(Z)-3-(2-{2-[1-(4-Hy-droxy-phen-yl)ethyl-idene]hydrazin-1-yl}-1,3-thia-zol-4-yl)-2H-chromen-2-one.

In the title compound, C(20)H(15)N(3)O(3)S, an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The chromene ring system is inclined at dihedral angles of 14.21 (9) and 9.91 (10)°, respectively, with respect to the thia-zole and benzene rings. The thia-zole ring makes a dihedral angle of 24.06 (11)° with the benzene ring. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules into a zigzag chain along [20]. Weak N-H⋯O and C-H⋯O inter-actions connect the chains into a three-dimensional network. π-π stacking inter-actions with a centroid-centroid distance of 3.4209 (14) Å are also observed between the chains.

Related literature

For a related structure, see: Arshad et al. (2010 ▶). For the synthesis, see: Siddiqui et al. (2009 ▶); Liu et al. (2008 ▶). For general background to and the biological activity of coumarin derivatives, see: Anderson et al. (2002 ▶); Finn et al. (2004 ▶); Hofmanova et al. (1998 ▶). For the biological activity of amino­thia­zole derivatives, see: Hiremath et al. (1992 ▶); Gursoy & Karah (2000 ▶); Jayashree et al. (2005 ▶); Patt et al. (1992 ▶). For bond-length data, see: Allen et al. (1987 ▶). 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

C20H15N3O3S

M = 377.41

Monoclinic,

a = 9.1117 (16) Å

b = 16.225 (3) Å

c = 12.113 (2) Å

β = 104.657 (3)°

V = 1732.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.38 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.922, T max = 0.990

16535 measured reflections

3957 independent reflections

2932 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.161

S = 1.10

3957 reflections

253 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.41 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/S1600536810021604/is2557sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021604/is2557Isup2.hkl

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

C20H15N3O3S	F(000) = 784
Mr = 377.41	Dx = 1.447 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2347 reflections
a = 9.1117 (16) Å	θ = 2.8–27.3°
b = 16.225 (3) Å	µ = 0.21 mm−1
c = 12.113 (2) Å	T = 100 K
β = 104.657 (3)°	Needle, yellow
V = 1732.5 (5) Å3	0.38 × 0.06 × 0.05 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	3957 independent reflections
Radiation source: fine-focus sealed tube	2932 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.922, Tmax = 0.990	k = −21→21
16535 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0927P)2] where P = (Fo2 + 2Fc2)/3
3957 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.41 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 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	0.38934 (7)	0.12646 (3)	0.08727 (5)	0.01862 (18)
O1	−0.03963 (18)	−0.12925 (9)	0.20648 (14)	0.0161 (4)
O2	0.05580 (19)	−0.00659 (10)	0.25771 (15)	0.0200 (4)
O3	0.8063 (2)	0.48865 (10)	−0.15666 (16)	0.0223 (4)
N1	0.2563 (2)	−0.00002 (11)	−0.02742 (17)	0.0157 (4)
N2	0.4034 (2)	0.07847 (12)	−0.12284 (19)	0.0180 (4)
N3	0.4819 (2)	0.15129 (11)	−0.11761 (17)	0.0153 (4)
C1	0.0479 (3)	−0.06337 (13)	0.1917 (2)	0.0155 (5)
C2	−0.0638 (2)	−0.19722 (13)	0.1346 (2)	0.0148 (5)
C3	−0.1574 (3)	−0.25933 (14)	0.1574 (2)	0.0181 (5)
H3A	−0.2042	−0.2544	0.2170	0.022*
C4	−0.1785 (3)	−0.32860 (14)	0.0888 (2)	0.0198 (5)
H4A	−0.2406	−0.3708	0.1025	0.024*
C5	−0.1085 (3)	−0.33653 (14)	−0.0009 (2)	0.0212 (5)
H5A	−0.1237	−0.3838	−0.0458	0.025*
C6	−0.0166 (3)	−0.27378 (14)	−0.0225 (2)	0.0190 (5)
H6A	0.0295	−0.2789	−0.0825	0.023*
C7	0.0075 (2)	−0.20265 (13)	0.0454 (2)	0.0152 (5)
C8	0.1015 (3)	−0.13536 (13)	0.0300 (2)	0.0147 (5)
H8A	0.1499	−0.1381	−0.0289	0.018*
C9	0.1230 (2)	−0.06783 (13)	0.0976 (2)	0.0146 (5)
C10	0.2180 (2)	0.00109 (13)	0.07732 (19)	0.0138 (5)
C11	0.2764 (3)	0.06418 (14)	0.1475 (2)	0.0194 (5)
H11A	0.2582	0.0730	0.2188	0.023*
C12	0.3457 (2)	0.06236 (13)	−0.0311 (2)	0.0151 (5)
C13	0.5341 (3)	0.17206 (13)	−0.2030 (2)	0.0160 (5)
C14	0.6101 (2)	0.25398 (13)	−0.1918 (2)	0.0150 (5)
C15	0.5766 (3)	0.31265 (14)	−0.1168 (2)	0.0184 (5)
H15A	0.5077	0.2996	−0.0745	0.022*
C16	0.6444 (3)	0.38995 (14)	−0.1045 (2)	0.0207 (5)
H16A	0.6213	0.4280	−0.0541	0.025*
C17	0.7469 (3)	0.41031 (13)	−0.1679 (2)	0.0177 (5)
C18	0.7836 (3)	0.35256 (13)	−0.2415 (2)	0.0159 (5)
H18A	0.8541	0.3655	−0.2826	0.019*
C19	0.7150 (3)	0.27562 (13)	−0.2536 (2)	0.0166 (5)
H19A	0.7392	0.2377	−0.3038	0.020*
C20	0.5172 (3)	0.12174 (14)	−0.3094 (2)	0.0208 (5)
H20A	0.4122	0.1084	−0.3403	0.031*
H20B	0.5749	0.0718	−0.2914	0.031*
H20C	0.5537	0.1528	−0.3644	0.031*
H12N	0.364 (3)	0.0512 (15)	−0.186 (2)	0.016 (7)*
H13O	0.894 (4)	0.491 (2)	−0.176 (3)	0.060 (11)*

	U11	U22	U33	U12	U13	U23
S1	0.0201 (3)	0.0173 (3)	0.0188 (3)	−0.0056 (2)	0.0057 (3)	−0.0023 (2)
O1	0.0168 (8)	0.0155 (8)	0.0185 (9)	−0.0017 (6)	0.0093 (7)	−0.0006 (6)
O2	0.0204 (9)	0.0213 (8)	0.0198 (9)	−0.0021 (6)	0.0081 (8)	−0.0047 (7)
O3	0.0233 (10)	0.0163 (8)	0.0321 (11)	−0.0043 (7)	0.0162 (9)	−0.0022 (7)
N1	0.0157 (10)	0.0157 (9)	0.0173 (11)	−0.0020 (7)	0.0070 (9)	0.0005 (7)
N2	0.0210 (11)	0.0158 (9)	0.0193 (12)	−0.0052 (8)	0.0089 (9)	−0.0005 (8)
N3	0.0126 (9)	0.0149 (9)	0.0176 (11)	−0.0022 (7)	0.0023 (8)	0.0020 (7)
C1	0.0134 (11)	0.0169 (10)	0.0156 (12)	0.0005 (8)	0.0024 (9)	0.0012 (9)
C2	0.0131 (11)	0.0149 (10)	0.0152 (12)	0.0017 (8)	0.0016 (9)	0.0007 (8)
C3	0.0165 (11)	0.0222 (11)	0.0162 (12)	0.0000 (9)	0.0053 (10)	0.0032 (9)
C4	0.0169 (12)	0.0190 (11)	0.0236 (14)	−0.0052 (9)	0.0050 (10)	0.0024 (9)
C5	0.0224 (13)	0.0186 (11)	0.0213 (14)	−0.0040 (9)	0.0033 (11)	−0.0030 (10)
C6	0.0200 (12)	0.0212 (11)	0.0162 (13)	−0.0018 (9)	0.0055 (10)	−0.0020 (9)
C7	0.0141 (11)	0.0162 (10)	0.0143 (12)	0.0013 (8)	0.0017 (9)	0.0010 (8)
C8	0.0144 (11)	0.0188 (11)	0.0114 (12)	0.0017 (8)	0.0041 (9)	0.0018 (8)
C9	0.0122 (11)	0.0164 (10)	0.0161 (12)	0.0010 (8)	0.0054 (9)	0.0020 (9)
C10	0.0109 (11)	0.0170 (10)	0.0127 (12)	0.0016 (8)	0.0018 (9)	0.0028 (8)
C11	0.0227 (12)	0.0187 (11)	0.0194 (13)	−0.0024 (9)	0.0100 (11)	0.0000 (9)
C12	0.0129 (11)	0.0161 (10)	0.0159 (12)	0.0014 (8)	0.0029 (9)	0.0017 (9)
C13	0.0129 (11)	0.0174 (11)	0.0178 (13)	0.0009 (8)	0.0041 (10)	0.0027 (9)
C14	0.0127 (11)	0.0179 (11)	0.0140 (12)	0.0011 (8)	0.0027 (9)	0.0037 (9)
C15	0.0174 (12)	0.0202 (11)	0.0207 (13)	−0.0025 (9)	0.0106 (10)	0.0015 (9)
C16	0.0243 (13)	0.0168 (11)	0.0246 (14)	−0.0010 (9)	0.0127 (12)	−0.0037 (9)
C17	0.0183 (12)	0.0125 (10)	0.0233 (14)	−0.0009 (8)	0.0073 (10)	0.0027 (9)
C18	0.0139 (11)	0.0193 (11)	0.0162 (12)	0.0004 (8)	0.0067 (10)	0.0028 (9)
C19	0.0166 (11)	0.0188 (11)	0.0149 (12)	0.0033 (8)	0.0049 (10)	0.0015 (9)
C20	0.0208 (12)	0.0223 (12)	0.0198 (13)	−0.0039 (9)	0.0061 (11)	−0.0015 (10)

S1—C11	1.730 (2)	C6—H6A	0.9300
S1—C12	1.735 (2)	C7—C8	1.429 (3)
O1—C1	1.372 (3)	C8—C9	1.352 (3)
O1—C2	1.388 (3)	C8—H8A	0.9300
O2—C1	1.210 (3)	C9—C10	1.472 (3)
O3—C17	1.375 (3)	C10—C11	1.351 (3)
O3—H13O	0.89 (4)	C11—H11A	0.9300
N1—C12	1.307 (3)	C13—C14	1.489 (3)
N1—C10	1.399 (3)	C13—C20	1.500 (3)
N2—C12	1.369 (3)	C14—C19	1.400 (3)
N2—N3	1.374 (3)	C14—C15	1.401 (3)
N2—H12N	0.88 (3)	C15—C16	1.389 (3)
N3—C13	1.288 (3)	C15—H15A	0.9300
C1—C9	1.471 (3)	C16—C17	1.391 (3)
C2—C3	1.393 (3)	C16—H16A	0.9300
C2—C7	1.397 (3)	C17—C18	1.391 (3)
C3—C4	1.382 (3)	C18—C19	1.387 (3)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.397 (3)	C19—H19A	0.9300
C4—H4A	0.9300	C20—H20A	0.9600
C5—C6	1.385 (3)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600
C6—C7	1.402 (3)
C11—S1—C12	87.85 (11)	C11—C10—C9	128.6 (2)
C1—O1—C2	122.81 (18)	N1—C10—C9	115.73 (19)
C17—O3—H13O	112 (2)	C10—C11—S1	110.99 (18)
C12—N1—C10	108.79 (19)	C10—C11—H11A	124.5
C12—N2—N3	115.41 (19)	S1—C11—H11A	124.5
C12—N2—H12N	117.1 (17)	N1—C12—N2	123.1 (2)
N3—N2—H12N	124.5 (17)	N1—C12—S1	116.75 (18)
C13—N3—N2	118.8 (2)	N2—C12—S1	120.13 (17)
O2—C1—O1	116.5 (2)	N3—C13—C14	114.7 (2)
O2—C1—C9	126.0 (2)	N3—C13—C20	124.7 (2)
O1—C1—C9	117.55 (19)	C14—C13—C20	120.6 (2)
O1—C2—C3	117.3 (2)	C19—C14—C15	117.8 (2)
O1—C2—C7	120.29 (19)	C19—C14—C13	122.7 (2)
C3—C2—C7	122.4 (2)	C15—C14—C13	119.5 (2)
C4—C3—C2	117.9 (2)	C16—C15—C14	121.3 (2)
C4—C3—H3A	121.1	C16—C15—H15A	119.4
C2—C3—H3A	121.1	C14—C15—H15A	119.4
C3—C4—C5	121.4 (2)	C15—C16—C17	119.8 (2)
C3—C4—H4A	119.3	C15—C16—H16A	120.1
C5—C4—H4A	119.3	C17—C16—H16A	120.1
C6—C5—C4	119.7 (2)	O3—C17—C16	117.8 (2)
C6—C5—H5A	120.1	O3—C17—C18	122.3 (2)
C4—C5—H5A	120.1	C16—C17—C18	119.8 (2)
C5—C6—C7	120.5 (2)	C19—C18—C17	120.0 (2)
C5—C6—H6A	119.8	C19—C18—H18A	120.0
C7—C6—H6A	119.8	C17—C18—H18A	120.0
C2—C7—C6	118.1 (2)	C18—C19—C14	121.3 (2)
C2—C7—C8	117.6 (2)	C18—C19—H19A	119.4
C6—C7—C8	124.3 (2)	C14—C19—H19A	119.4
C9—C8—C7	122.7 (2)	C13—C20—H20A	109.5
C9—C8—H8A	118.7	C13—C20—H20B	109.5
C7—C8—H8A	118.7	H20A—C20—H20B	109.5
C8—C9—C1	119.0 (2)	C13—C20—H20C	109.5
C8—C9—C10	121.0 (2)	H20A—C20—H20C	109.5
C1—C9—C10	120.02 (19)	H20B—C20—H20C	109.5
C11—C10—N1	115.6 (2)
C12—N2—N3—C13	−177.2 (2)	C8—C9—C10—N1	12.9 (3)
C2—O1—C1—O2	177.4 (2)	C1—C9—C10—N1	−166.16 (19)
C2—O1—C1—C9	−2.4 (3)	N1—C10—C11—S1	−1.4 (3)
C1—O1—C2—C3	−178.8 (2)	C9—C10—C11—S1	176.69 (18)
C1—O1—C2—C7	2.9 (3)	C12—S1—C11—C10	0.95 (18)
O1—C2—C3—C4	−177.9 (2)	C10—N1—C12—N2	180.0 (2)
C7—C2—C3—C4	0.3 (4)	C10—N1—C12—S1	−0.4 (2)
C2—C3—C4—C5	0.0 (4)	N3—N2—C12—N1	173.3 (2)
C3—C4—C5—C6	−0.4 (4)	N3—N2—C12—S1	−6.3 (3)
C4—C5—C6—C7	0.4 (4)	C11—S1—C12—N1	−0.31 (19)
O1—C2—C7—C6	177.9 (2)	C11—S1—C12—N2	179.3 (2)
C3—C2—C7—C6	−0.3 (3)	N2—N3—C13—C14	176.85 (19)
O1—C2—C7—C8	−1.6 (3)	N2—N3—C13—C20	−0.7 (3)
C3—C2—C7—C8	−179.8 (2)	N3—C13—C14—C19	158.3 (2)
C5—C6—C7—C2	−0.1 (3)	C20—C13—C14—C19	−24.1 (3)
C5—C6—C7—C8	179.4 (2)	N3—C13—C14—C15	−21.8 (3)
C2—C7—C8—C9	−0.1 (3)	C20—C13—C14—C15	155.9 (2)
C6—C7—C8—C9	−179.6 (2)	C19—C14—C15—C16	0.4 (4)
C7—C8—C9—C1	0.5 (3)	C13—C14—C15—C16	−179.6 (2)
C7—C8—C9—C10	−178.6 (2)	C14—C15—C16—C17	0.4 (4)
O2—C1—C9—C8	−179.2 (2)	C15—C16—C17—O3	177.3 (2)
O1—C1—C9—C8	0.7 (3)	C15—C16—C17—C18	−1.4 (4)
O2—C1—C9—C10	−0.1 (4)	O3—C17—C18—C19	−177.0 (2)
O1—C1—C9—C10	179.81 (19)	C16—C17—C18—C19	1.6 (4)
C12—N1—C10—C11	1.2 (3)	C17—C18—C19—C14	−0.9 (4)
C12—N1—C10—C9	−177.19 (19)	C15—C14—C19—C18	−0.1 (3)
C8—C9—C10—C11	−165.2 (2)	C13—C14—C19—C18	179.8 (2)
C1—C9—C10—C11	15.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H12N···O3i	0.88 (2)	2.36 (2)	3.213 (3)	164 (2)
O3—H13O···O2ii	0.89 (4)	1.87 (4)	2.743 (3)	169 (3)
C5—H5A···O3iii	0.93	2.46	3.386 (3)	173
C11—H11A···O2	0.93	2.39	2.915 (3)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H12N⋯O3i	0.88 (2)	2.36 (2)	3.213 (3)	164 (2)
O3—H13O⋯O2ii	0.89 (4)	1.87 (4)	2.743 (3)	169 (3)
C5—H5A⋯O3iii	0.93	2.46	3.386 (3)	173
C11—H11A⋯O2	0.93	2.39	2.915 (3)	115

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