(E)-6-Bromo-3-{2-[2-(2-meth-oxy-benzyl-idene)hydrazin-yl]-1,3-thia-zol-4-yl}-2H-chromen-2-one.

In the title compound, C(20)H(14)BrN(3)O(3)S, the mol-ecule adopts an E configuration about the central C=N double bond. The chromene ring system and the thia-zole ring are approximately planar [maximum deviations = 0.029 (3) and 0.007 (3) Å, respectively]. The chromene ring system is inclined at angles of 7.37 (12) and 13.90 (13)° with respect to the thia-zole and benzene rings, respectively, while the thia-zole ring makes a dihedral angle of 12.58 (15)° with the benzene ring. In the crystal, mol-ecules are connected by N-H⋯O hydrogen bonds, forming C(8) supra-molecular chains along the c axis.

Related literature

For related structures, further synthetic details and background references, see: Arshad et al. (2011 ▶).

Experimental

Crystal data

C20H14BrN3O3S

M = 456.31

Monoclinic,

a = 7.2802 (12) Å

b = 19.551 (3) Å

c = 14.0638 (18) Å

β = 113.352 (7)°

V = 1837.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.38 mm−1

T = 296 K

0.43 × 0.07 × 0.04 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.427, T max = 0.921

11951 measured reflections

4266 independent reflections

2786 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.089

S = 1.01

4266 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.29 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/S1600536811024536/hb5923sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024536/hb5923Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024536/hb5923Isup3.cml

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

C20H14BrN3O3S	F(000) = 920
Mr = 456.31	Dx = 1.649 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2197 reflections
a = 7.2802 (12) Å	θ = 3.0–22.4°
b = 19.551 (3) Å	µ = 2.38 mm−1
c = 14.0638 (18) Å	T = 296 K
β = 113.352 (7)°	Needle, yellow
V = 1837.8 (5) Å3	0.43 × 0.07 × 0.04 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	4266 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.427, Tmax = 0.921	k = −25→24
11951 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.034P)2 + 0.488P] where P = (Fo2 + 2Fc2)/3
4266 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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 > 2sigma(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
Br1	0.24394 (5)	1.084300 (17)	0.06129 (3)	0.06481 (13)
S1	0.21746 (11)	0.61887 (3)	0.38892 (5)	0.04655 (18)
O1	0.2719 (3)	0.92795 (9)	0.43367 (12)	0.0453 (4)
O2	0.2679 (3)	0.83501 (10)	0.51902 (14)	0.0567 (5)
O3	0.2197 (3)	0.37198 (9)	0.04438 (13)	0.0518 (5)
N1	0.2186 (3)	0.71059 (10)	0.25691 (15)	0.0403 (5)
N2	0.2131 (3)	0.59752 (10)	0.19923 (16)	0.0459 (6)
H1	0.2264	0.6102	0.1375	0.055*
N3	0.2291 (3)	0.53132 (10)	0.23123 (16)	0.0397 (5)
C1	0.2567 (4)	0.85797 (13)	0.43706 (19)	0.0402 (6)
C2	0.2663 (4)	0.96192 (13)	0.34700 (19)	0.0407 (6)
C3	0.2939 (4)	1.03179 (15)	0.3551 (2)	0.0515 (7)
H3A	0.3160	1.0541	0.4171	0.062*
C4	0.2880 (4)	1.06785 (14)	0.2703 (2)	0.0523 (7)
H4A	0.3068	1.1150	0.2744	0.063*
C5	0.2538 (4)	1.03353 (14)	0.1781 (2)	0.0446 (6)
C6	0.2293 (4)	0.96446 (14)	0.1706 (2)	0.0439 (6)
H6A	0.2081	0.9424	0.1085	0.053*
C7	0.2358 (4)	0.92670 (12)	0.25618 (18)	0.0372 (6)
C8	0.2190 (4)	0.85417 (13)	0.25783 (19)	0.0401 (6)
H8A	0.1991	0.8297	0.1978	0.048*
C9	0.2310 (4)	0.81934 (13)	0.34368 (18)	0.0372 (6)
C10	0.2232 (4)	0.74489 (13)	0.34487 (18)	0.0366 (6)
C11	0.2234 (4)	0.70361 (13)	0.42228 (19)	0.0430 (6)
H11A	0.2264	0.7192	0.4854	0.052*
C12	0.2177 (4)	0.64534 (12)	0.27085 (18)	0.0363 (6)
C13	0.2343 (4)	0.48370 (12)	0.17014 (19)	0.0375 (6)
H13A	0.2209	0.4934	0.1030	0.045*
C14	0.2620 (4)	0.41341 (12)	0.20920 (18)	0.0348 (5)
C15	0.3017 (4)	0.40043 (13)	0.3125 (2)	0.0445 (6)
H15A	0.3043	0.4367	0.3559	0.053*
C16	0.3374 (5)	0.33511 (14)	0.3522 (2)	0.0544 (8)
H16A	0.3618	0.3275	0.4215	0.065*
C17	0.3368 (5)	0.28129 (14)	0.2896 (2)	0.0557 (8)
H17A	0.3650	0.2374	0.3170	0.067*
C18	0.2947 (4)	0.29182 (13)	0.1862 (2)	0.0479 (7)
H18A	0.2917	0.2550	0.1437	0.057*
C19	0.2572 (4)	0.35707 (13)	0.14584 (18)	0.0376 (6)
C20	0.2017 (5)	0.31519 (14)	−0.0228 (2)	0.0530 (7)
H20A	0.1687	0.3315	−0.0920	0.080*
H20B	0.0979	0.2852	−0.0220	0.080*
H20C	0.3262	0.2908	0.0005	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0782 (2)	0.0614 (2)	0.0665 (2)	−0.00399 (17)	0.04110 (19)	0.01182 (16)
S1	0.0669 (5)	0.0376 (4)	0.0421 (4)	−0.0001 (3)	0.0291 (3)	0.0017 (3)
O1	0.0660 (12)	0.0354 (10)	0.0349 (10)	0.0021 (9)	0.0203 (9)	−0.0065 (8)
O2	0.0930 (16)	0.0460 (11)	0.0367 (11)	0.0041 (10)	0.0315 (11)	−0.0039 (9)
O3	0.0867 (14)	0.0353 (10)	0.0391 (10)	−0.0008 (10)	0.0310 (10)	−0.0042 (8)
N1	0.0546 (13)	0.0317 (12)	0.0366 (12)	−0.0013 (10)	0.0202 (10)	−0.0057 (9)
N2	0.0760 (16)	0.0297 (12)	0.0394 (12)	−0.0014 (11)	0.0307 (12)	−0.0028 (9)
N3	0.0529 (13)	0.0285 (11)	0.0404 (12)	−0.0002 (10)	0.0213 (10)	−0.0002 (9)
C1	0.0459 (15)	0.0371 (15)	0.0377 (14)	0.0032 (12)	0.0167 (12)	−0.0057 (12)
C2	0.0451 (15)	0.0357 (15)	0.0408 (15)	0.0018 (12)	0.0166 (12)	−0.0033 (12)
C3	0.0630 (19)	0.0439 (17)	0.0441 (16)	−0.0017 (14)	0.0176 (14)	−0.0127 (13)
C4	0.0640 (19)	0.0327 (15)	0.0591 (18)	−0.0057 (14)	0.0234 (16)	−0.0050 (13)
C5	0.0454 (16)	0.0408 (16)	0.0516 (16)	0.0001 (13)	0.0235 (13)	0.0055 (13)
C6	0.0511 (16)	0.0444 (16)	0.0398 (15)	−0.0008 (13)	0.0219 (13)	−0.0045 (12)
C7	0.0410 (14)	0.0340 (14)	0.0366 (14)	0.0012 (11)	0.0155 (12)	−0.0064 (11)
C8	0.0481 (16)	0.0386 (15)	0.0349 (14)	−0.0009 (12)	0.0179 (12)	−0.0093 (11)
C9	0.0400 (14)	0.0367 (14)	0.0359 (14)	0.0016 (11)	0.0159 (12)	−0.0077 (11)
C10	0.0391 (14)	0.0369 (14)	0.0336 (13)	0.0012 (11)	0.0141 (11)	−0.0066 (11)
C11	0.0578 (17)	0.0398 (15)	0.0356 (14)	0.0011 (13)	0.0231 (13)	−0.0046 (11)
C12	0.0444 (15)	0.0334 (14)	0.0324 (13)	−0.0006 (11)	0.0165 (12)	−0.0026 (11)
C13	0.0485 (15)	0.0327 (14)	0.0336 (13)	−0.0012 (12)	0.0187 (12)	−0.0011 (11)
C14	0.0400 (13)	0.0296 (13)	0.0376 (14)	−0.0030 (11)	0.0184 (11)	−0.0013 (11)
C15	0.0605 (18)	0.0359 (15)	0.0404 (15)	−0.0032 (13)	0.0236 (14)	−0.0031 (12)
C16	0.082 (2)	0.0437 (17)	0.0405 (16)	0.0001 (15)	0.0280 (16)	0.0043 (13)
C17	0.079 (2)	0.0344 (15)	0.0556 (18)	0.0057 (15)	0.0293 (17)	0.0109 (13)
C18	0.0691 (19)	0.0311 (15)	0.0502 (16)	−0.0027 (13)	0.0309 (15)	−0.0047 (12)
C19	0.0454 (15)	0.0337 (14)	0.0380 (14)	−0.0032 (11)	0.0211 (12)	−0.0013 (11)
C20	0.073 (2)	0.0473 (17)	0.0419 (16)	−0.0035 (15)	0.0259 (15)	−0.0133 (13)

Br1—C5	1.896 (3)	C6—H6A	0.9300
S1—C11	1.718 (3)	C7—C8	1.424 (3)
S1—C12	1.740 (2)	C8—C9	1.359 (3)
O1—C2	1.375 (3)	C8—H8A	0.9300
O1—C1	1.375 (3)	C9—C10	1.457 (3)
O2—C1	1.209 (3)	C10—C11	1.355 (3)
O3—C19	1.374 (3)	C11—H11A	0.9300
O3—C20	1.430 (3)	C13—C14	1.464 (3)
N1—C12	1.291 (3)	C13—H13A	0.9300
N1—C10	1.396 (3)	C14—C15	1.387 (3)
N2—N3	1.360 (3)	C14—C19	1.409 (3)
N2—C12	1.365 (3)	C15—C16	1.377 (4)
N2—H1	0.9449	C15—H15A	0.9300
N3—C13	1.277 (3)	C16—C17	1.371 (4)
C1—C9	1.461 (3)	C16—H16A	0.9300
C2—C3	1.379 (4)	C17—C18	1.377 (4)
C2—C7	1.389 (3)	C17—H17A	0.9300
C3—C4	1.371 (4)	C18—C19	1.379 (3)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.392 (4)	C20—H20A	0.9600
C4—H4A	0.9300	C20—H20B	0.9600
C5—C6	1.361 (4)	C20—H20C	0.9600
C6—C7	1.397 (3)
C11—S1—C12	87.96 (12)	C11—C10—C9	128.1 (2)
C2—O1—C1	122.48 (18)	N1—C10—C9	117.2 (2)
C19—O3—C20	116.75 (19)	C10—C11—S1	111.30 (18)
C12—N1—C10	109.9 (2)	C10—C11—H11A	124.4
N3—N2—C12	115.7 (2)	S1—C11—H11A	124.4
N3—N2—H1	121.9	N1—C12—N2	124.4 (2)
C12—N2—H1	121.1	N1—C12—S1	116.16 (17)
C13—N3—N2	119.5 (2)	N2—C12—S1	119.44 (18)
O2—C1—O1	115.2 (2)	N3—C13—C14	117.9 (2)
O2—C1—C9	126.9 (2)	N3—C13—H13A	121.0
O1—C1—C9	117.8 (2)	C14—C13—H13A	121.0
O1—C2—C3	116.9 (2)	C15—C14—C19	117.5 (2)
O1—C2—C7	120.9 (2)	C15—C14—C13	120.3 (2)
C3—C2—C7	122.1 (2)	C19—C14—C13	122.1 (2)
C4—C3—C2	118.9 (2)	C16—C15—C14	121.5 (2)
C4—C3—H3A	120.5	C16—C15—H15A	119.3
C2—C3—H3A	120.5	C14—C15—H15A	119.3
C3—C4—C5	119.6 (3)	C17—C16—C15	119.9 (3)
C3—C4—H4A	120.2	C17—C16—H16A	120.0
C5—C4—H4A	120.2	C15—C16—H16A	120.0
C6—C5—C4	121.4 (2)	C16—C17—C18	120.4 (3)
C6—C5—Br1	119.5 (2)	C16—C17—H17A	119.8
C4—C5—Br1	119.1 (2)	C18—C17—H17A	119.8
C5—C6—C7	119.9 (2)	C17—C18—C19	119.8 (2)
C5—C6—H6A	120.0	C17—C18—H18A	120.1
C7—C6—H6A	120.0	C19—C18—H18A	120.1
C2—C7—C6	118.0 (2)	O3—C19—C18	123.3 (2)
C2—C7—C8	117.5 (2)	O3—C19—C14	115.9 (2)
C6—C7—C8	124.5 (2)	C18—C19—C14	120.8 (2)
C9—C8—C7	122.5 (2)	O3—C20—H20A	109.5
C9—C8—H8A	118.7	O3—C20—H20B	109.5
C7—C8—H8A	118.7	H20A—C20—H20B	109.5
C8—C9—C10	121.4 (2)	O3—C20—H20C	109.5
C8—C9—C1	118.7 (2)	H20A—C20—H20C	109.5
C10—C9—C1	119.9 (2)	H20B—C20—H20C	109.5
C11—C10—N1	114.7 (2)
C12—N2—N3—C13	−177.2 (2)	C1—C9—C10—C11	4.9 (4)
C2—O1—C1—O2	178.6 (2)	C8—C9—C10—N1	4.9 (4)
C2—O1—C1—C9	−0.9 (3)	C1—C9—C10—N1	−173.7 (2)
C1—O1—C2—C3	−176.6 (2)	N1—C10—C11—S1	−0.1 (3)
C1—O1—C2—C7	2.9 (4)	C9—C10—C11—S1	−178.8 (2)
O1—C2—C3—C4	−179.5 (3)	C12—S1—C11—C10	0.6 (2)
C7—C2—C3—C4	1.0 (4)	C10—N1—C12—N2	179.9 (2)
C2—C3—C4—C5	0.3 (4)	C10—N1—C12—S1	1.2 (3)
C3—C4—C5—C6	−1.1 (4)	N3—N2—C12—N1	174.9 (2)
C3—C4—C5—Br1	179.5 (2)	N3—N2—C12—S1	−6.4 (3)
C4—C5—C6—C7	0.8 (4)	C11—S1—C12—N1	−1.1 (2)
Br1—C5—C6—C7	−179.84 (19)	C11—S1—C12—N2	−179.8 (2)
O1—C2—C7—C6	179.2 (2)	N2—N3—C13—C14	176.9 (2)
C3—C2—C7—C6	−1.3 (4)	N3—C13—C14—C15	−6.5 (4)
O1—C2—C7—C8	−2.6 (4)	N3—C13—C14—C19	176.0 (2)
C3—C2—C7—C8	176.9 (2)	C19—C14—C15—C16	0.7 (4)
C5—C6—C7—C2	0.4 (4)	C13—C14—C15—C16	−177.0 (3)
C5—C6—C7—C8	−177.7 (2)	C14—C15—C16—C17	0.9 (5)
C2—C7—C8—C9	0.3 (4)	C15—C16—C17—C18	−2.0 (5)
C6—C7—C8—C9	178.4 (3)	C16—C17—C18—C19	1.4 (5)
C7—C8—C9—C10	−176.9 (2)	C20—O3—C19—C18	5.8 (4)
C7—C8—C9—C1	1.7 (4)	C20—O3—C19—C14	−176.2 (2)
O2—C1—C9—C8	179.2 (3)	C17—C18—C19—O3	178.1 (3)
O1—C1—C9—C8	−1.4 (4)	C17—C18—C19—C14	0.2 (4)
O2—C1—C9—C10	−2.1 (4)	C15—C14—C19—O3	−179.3 (2)
O1—C1—C9—C10	177.3 (2)	C13—C14—C19—O3	−1.7 (4)
C12—N1—C10—C11	−0.7 (3)	C15—C14—C19—C18	−1.3 (4)
C12—N1—C10—C9	178.2 (2)	C13—C14—C19—C18	176.4 (2)
C8—C9—C10—C11	−176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O2i	0.94	2.10	3.021 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O2i	0.94	2.10	3.021 (3)	164

Symmetry code: (i) .