3-{2-[2-(2-Fluoro-benzyl-idene)hydrazin-yl]-1,3-thia-zol-4-yl}-2H-chromen-2-one.

In the title compound, C(19)H(12)FN(3)O(2)S, the chromene ring system and the thia-zole ring are approximately planar [maximum deviations of 0.023 (3) Å and 0.004 (2) Å, respectively]. The chromene ring system is inclined at angles of 4.78 (10) and 26.51 (10)° with respect to the thia-zole and benzene rings, respectively, while the thia-zole ring makes a dihedral angle of 23.07 (12)° with the benzene ring. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring motif. The crystal packing is consolidated by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into chains parallel to [100], and by C-H⋯π and π-π [centroid-centroid distance = 3.4954 (15) Å] stacking inter-actions.

Related literature

For the synthesis of the title compound, see: Lv et al. (2010 ▶); Siddiqui et al. (2009 ▶). For general background to and the biological activity of coumarin derivatives, see: Anderson et al. (2002 ▶); Tassies et al. (2002 ▶); Mitscher (2002 ▶); Lafitte et al. (2002 ▶); Moffett (1964 ▶); Weber et al. (1998 ▶). For the biological activity of amino­thia­zoles derivatives, see: Hiremath et al. (1992 ▶); Habib & Khalil (1984 ▶); Karah et al. (1998 ▶); Gursoy & Karah (2000 ▶); Lednicer et al. (1990 ▶); Kim et al. (2002 ▶); Wattenberg et al. (1979 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H12FN3O2S

M = 365.38

Orthorhombic,

a = 12.303 (2) Å

b = 10.4477 (17) Å

c = 25.247 (4) Å

V = 3245.2 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.37 × 0.08 × 0.04 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.919, T max = 0.991

13589 measured reflections

2855 independent reflections

1971 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.04

2855 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.33 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 datablocks global, I. DOI: 10.1107/S1600536810018647/tk2674sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018647/tk2674Isup2.hkl

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

C19H12FN3O2S	F(000) = 1504
Mr = 365.38	Dx = 1.496 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1466 reflections
a = 12.303 (2) Å	θ = 3.2–27.1°
b = 10.4477 (17) Å	µ = 0.23 mm−1
c = 25.247 (4) Å	T = 100 K
V = 3245.2 (9) Å3	Needle, yellow
Z = 8	0.37 × 0.08 × 0.04 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	2855 independent reflections
Radiation source: fine-focus sealed tube	1971 reflections with I > 2σ(I)
graphite	Rint = 0.082
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→14
Tmin = 0.919, Tmax = 0.991	k = −12→12
13589 measured reflections	l = −25→30

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.4898P] where P = (Fo2 + 2Fc2)/3
2855 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.88953 (5)	0.06999 (6)	0.02651 (3)	0.02149 (19)
F1	0.54027 (12)	−0.24735 (15)	0.18957 (7)	0.0376 (5)
O1	0.85525 (13)	0.52077 (17)	−0.12371 (7)	0.0230 (5)
O2	0.97044 (14)	0.41533 (18)	−0.07423 (8)	0.0309 (5)
N1	0.72862 (17)	−0.0844 (2)	0.07751 (9)	0.0205 (5)
N2	0.68221 (19)	0.0019 (2)	0.04366 (9)	0.0211 (5)
N3	0.71706 (16)	0.17627 (19)	−0.01285 (9)	0.0179 (5)
C1	0.8140 (2)	−0.2887 (2)	0.14056 (11)	0.0225 (6)
H1	0.8600	−0.2571	0.1144	0.027*
C2	0.8520 (2)	−0.3806 (2)	0.17528 (11)	0.0244 (7)
H2	0.9232	−0.4097	0.1725	0.029*
C3	0.7845 (2)	−0.4299 (3)	0.21429 (11)	0.0293 (7)
H3	0.8099	−0.4933	0.2370	0.035*
C4	0.6792 (2)	−0.3843 (3)	0.21930 (11)	0.0296 (7)
H4	0.6334	−0.4155	0.2456	0.035*
C5	0.6442 (2)	−0.2922 (3)	0.18451 (12)	0.0258 (7)
C6	0.7077 (2)	−0.2424 (2)	0.14401 (11)	0.0214 (6)
C7	0.6640 (2)	−0.1475 (2)	0.10749 (11)	0.0210 (6)
H7	0.5895	−0.1329	0.1060	0.025*
C8	0.7499 (2)	0.0851 (2)	0.01854 (10)	0.0181 (6)
C9	0.9051 (2)	0.1990 (2)	−0.01532 (11)	0.0216 (6)
H9	0.9717	0.2340	−0.0250	0.026*
C10	0.80743 (19)	0.2424 (2)	−0.03219 (10)	0.0169 (6)
C11	0.78532 (19)	0.3487 (2)	−0.06865 (11)	0.0176 (6)
C12	0.6839 (2)	0.3765 (2)	−0.08582 (10)	0.0181 (6)
H12	0.6256	0.3283	−0.0735	0.022*
C13	0.6639 (2)	0.4783 (2)	−0.12245 (11)	0.0197 (6)
C14	0.5599 (2)	0.5110 (3)	−0.14162 (11)	0.0225 (6)
H14	0.4993	0.4657	−0.1300	0.027*
C15	0.5474 (2)	0.6092 (2)	−0.17731 (11)	0.0244 (7)
H15	0.4785	0.6302	−0.1897	0.029*
C16	0.6378 (2)	0.6774 (3)	−0.19495 (11)	0.0264 (7)
H16	0.6288	0.7433	−0.2193	0.032*
C17	0.7405 (2)	0.6480 (2)	−0.17669 (11)	0.0243 (7)
H17	0.8008	0.6940	−0.1881	0.029*
C18	0.7515 (2)	0.5489 (2)	−0.14105 (11)	0.0197 (6)
C19	0.8764 (2)	0.4266 (2)	−0.08730 (11)	0.0206 (6)
H12N	0.615 (2)	0.019 (3)	0.0458 (11)	0.030 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0159 (3)	0.0227 (4)	0.0259 (4)	0.0030 (3)	−0.0001 (3)	0.0013 (3)
F1	0.0327 (10)	0.0392 (10)	0.0409 (12)	−0.0040 (8)	0.0141 (8)	0.0027 (9)
O1	0.0179 (10)	0.0250 (10)	0.0261 (12)	−0.0044 (8)	0.0005 (8)	0.0017 (9)
O2	0.0147 (10)	0.0368 (11)	0.0413 (14)	−0.0049 (9)	−0.0028 (9)	0.0075 (10)
N1	0.0232 (12)	0.0150 (11)	0.0233 (14)	0.0024 (10)	0.0011 (10)	−0.0016 (10)
N2	0.0160 (12)	0.0197 (12)	0.0277 (15)	0.0023 (11)	0.0025 (10)	0.0032 (11)
N3	0.0142 (11)	0.0176 (11)	0.0219 (14)	0.0009 (9)	0.0013 (9)	0.0004 (10)
C1	0.0245 (15)	0.0192 (13)	0.0237 (17)	−0.0059 (12)	0.0010 (12)	−0.0045 (13)
C2	0.0299 (16)	0.0183 (14)	0.0251 (18)	−0.0026 (12)	−0.0030 (13)	−0.0016 (13)
C3	0.0457 (19)	0.0181 (14)	0.0240 (18)	−0.0078 (14)	−0.0051 (13)	0.0032 (14)
C4	0.0436 (19)	0.0239 (15)	0.0212 (18)	−0.0147 (14)	0.0058 (14)	0.0001 (13)
C5	0.0262 (16)	0.0240 (15)	0.0273 (18)	−0.0067 (13)	0.0053 (13)	−0.0072 (14)
C6	0.0290 (15)	0.0144 (13)	0.0207 (17)	−0.0052 (12)	0.0006 (12)	−0.0050 (12)
C7	0.0242 (15)	0.0159 (13)	0.0228 (17)	−0.0007 (12)	0.0038 (12)	−0.0051 (12)
C8	0.0171 (13)	0.0158 (12)	0.0213 (16)	0.0024 (11)	−0.0012 (11)	−0.0051 (12)
C9	0.0170 (14)	0.0227 (14)	0.0252 (17)	0.0010 (12)	0.0042 (12)	−0.0024 (12)
C10	0.0148 (13)	0.0177 (12)	0.0183 (15)	−0.0012 (11)	−0.0001 (11)	−0.0049 (12)
C11	0.0165 (14)	0.0175 (13)	0.0189 (16)	−0.0013 (11)	0.0017 (11)	−0.0044 (12)
C12	0.0153 (13)	0.0189 (13)	0.0202 (16)	−0.0009 (11)	0.0040 (11)	−0.0034 (12)
C13	0.0218 (15)	0.0182 (13)	0.0191 (16)	0.0009 (11)	0.0026 (11)	−0.0040 (12)
C14	0.0219 (15)	0.0242 (15)	0.0215 (17)	0.0026 (12)	0.0023 (12)	−0.0015 (13)
C15	0.0263 (16)	0.0250 (15)	0.0220 (18)	0.0087 (13)	−0.0023 (12)	−0.0016 (13)
C16	0.0399 (18)	0.0188 (14)	0.0206 (18)	0.0042 (13)	−0.0005 (13)	0.0003 (13)
C17	0.0310 (16)	0.0208 (14)	0.0210 (17)	−0.0051 (13)	0.0027 (13)	−0.0020 (13)
C18	0.0211 (14)	0.0175 (13)	0.0206 (16)	0.0002 (11)	0.0007 (12)	−0.0051 (12)
C19	0.0214 (15)	0.0183 (13)	0.0222 (16)	−0.0009 (12)	−0.0004 (11)	−0.0010 (13)

S1—C9	1.723 (3)	C5—C6	1.388 (4)
S1—C8	1.736 (2)	C6—C7	1.456 (4)
F1—C5	1.367 (3)	C7—H7	0.9300
O1—C19	1.372 (3)	C9—C10	1.354 (3)
O1—C18	1.381 (3)	C9—H9	0.9300
O2—C19	1.209 (3)	C10—C11	1.469 (4)
N1—C7	1.281 (3)	C11—C12	1.353 (3)
N1—N2	1.368 (3)	C11—C19	1.462 (4)
N2—C8	1.361 (3)	C12—C13	1.431 (4)
N2—H12N	0.85 (3)	C12—H12	0.9300
N3—C8	1.303 (3)	C13—C18	1.387 (4)
N3—C10	1.397 (3)	C13—C14	1.410 (4)
C1—C2	1.382 (4)	C14—C15	1.374 (4)
C1—C6	1.397 (4)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.394 (4)
C2—C3	1.387 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.379 (4)
C3—C4	1.386 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.379 (4)
C4—C5	1.372 (4)	C17—H17	0.9300
C4—H4	0.9300
C9—S1—C8	88.17 (12)	C10—C9—H9	124.6
C19—O1—C18	122.7 (2)	S1—C9—H9	124.6
C7—N1—N2	116.7 (2)	C9—C10—N3	115.5 (2)
C8—N2—N1	117.2 (2)	C9—C10—C11	128.0 (2)
C8—N2—H12N	119.4 (19)	N3—C10—C11	116.5 (2)
N1—N2—H12N	121 (2)	C12—C11—C19	119.0 (2)
C8—N3—C10	109.1 (2)	C12—C11—C10	122.3 (2)
C2—C1—C6	121.2 (3)	C19—C11—C10	118.7 (2)
C2—C1—H1	119.4	C11—C12—C13	121.7 (2)
C6—C1—H1	119.4	C11—C12—H12	119.2
C1—C2—C3	120.4 (3)	C13—C12—H12	119.2
C1—C2—H2	119.8	C18—C13—C14	117.4 (2)
C3—C2—H2	119.8	C18—C13—C12	118.7 (2)
C4—C3—C2	119.8 (3)	C14—C13—C12	123.9 (2)
C4—C3—H3	120.1	C15—C14—C13	120.5 (2)
C2—C3—H3	120.1	C15—C14—H14	119.8
C5—C4—C3	118.4 (3)	C13—C14—H14	119.8
C5—C4—H4	120.8	C14—C15—C16	120.1 (2)
C3—C4—H4	120.8	C14—C15—H15	120.0
F1—C5—C4	118.3 (2)	C16—C15—H15	120.0
F1—C5—C6	117.8 (3)	C17—C16—C15	120.7 (3)
C4—C5—C6	123.9 (3)	C17—C16—H16	119.6
C5—C6—C1	116.3 (3)	C15—C16—H16	119.6
C5—C6—C7	120.9 (2)	C16—C17—C18	118.4 (3)
C1—C6—C7	122.8 (3)	C16—C17—H17	120.8
N1—C7—C6	119.7 (2)	C18—C17—H17	120.8
N1—C7—H7	120.2	C17—C18—O1	117.2 (2)
C6—C7—H7	120.2	C17—C18—C13	122.9 (2)
N3—C8—N2	124.1 (2)	O1—C18—C13	119.8 (2)
N3—C8—S1	116.36 (19)	O2—C19—O1	115.7 (2)
N2—C8—S1	119.6 (2)	O2—C19—C11	126.3 (2)
C10—C9—S1	110.85 (19)	O1—C19—C11	118.0 (2)
C7—N1—N2—C8	168.7 (2)	N3—C10—C11—C12	−4.5 (4)
C6—C1—C2—C3	0.5 (4)	C9—C10—C11—C19	−4.9 (4)
C1—C2—C3—C4	−1.6 (4)	N3—C10—C11—C19	176.0 (2)
C2—C3—C4—C5	1.0 (4)	C19—C11—C12—C13	1.2 (4)
C3—C4—C5—F1	−179.9 (2)	C10—C11—C12—C13	−178.3 (2)
C3—C4—C5—C6	0.7 (4)	C11—C12—C13—C18	0.7 (4)
F1—C5—C6—C1	178.9 (2)	C11—C12—C13—C14	179.9 (2)
C4—C5—C6—C1	−1.7 (4)	C18—C13—C14—C15	0.0 (4)
F1—C5—C6—C7	−1.3 (4)	C12—C13—C14—C15	−179.2 (3)
C4—C5—C6—C7	178.1 (2)	C13—C14—C15—C16	0.1 (4)
C2—C1—C6—C5	1.0 (4)	C14—C15—C16—C17	−0.5 (4)
C2—C1—C6—C7	−178.7 (2)	C15—C16—C17—C18	0.7 (4)
N2—N1—C7—C6	179.2 (2)	C16—C17—C18—O1	179.5 (2)
C5—C6—C7—N1	166.1 (2)	C16—C17—C18—C13	−0.6 (4)
C1—C6—C7—N1	−14.2 (4)	C19—O1—C18—C17	178.3 (2)
C10—N3—C8—N2	−179.4 (2)	C19—O1—C18—C13	−1.6 (4)
C10—N3—C8—S1	−0.9 (3)	C14—C13—C18—C17	0.3 (4)
N1—N2—C8—N3	−176.7 (2)	C12—C13—C18—C17	179.5 (2)
N1—N2—C8—S1	4.9 (3)	C14—C13—C18—O1	−179.8 (2)
C9—S1—C8—N3	0.9 (2)	C12—C13—C18—O1	−0.6 (4)
C9—S1—C8—N2	179.4 (2)	C18—O1—C19—O2	−177.4 (2)
C8—S1—C9—C10	−0.5 (2)	C18—O1—C19—C11	3.5 (3)
S1—C9—C10—N3	0.1 (3)	C12—C11—C19—O2	177.7 (3)
S1—C9—C10—C11	−179.0 (2)	C10—C11—C19—O2	−2.7 (4)
C8—N3—C10—C9	0.5 (3)	C12—C11—C19—O1	−3.3 (4)
C8—N3—C10—C11	179.7 (2)	C10—C11—C19—O1	176.3 (2)
C9—C10—C11—C12	174.6 (3)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	0.93	2.27	2.823 (3)	118
N2—H12N···O2i	0.85 (3)	2.04 (3)	2.852 (3)	161 (3)
C4—H4···Cg1ii	0.93	2.96	3.701 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2	0.93	2.27	2.823 (3)	118
N2—H12N⋯O2i	0.85 (3)	2.04 (3)	2.852 (3)	161 (3)
C4—H4⋯Cg1ii	0.93	2.96	3.701 (3)	138

Symmetry codes: (i) ; (ii) .