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

In the title compound, C(20)H(15)N(3)O(3)S, the thia-zole ring is approximately planar, with a maximum deviation of 0.003 (1) Å, and makes dihedral angles of 7.44 (6) and 1.88 (6)° with the hy-droxy-substituted phenyl ring and the pyran ring, respectively. The hydroxyl group is disordered over two sets of sites, with an occupancy ratio of 0.567 (3):0.433 (3). In the crystal, the major disorder component mol-ecules are connected via bifurcated (three-centre) O-H⋯O and C-H⋯O hydrogen bonds, generating R(1) (2)(6) motifs and resulting in supra-molecular chains along the a axis. In the minor occupancy component, however, mol-ecules are connected via C-H⋯O hydrogen bonds, forming supra-molecular chains along the b axis. Furthermore, the crystal structure is stabilized by π-π inter-actions between the thia-zole rings [centroid-centroid distance = 3.5476 (7) Å].

Related literature

For details of coumarin derivatives, see: Raghu et al. (2009 ▶); Gursoy & Karali (2003 ▶); Chimenti et al. (2010 ▶); Kamal et al. (2009 ▶); Kalkhambkar et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For the synthesis of (E)-2-(1-(3-hy­droxy­phen­yl)ethyl­idene)hydrazinecarbothio­amide, see: Greenbaum et al. (2004 ▶) and for that of 3-[ω-bromo­acetyl coumarin, see: Nadeem et al. (2009 ▶).

Experimental

Crystal data

C20H15N3O3S

M = 377.41

Monoclinic,

a = 9.1569 (1) Å

b = 9.9070 (2) Å

c = 18.7478 (3) Å

β = 92.040 (1)°

V = 1699.67 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.34 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.929, T max = 0.979

29914 measured reflections

5400 independent reflections

4641 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.07

5400 reflections

271 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.30 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/S1600536811012189/wn2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012189/wn2428Isup2.hkl

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

C20H15N3O3S	F(000) = 784
Mr = 377.41	Dx = 1.475 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9987 reflections
a = 9.1569 (1) Å	θ = 3.0–30.8°
b = 9.9070 (2) Å	µ = 0.22 mm−1
c = 18.7478 (3) Å	T = 100 K
β = 92.040 (1)°	Plate, yellow
V = 1699.67 (5) Å3	0.34 × 0.32 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5400 independent reflections
Radiation source: fine-focus sealed tube	4641 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 31.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→13
Tmin = 0.929, Tmax = 0.979	k = −13→14
29914 measured reflections	l = −27→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.8634P] where P = (Fo2 + 2Fc2)/3
5400 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.30 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
S1	0.17023 (3)	0.06980 (3)	0.402397 (16)	0.02037 (8)
O1	−0.19100 (10)	0.47170 (9)	0.56457 (5)	0.01965 (18)
O2	−0.14551 (11)	0.40120 (11)	0.45684 (5)	0.0273 (2)
O3	0.75724 (18)	−0.54395 (18)	0.31831 (9)	0.0234 (5)	0.567 (3)
H1OA	0.797 (4)	−0.556 (4)	0.362 (2)	0.040 (10)*	0.567 (3)
O3A	0.4193 (3)	−0.2752 (3)	0.18640 (12)	0.0273 (7)	0.433 (3)
H1OB	0.363 (5)	−0.216 (5)	0.196 (2)	0.028 (11)*	0.433 (3)
N1	0.15618 (11)	0.10211 (11)	0.53942 (6)	0.0183 (2)
N2	0.31472 (13)	−0.07177 (12)	0.50380 (6)	0.0227 (2)
N3	0.36764 (12)	−0.13166 (12)	0.44404 (6)	0.0202 (2)
C1	−0.00034 (13)	0.28351 (13)	0.62488 (7)	0.0184 (2)
H1A	0.0626	0.2198	0.6456	0.022*
C2	−0.07700 (13)	0.37365 (13)	0.67004 (7)	0.0184 (2)
C3	−0.06263 (14)	0.37246 (14)	0.74487 (7)	0.0228 (3)
H3A	−0.0011	0.3101	0.7677	0.027*
C4	−0.13980 (14)	0.46385 (14)	0.78482 (7)	0.0231 (3)
H4A	−0.1304	0.4625	0.8344	0.028*
C5	−0.23196 (14)	0.55839 (14)	0.75060 (7)	0.0214 (2)
H5A	−0.2831	0.6198	0.7778	0.026*
C6	−0.24800 (14)	0.56170 (13)	0.67707 (7)	0.0203 (2)
H6A	−0.3089	0.6248	0.6544	0.024*
C7	−0.17091 (13)	0.46850 (13)	0.63785 (6)	0.0175 (2)
C8	−0.11845 (13)	0.38669 (13)	0.52030 (7)	0.0187 (2)
C9	−0.01694 (13)	0.28851 (12)	0.55271 (6)	0.0167 (2)
C10	0.06365 (13)	0.19757 (12)	0.50645 (6)	0.0169 (2)
C11	0.05871 (14)	0.19493 (13)	0.43358 (7)	0.0194 (2)
C12	0.21703 (13)	0.03050 (13)	0.49064 (7)	0.0183 (2)
C13	0.45893 (13)	−0.23030 (13)	0.45086 (7)	0.0186 (2)
C14	0.50587 (13)	−0.28993 (12)	0.38266 (7)	0.0179 (2)
C15	0.43761 (13)	−0.25098 (13)	0.31754 (7)	0.0189 (2)
H15A	0.3632	−0.1871	0.3171	0.023*
C16	0.48063 (14)	−0.30725 (13)	0.25395 (7)	0.0210 (2)
H16A	0.4359	−0.2796	0.2111	0.025*	0.567 (3)
C17	0.58993 (15)	−0.40455 (14)	0.25351 (7)	0.0232 (3)
H17A	0.6179	−0.4426	0.2108	0.028*
C18	0.65664 (14)	−0.44400 (14)	0.31770 (8)	0.0232 (3)
H18A	0.7292	−0.5097	0.3178	0.028*	0.433 (3)
C19	0.61671 (14)	−0.38669 (13)	0.38209 (7)	0.0210 (2)
H19A	0.6639	−0.4129	0.4246	0.025*
C20	0.51371 (16)	−0.28472 (15)	0.52150 (7)	0.0262 (3)
H20A	0.5374	−0.2111	0.5531	0.039*
H20B	0.5995	−0.3383	0.5148	0.039*
H20C	0.4394	−0.3396	0.5418	0.039*
H1N2	0.338 (2)	−0.090 (2)	0.5468 (11)	0.038 (5)*
H11	0.0039 (18)	0.2534 (18)	0.4013 (9)	0.029 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.02210 (15)	0.02380 (16)	0.01531 (14)	0.00190 (11)	0.00199 (11)	−0.00074 (11)
O1	0.0222 (4)	0.0196 (4)	0.0170 (4)	0.0039 (3)	−0.0006 (3)	0.0017 (3)
O2	0.0337 (5)	0.0307 (5)	0.0174 (4)	0.0105 (4)	−0.0017 (4)	0.0032 (4)
O3	0.0226 (8)	0.0261 (9)	0.0213 (9)	0.0086 (6)	0.0010 (6)	−0.0031 (7)
O3A	0.0396 (14)	0.0249 (13)	0.0179 (11)	0.0025 (10)	0.0077 (9)	−0.0001 (9)
N1	0.0189 (5)	0.0191 (5)	0.0171 (5)	0.0013 (4)	0.0016 (4)	0.0008 (4)
N2	0.0244 (5)	0.0262 (6)	0.0176 (5)	0.0070 (4)	0.0024 (4)	0.0001 (4)
N3	0.0191 (5)	0.0224 (5)	0.0192 (5)	0.0025 (4)	0.0032 (4)	−0.0006 (4)
C1	0.0187 (5)	0.0186 (6)	0.0178 (5)	0.0025 (4)	−0.0005 (4)	0.0002 (4)
C2	0.0178 (5)	0.0197 (6)	0.0176 (5)	0.0012 (4)	−0.0006 (4)	−0.0014 (4)
C3	0.0225 (6)	0.0271 (7)	0.0186 (6)	0.0057 (5)	−0.0026 (5)	−0.0014 (5)
C4	0.0223 (6)	0.0289 (7)	0.0179 (6)	0.0029 (5)	−0.0013 (5)	−0.0045 (5)
C5	0.0193 (6)	0.0213 (6)	0.0236 (6)	0.0009 (5)	0.0018 (5)	−0.0048 (5)
C6	0.0186 (5)	0.0182 (6)	0.0240 (6)	0.0015 (4)	0.0000 (5)	−0.0001 (5)
C7	0.0178 (5)	0.0179 (5)	0.0167 (5)	−0.0012 (4)	−0.0004 (4)	0.0001 (4)
C8	0.0195 (5)	0.0176 (5)	0.0190 (6)	0.0007 (4)	0.0010 (4)	0.0011 (4)
C9	0.0167 (5)	0.0159 (5)	0.0174 (5)	−0.0003 (4)	0.0000 (4)	0.0005 (4)
C10	0.0172 (5)	0.0166 (5)	0.0169 (5)	−0.0009 (4)	0.0011 (4)	0.0010 (4)
C11	0.0219 (6)	0.0200 (6)	0.0164 (5)	0.0011 (4)	0.0003 (4)	0.0002 (4)
C12	0.0177 (5)	0.0199 (6)	0.0174 (5)	−0.0007 (4)	0.0014 (4)	0.0009 (4)
C13	0.0169 (5)	0.0194 (6)	0.0197 (6)	−0.0001 (4)	0.0015 (4)	0.0021 (4)
C14	0.0162 (5)	0.0175 (5)	0.0202 (6)	−0.0017 (4)	0.0019 (4)	0.0018 (4)
C15	0.0188 (5)	0.0167 (5)	0.0213 (6)	0.0005 (4)	0.0021 (4)	0.0028 (4)
C16	0.0240 (6)	0.0191 (6)	0.0201 (6)	−0.0022 (5)	0.0024 (5)	0.0026 (5)
C17	0.0266 (6)	0.0200 (6)	0.0234 (6)	−0.0014 (5)	0.0071 (5)	−0.0015 (5)
C18	0.0208 (6)	0.0192 (6)	0.0297 (7)	0.0026 (5)	0.0037 (5)	−0.0004 (5)
C19	0.0183 (5)	0.0204 (6)	0.0244 (6)	0.0011 (4)	0.0002 (5)	0.0016 (5)
C20	0.0286 (7)	0.0286 (7)	0.0213 (6)	0.0041 (5)	−0.0002 (5)	0.0043 (5)

S1—C11	1.7216 (13)	C5—C6	1.3815 (18)
S1—C12	1.7382 (13)	C5—H5A	0.9300
O1—C8	1.3706 (15)	C6—C7	1.3887 (17)
O1—C7	1.3799 (15)	C6—H6A	0.9300
O2—C8	1.2151 (15)	C8—C9	1.4626 (17)
O3—C18	1.352 (2)	C9—C10	1.4678 (17)
O3—H1OA	0.89 (4)	C10—C11	1.3655 (17)
O3A—C16	1.403 (3)	C11—H11	0.965 (17)
O3A—H1OB	0.80 (5)	C13—C14	1.4858 (17)
N1—C12	1.2987 (16)	C13—C20	1.4996 (18)
N1—C10	1.3990 (16)	C14—C19	1.3964 (17)
N2—C12	1.3682 (16)	C14—C15	1.4057 (17)
N2—N3	1.3713 (15)	C15—C16	1.3858 (18)
N2—H1N2	0.85 (2)	C15—H15A	0.9300
N3—C13	1.2894 (16)	C16—C17	1.3898 (18)
C1—C9	1.3570 (17)	C16—H16A	0.9300
C1—C2	1.4316 (17)	C17—C18	1.386 (2)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C7	1.3964 (17)	C18—C19	1.3946 (19)
C2—C3	1.4044 (17)	C18—H18A	0.9300
C3—C4	1.3849 (18)	C19—H19A	0.9300
C3—H3A	0.9300	C20—H20A	0.9600
C4—C5	1.4009 (19)	C20—H20B	0.9600
C4—H4A	0.9300	C20—H20C	0.9600
C11—S1—C12	88.13 (6)	C10—C11—S1	110.77 (10)
C8—O1—C7	122.58 (10)	C10—C11—H11	127.8 (10)
C18—O3—H1OA	111 (2)	S1—C11—H11	121.4 (10)
C16—O3A—H1OB	102 (3)	N1—C12—N2	124.87 (12)
C12—N1—C10	109.05 (10)	N1—C12—S1	116.77 (10)
C12—N2—N3	114.89 (11)	N2—C12—S1	118.36 (9)
C12—N2—H1N2	118.2 (13)	N3—C13—C14	114.99 (11)
N3—N2—H1N2	126.9 (13)	N3—C13—C20	123.73 (12)
C13—N3—N2	119.58 (11)	C14—C13—C20	121.27 (11)
C9—C1—C2	121.80 (11)	C19—C14—C15	118.86 (12)
C9—C1—H1A	119.1	C19—C14—C13	120.81 (11)
C2—C1—H1A	119.1	C15—C14—C13	120.33 (11)
C7—C2—C3	118.15 (11)	C16—C15—C14	120.36 (12)
C7—C2—C1	118.13 (11)	C16—C15—H15A	119.8
C3—C2—C1	123.71 (12)	C14—C15—H15A	119.8
C4—C3—C2	120.22 (12)	C15—C16—C17	120.73 (12)
C4—C3—H3A	119.9	C15—C16—O3A	124.63 (15)
C2—C3—H3A	119.9	C17—C16—O3A	114.63 (15)
C3—C4—C5	120.00 (12)	C15—C16—H16A	119.6
C3—C4—H4A	120.0	C17—C16—H16A	119.6
C5—C4—H4A	120.0	O3A—C16—H16A	5.1
C6—C5—C4	120.91 (12)	C18—C17—C16	119.04 (12)
C6—C5—H5A	119.5	C18—C17—H17A	120.5
C4—C5—H5A	119.5	C16—C17—H17A	120.5
C5—C6—C7	118.34 (12)	O3—C18—C17	119.52 (14)
C5—C6—H6A	120.8	O3—C18—C19	119.37 (14)
C7—C6—H6A	120.8	C17—C18—C19	121.04 (12)
O1—C7—C6	117.37 (11)	O3—C18—H18A	2.7
O1—C7—C2	120.27 (11)	C17—C18—H18A	119.5
C6—C7—C2	122.37 (12)	C19—C18—H18A	119.5
O2—C8—O1	115.71 (11)	C18—C19—C14	119.94 (12)
O2—C8—C9	126.15 (12)	C18—C19—H19A	120.0
O1—C8—C9	118.14 (11)	C14—C19—H19A	120.0
C1—C9—C8	119.05 (11)	C13—C20—H20A	109.5
C1—C9—C10	121.73 (11)	C13—C20—H20B	109.5
C8—C9—C10	119.22 (11)	H20A—C20—H20B	109.5
C11—C10—N1	115.28 (11)	C13—C20—H20C	109.5
C11—C10—C9	127.12 (11)	H20A—C20—H20C	109.5
N1—C10—C9	117.59 (10)	H20B—C20—H20C	109.5
C12—N2—N3—C13	−179.10 (12)	C8—C9—C10—N1	−177.98 (11)
C9—C1—C2—C7	0.02 (19)	N1—C10—C11—S1	0.55 (14)
C9—C1—C2—C3	−179.70 (13)	C9—C10—C11—S1	−179.34 (10)
C7—C2—C3—C4	−0.2 (2)	C12—S1—C11—C10	−0.43 (10)
C1—C2—C3—C4	179.48 (13)	C10—N1—C12—N2	179.60 (12)
C2—C3—C4—C5	−0.4 (2)	C10—N1—C12—S1	0.00 (14)
C3—C4—C5—C6	0.3 (2)	N3—N2—C12—N1	−178.57 (12)
C4—C5—C6—C7	0.28 (19)	N3—N2—C12—S1	1.03 (15)
C8—O1—C7—C6	178.55 (11)	C11—S1—C12—N1	0.26 (11)
C8—O1—C7—C2	−1.91 (17)	C11—S1—C12—N2	−179.37 (11)
C5—C6—C7—O1	178.62 (11)	N2—N3—C13—C14	178.40 (11)
C5—C6—C7—C2	−0.91 (19)	N2—N3—C13—C20	−0.57 (19)
C3—C2—C7—O1	−178.63 (11)	N3—C13—C14—C19	172.60 (12)
C1—C2—C7—O1	1.64 (18)	C20—C13—C14—C19	−8.40 (18)
C3—C2—C7—C6	0.89 (19)	N3—C13—C14—C15	−8.30 (17)
C1—C2—C7—C6	−178.84 (12)	C20—C13—C14—C15	170.69 (12)
C7—O1—C8—O2	−179.37 (11)	C19—C14—C15—C16	−0.43 (18)
C7—O1—C8—C9	0.49 (17)	C13—C14—C15—C16	−179.54 (11)
C2—C1—C9—C8	−1.41 (18)	C14—C15—C16—C17	1.10 (19)
C2—C1—C9—C10	178.93 (11)	C14—C15—C16—O3A	179.92 (16)
O2—C8—C9—C1	−178.99 (13)	C15—C16—C17—C18	−0.56 (19)
O1—C8—C9—C1	1.17 (17)	O3A—C16—C17—C18	−179.49 (15)
O2—C8—C9—C10	0.7 (2)	C16—C17—C18—O3	176.29 (14)
O1—C8—C9—C10	−179.16 (11)	C16—C17—C18—C19	−0.7 (2)
C12—N1—C10—C11	−0.35 (15)	O3—C18—C19—C14	−175.63 (14)
C12—N1—C10—C9	179.55 (11)	C17—C18—C19—C14	1.3 (2)
C1—C9—C10—C11	−178.43 (13)	C15—C14—C19—C18	−0.76 (18)
C8—C9—C10—C11	1.90 (19)	C13—C14—C19—C18	178.35 (12)
C1—C9—C10—N1	1.68 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1OA···O2i	0.89 (4)	1.89 (4)	2.7693 (19)	171 (4)
C19—H19A···O2i	0.93	2.59	3.3020 (17)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1OA⋯O2i	0.89 (4)	1.89 (4)	2.7693 (19)	171 (4)
C19—H19A⋯O2i	0.93	2.59	3.3020 (17)	133

Symmetry code: (i) .