0181 (5)	0.0208 (6)	0.0154 (5)	0.0029 (4)	0.0068 (4)	0.0000 (4)
C12	0.0145 (5)	0.0183 (5)	0.0151 (5)	−0.0017 (4)	0.0058 (4)	−0.0014 (4)
C13	0.0191 (5)	0.0237 (6)	0.0235 (6)	0.0037 (5)	0.0092 (5)	−0.0028 (5)

S1—C11	1.7265 (13)	C3—H3A	0.9500
S1—C12	1.7517 (12)	C4—C5	1.3807 (17)
O1—C1	1.3757 (14)	C4—H4A	0.9500
O1—C9	1.3781 (15)	C5—C6	1.4054 (16)
O2—C9	1.2094 (15)	C5—H5A	0.9500
N1—C12	1.3129 (15)	C6—C7	1.4296 (16)
N1—C10	1.3971 (15)	C7—C8	1.3598 (16)
N2—C12	1.3457 (16)	C7—H7A	0.9500
N2—C13	1.4482 (16)	C8—C10	1.4674 (16)
N2—H1N2	0.87 (2)	C8—C9	1.4683 (16)
C1—C2	1.3903 (17)	C10—C11	1.3621 (16)
C1—C6	1.3923 (16)	C11—H11A	0.9500
C2—C3	1.3838 (18)	C13—H13A	0.9800
C2—H2A	0.9500	C13—H13B	0.9800
C3—C4	1.4001 (19)	C13—H13C	0.9800
C11—S1—C12	89.04 (6)	C8—C7—C6	122.02 (11)
C1—O1—C9	123.10 (9)	C8—C7—H7A	119.0
C12—N1—C10	110.22 (10)	C6—C7—H7A	119.0
C12—N2—C13	122.07 (11)	C7—C8—C10	121.21 (10)
C12—N2—H1N2	118.6 (13)	C7—C8—C9	118.93 (11)
C13—N2—H1N2	119.3 (13)	C10—C8—C9	119.84 (10)
O1—C1—C2	117.51 (11)	O2—C9—O1	116.01 (11)
O1—C1—C6	120.24 (11)	O2—C9—C8	126.56 (11)
C2—C1—C6	122.25 (11)	O1—C9—C8	117.43 (10)
C3—C2—C1	118.10 (12)	C11—C10—N1	115.57 (11)
C3—C2—H2A	121.0	C11—C10—C8	127.05 (11)
C1—C2—H2A	121.0	N1—C10—C8	117.38 (10)
C2—C3—C4	121.28 (12)	C10—C11—S1	110.40 (9)
C2—C3—H3A	119.4	C10—C11—H11A	124.8
C4—C3—H3A	119.4	S1—C11—H11A	124.8
C5—C4—C3	119.60 (12)	N1—C12—N2	125.28 (11)
C5—C4—H4A	120.2	N1—C12—S1	114.75 (9)
C3—C4—H4A	120.2	N2—C12—S1	119.97 (9)
C4—C5—C6	120.49 (12)	N2—C13—H13A	109.5
C4—C5—H5A	119.8	N2—C13—H13B	109.5
C6—C5—H5A	119.8	H13A—C13—H13B	109.5
C1—C6—C5	118.27 (11)	N2—C13—H13C	109.5
C1—C6—C7	118.21 (11)	H13A—C13—H13C	109.5
C5—C6—C7	123.52 (11)	H13B—C13—H13C	109.5
C9—O1—C1—C2	178.87 (11)	C7—C8—C9—O2	−177.09 (12)
C9—O1—C1—C6	−0.99 (17)	C10—C8—C9—O2	1.73 (19)
O1—C1—C2—C3	−179.64 (11)	C7—C8—C9—O1	2.65 (16)
C6—C1—C2—C3	0.21 (19)	C10—C8—C9—O1	−178.53 (10)
C1—C2—C3—C4	−0.76 (19)	C12—N1—C10—C11	−1.08 (15)
C2—C3—C4—C5	0.3 (2)	C12—N1—C10—C8	178.73 (10)
C3—C4—C5—C6	0.75 (19)	C7—C8—C10—C11	175.76 (12)
O1—C1—C6—C5	−179.36 (11)	C9—C8—C10—C11	−3.03 (19)
C2—C1—C6—C5	0.79 (18)	C7—C8—C10—N1	−4.03 (17)
O1—C1—C6—C7	0.75 (17)	C9—C8—C10—N1	177.18 (10)
C2—C1—C6—C7	−179.10 (11)	N1—C10—C11—S1	0.53 (14)
C4—C5—C6—C1	−1.27 (18)	C8—C10—C11—S1	−179.26 (10)
C4—C5—C6—C7	178.62 (12)	C12—S1—C11—C10	0.09 (10)
C1—C6—C7—C8	1.30 (18)	C10—N1—C12—N2	−178.77 (12)
C5—C6—C7—C8	−178.59 (12)	C10—N1—C12—S1	1.14 (13)
C6—C7—C8—C10	178.23 (11)	C13—N2—C12—N1	−178.67 (12)
C6—C7—C8—C9	−2.98 (18)	C13—N2—C12—S1	1.43 (17)
C1—O1—C9—O2	179.07 (11)	C11—S1—C12—N1	−0.74 (10)
C1—O1—C9—C8	−0.70 (16)	C11—S1—C12—N2	179.17 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.87 (2)	2.24 (2)	3.0331 (15)	152 (2)
C4—H4A···O2ii	0.95	2.44	3.3247 (16)	154
C13—H13C···Cg1iii	0.98	2.70	3.5026 (16)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/N1/C10–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.87 (2)	2.24 (2)	3.0331 (15)	152 (2)
C4—H4A⋯O2ii	0.95	2.44	3.3247 (16)	154
C13—H13C⋯Cg1iii	0.98	2.70	3.5026 (16)	139

Symmetry codes: (i) ; (ii) ; (iii) .