Crystal structure of 4-((1E)-1-{(2Z)-2-[4-(4-bromo-phen-yl)-3-phenyl-2,3-di-hydro-1,3-thia-zol-2-yl-idene]hydrazin-1-yl-idene}eth-yl)phenol hemihydrate.

In the title compound, C23H18BrN3OS·0.5H2O, the bromo-phenyl, phenyl and phenol rings make dihedral angles of 46.5 (1), 66.78 (8) and 15.4 (2)°, respectively, with the mean squares plane of the thia-zol-idene ring. In the crystal, the lattice water mol-ecule is hydrogen bonded to the phenol group and makes a weaker O-H⋯N connection to an inversion-related mol-ecule, forming a ring while weak pairwise C-H⋯S inter-actions involving inversion-related mol-ecules form a second ring. Both these motifs result in the formation of two-dimensional networks lying parallel to (10-1).

Related literature

For the wide spectrum of medicinal applications of thia­zole scaffold compounds, see: Pattan et al. (2009 ▶); Sharma et al. (2009 ▶); Argyropoulou et al. (2009 ▶); Trautman & Longe (1948 ▶); Surray (1949 ▶); Bhattacharya et al. (2005 ▶); Alemagna et al. (1968 ▶); Spector et al. (1998 ▶); Karade et al. (2008 ▶). For a related structure, see: Akkurt et al. (2014 ▶).

Experimental

Crystal data

C23H18BrN3OS·0.5H2O

M = 473.38

Triclinic,

a = 8.485 (2) Å

b = 10.336 (2) Å

c = 12.057 (3) Å

α = 80.515 (3)°

β = 88.008 (3)°

γ = 86.249 (4)°

V = 1040.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.10 mm−1

T = 150 K

0.27 × 0.23 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.51, T max = 0.86

18957 measured reflections

5211 independent reflections

3834 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.02

5211 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814019473/qm2108sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019473/qm2108Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019473/qm2108Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019473/qm2108fig1.tif

The title compound with numbering scheme and 50% probability displacement ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S1600536814019473/qm2108fig2.tif

Packing viewed down the b axis showing the rings formed by the O—H⋯O (red), O—H⋯N (blue) and C—H⋯S (black) inter­actions.

CCDC reference: 1021529

Additional supporting information: crystallographic information; 3D view; checkCIF report

C23H18BrN3OS·0.5H2O	Z = 2
Mr = 473.38	F(000) = 482
Triclinic, P1	Dx = 1.511 Mg m−3
a = 8.485 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.336 (2) Å	Cell parameters from 7895 reflections
c = 12.057 (3) Å	θ = 2.4–28.4°
α = 80.515 (3)°	µ = 2.10 mm−1
β = 88.008 (3)°	T = 150 K
γ = 86.249 (4)°	Plate, orange
V = 1040.3 (4) Å3	0.27 × 0.23 × 0.07 mm

Bruker SMART APEX CCD diffractometer	5211 independent reflections
Radiation source: fine-focus sealed tube	3834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.3660 pixels mm-1	θmax = 28.5°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −13→13
Tmin = 0.51, Tmax = 0.86	l = −16→16
18957 measured reflections

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)] = 0.046	Hydrogen site location: mixed
wR(F2) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.062P)2 + 0.5209P] where P = (Fo2 + 2Fc2)/3
5211 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to oxygen were placed in locations derived from a difference map and their coordinates adjusted to give O—H = 0.84 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	−0.12028 (5)	0.13286 (3)	−0.19996 (3)	0.05610 (15)
S1	0.40464 (9)	0.58630 (7)	0.18323 (6)	0.03452 (17)
O1	0.9721 (3)	0.8848 (3)	0.5879 (3)	0.0730 (8)
H1	1.0394	0.8562	0.6368	0.110*
N1	0.3970 (3)	0.3403 (2)	0.16873 (18)	0.0301 (5)
N2	0.5690 (3)	0.3796 (2)	0.3070 (2)	0.0369 (5)
N3	0.6250 (3)	0.4875 (2)	0.34845 (19)	0.0354 (5)
C1	0.1997 (3)	0.3384 (3)	0.0175 (2)	0.0290 (5)
C2	0.1835 (3)	0.3850 (3)	−0.0973 (2)	0.0347 (6)
H2	0.2382	0.4593	−0.1313	0.042*
C3	0.0891 (3)	0.3245 (3)	−0.1624 (2)	0.0370 (6)
H3	0.0798	0.3562	−0.2406	0.044*
C4	0.0090 (3)	0.2178 (3)	−0.1119 (2)	0.0374 (6)
C5	0.0177 (3)	0.1714 (3)	0.0027 (2)	0.0357 (6)
H5	−0.0417	0.0999	0.0366	0.043*
C6	0.1144 (3)	0.2311 (3)	0.0667 (2)	0.0343 (6)
H6	0.1231	0.1990	0.1449	0.041*
C7	0.2959 (3)	0.4075 (3)	0.0851 (2)	0.0296 (5)
C8	0.2881 (3)	0.5384 (3)	0.0827 (2)	0.0336 (6)
H8	0.2256	0.5985	0.0314	0.040*
C9	0.4677 (3)	0.4211 (3)	0.2289 (2)	0.0319 (6)
C10	0.4530 (3)	0.2040 (3)	0.1771 (2)	0.0304 (5)
C11	0.4261 (3)	0.1177 (3)	0.2750 (3)	0.0396 (7)
H11	0.3673	0.1464	0.3359	0.048*
C12	0.4863 (4)	−0.0122 (3)	0.2834 (3)	0.0457 (8)
H12	0.4673	−0.0727	0.3501	0.055*
C13	0.5730 (4)	−0.0532 (3)	0.1955 (3)	0.0460 (8)
H13	0.6136	−0.1419	0.2018	0.055*
C14	0.6010 (4)	0.0336 (3)	0.0988 (3)	0.0426 (7)
H14	0.6619	0.0052	0.0388	0.051*
C15	0.5403 (3)	0.1627 (3)	0.0889 (2)	0.0369 (6)
H15	0.5586	0.2227	0.0217	0.044*
C16	0.6881 (3)	0.4600 (3)	0.4462 (2)	0.0321 (6)
C17	0.6960 (4)	0.3259 (3)	0.5167 (2)	0.0383 (6)
H17A	0.6467	0.2643	0.4769	0.058*
H17B	0.6399	0.3296	0.5886	0.058*
H17C	0.8067	0.2963	0.5305	0.058*
C18	0.7578 (3)	0.5707 (3)	0.4874 (2)	0.0332 (6)
C19	0.7384 (4)	0.6989 (3)	0.4292 (3)	0.0410 (7)
H19	0.6745	0.7152	0.3646	0.049*
C20	0.8087 (4)	0.8027 (3)	0.4621 (3)	0.0483 (8)
H20	0.7939	0.8886	0.4201	0.058*
C21	0.9007 (4)	0.7810 (3)	0.5567 (3)	0.0483 (8)
C22	0.9198 (4)	0.6557 (3)	0.6184 (3)	0.0455 (7)
H22	0.9815	0.6406	0.6840	0.055*
C23	0.8486 (3)	0.5521 (3)	0.5839 (2)	0.0379 (6)
H23	0.8620	0.4666	0.6270	0.045*
O2	1.1835 (4)	0.8167 (5)	0.7301 (4)	0.0451 (11)	0.5
H2A	1.2451	0.8144	0.6743	0.054*	0.5
H2B	1.1914	0.7404	0.7668	0.054*	0.5

	U11	U22	U33	U12	U13	U23
Br1	0.0777 (3)	0.0379 (2)	0.0543 (2)	−0.00352 (16)	−0.03883 (18)	−0.00462 (14)
S1	0.0432 (4)	0.0256 (3)	0.0347 (4)	−0.0034 (3)	−0.0061 (3)	−0.0030 (3)
O1	0.0642 (17)	0.0498 (16)	0.114 (3)	−0.0017 (13)	−0.0168 (16)	−0.0361 (16)
N1	0.0385 (12)	0.0249 (11)	0.0263 (11)	−0.0011 (9)	−0.0074 (9)	−0.0010 (8)
N2	0.0451 (13)	0.0337 (13)	0.0319 (12)	−0.0062 (10)	−0.0093 (10)	−0.0017 (10)
N3	0.0430 (13)	0.0340 (13)	0.0296 (12)	−0.0060 (10)	−0.0082 (10)	−0.0032 (9)
C1	0.0294 (12)	0.0261 (13)	0.0301 (13)	0.0052 (10)	−0.0044 (10)	−0.0028 (10)
C2	0.0343 (14)	0.0335 (15)	0.0332 (14)	0.0016 (11)	−0.0020 (11)	0.0018 (11)
C3	0.0408 (15)	0.0381 (16)	0.0303 (14)	0.0058 (12)	−0.0102 (12)	−0.0014 (11)
C4	0.0424 (15)	0.0304 (15)	0.0404 (15)	0.0074 (12)	−0.0170 (12)	−0.0091 (12)
C5	0.0437 (15)	0.0242 (13)	0.0386 (15)	−0.0005 (11)	−0.0093 (12)	−0.0019 (11)
C6	0.0433 (15)	0.0288 (14)	0.0294 (13)	−0.0003 (11)	−0.0054 (11)	−0.0008 (10)
C7	0.0319 (13)	0.0263 (13)	0.0292 (13)	−0.0002 (10)	−0.0031 (10)	−0.0003 (10)
C8	0.0357 (14)	0.0272 (14)	0.0367 (15)	0.0005 (11)	−0.0076 (11)	−0.0007 (11)
C9	0.0386 (14)	0.0285 (13)	0.0278 (13)	−0.0039 (11)	−0.0016 (11)	−0.0012 (10)
C10	0.0319 (13)	0.0246 (13)	0.0338 (14)	−0.0020 (10)	−0.0096 (11)	0.0004 (10)
C11	0.0404 (15)	0.0365 (16)	0.0384 (16)	0.0003 (12)	0.0003 (13)	0.0029 (12)
C12	0.0494 (17)	0.0319 (16)	0.0494 (18)	0.0003 (13)	−0.0087 (14)	0.0127 (13)
C13	0.0480 (17)	0.0315 (16)	0.058 (2)	0.0078 (13)	−0.0207 (15)	−0.0061 (14)
C14	0.0451 (17)	0.0420 (17)	0.0427 (17)	0.0022 (13)	−0.0085 (13)	−0.0134 (13)
C15	0.0424 (15)	0.0361 (15)	0.0322 (14)	−0.0024 (12)	−0.0048 (12)	−0.0047 (11)
C16	0.0351 (13)	0.0347 (15)	0.0245 (13)	0.0028 (11)	−0.0026 (10)	−0.0005 (10)
C17	0.0488 (16)	0.0353 (15)	0.0297 (14)	0.0007 (13)	−0.0087 (12)	−0.0013 (11)
C18	0.0321 (13)	0.0376 (15)	0.0294 (13)	0.0011 (11)	−0.0031 (11)	−0.0047 (11)
C19	0.0455 (16)	0.0392 (17)	0.0382 (16)	0.0023 (13)	−0.0087 (13)	−0.0063 (13)
C20	0.0512 (18)	0.0372 (17)	0.057 (2)	0.0005 (14)	−0.0099 (15)	−0.0074 (14)
C21	0.0410 (16)	0.0482 (19)	0.061 (2)	0.0012 (14)	−0.0070 (15)	−0.0239 (16)
C22	0.0374 (15)	0.058 (2)	0.0430 (17)	0.0024 (14)	−0.0106 (13)	−0.0152 (15)
C23	0.0360 (14)	0.0442 (17)	0.0332 (15)	0.0004 (12)	−0.0038 (12)	−0.0057 (12)
O2	0.0275 (19)	0.060 (3)	0.057 (3)	0.0017 (18)	−0.0138 (18)	−0.035 (2)

Br1—C4	1.902 (3)	C11—C12	1.394 (4)
S1—C8	1.743 (3)	C11—H11	0.9500
S1—C9	1.760 (3)	C12—C13	1.377 (5)
O1—C21	1.376 (4)	C12—H12	0.9500
O1—H1	0.8400	C13—C14	1.372 (5)
N1—C9	1.371 (3)	C13—H13	0.9500
N1—C7	1.409 (3)	C14—C15	1.387 (4)
N1—C10	1.446 (3)	C14—H14	0.9500
N2—C9	1.297 (4)	C15—H15	0.9500
N2—N3	1.411 (3)	C16—C18	1.484 (4)
N3—C16	1.293 (3)	C16—C17	1.500 (4)
C1—C2	1.397 (4)	C17—H17A	0.9800
C1—C6	1.401 (4)	C17—H17B	0.9800
C1—C7	1.467 (4)	C17—H17C	0.9800
C2—C3	1.385 (4)	C18—C19	1.396 (4)
C2—H2	0.9500	C18—C23	1.397 (4)
C3—C4	1.377 (4)	C19—C20	1.380 (5)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.388 (4)	C20—C21	1.384 (5)
C5—C6	1.385 (4)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.386 (5)
C6—H6	0.9500	C22—C23	1.391 (4)
C7—C8	1.346 (4)	C22—H22	0.9500
C8—H8	0.9500	C23—H23	0.9500
C10—C11	1.379 (4)	O2—H2A	0.8397
C10—C15	1.384 (4)	O2—H2B	0.8384
C8—S1—C9	90.06 (13)	C13—C12—C11	120.4 (3)
C21—O1—H1	109.5	C13—C12—H12	119.8
C9—N1—C7	114.0 (2)	C11—C12—H12	119.8
C9—N1—C10	119.9 (2)	C14—C13—C12	120.2 (3)
C7—N1—C10	124.7 (2)	C14—C13—H13	119.9
C9—N2—N3	109.8 (2)	C12—C13—H13	119.9
C16—N3—N2	115.3 (2)	C13—C14—C15	120.0 (3)
C2—C1—C6	118.6 (2)	C13—C14—H14	120.0
C2—C1—C7	119.8 (2)	C15—C14—H14	120.0
C6—C1—C7	121.6 (2)	C10—C15—C14	119.8 (3)
C3—C2—C1	121.1 (3)	C10—C15—H15	120.1
C3—C2—H2	119.5	C14—C15—H15	120.1
C1—C2—H2	119.5	N3—C16—C18	116.0 (2)
C4—C3—C2	118.9 (3)	N3—C16—C17	124.2 (3)
C4—C3—H3	120.6	C18—C16—C17	119.8 (2)
C2—C3—H3	120.6	C16—C17—H17A	109.5
C3—C4—C5	121.8 (3)	C16—C17—H17B	109.5
C3—C4—Br1	119.5 (2)	H17A—C17—H17B	109.5
C5—C4—Br1	118.7 (2)	C16—C17—H17C	109.5
C6—C5—C4	118.9 (3)	H17A—C17—H17C	109.5
C6—C5—H5	120.6	H17B—C17—H17C	109.5
C4—C5—H5	120.6	C19—C18—C23	116.8 (3)
C5—C6—C1	120.8 (3)	C19—C18—C16	121.0 (2)
C5—C6—H6	119.6	C23—C18—C16	122.2 (3)
C1—C6—H6	119.6	C20—C19—C18	122.3 (3)
C8—C7—N1	112.4 (2)	C20—C19—H19	118.9
C8—C7—C1	125.0 (2)	C18—C19—H19	118.9
N1—C7—C1	122.4 (2)	C19—C20—C21	119.7 (3)
C7—C8—S1	113.1 (2)	C19—C20—H20	120.2
C7—C8—H8	123.5	C21—C20—H20	120.2
S1—C8—H8	123.5	O1—C21—C20	119.2 (3)
N2—C9—N1	123.9 (2)	O1—C21—C22	121.0 (3)
N2—C9—S1	125.6 (2)	C20—C21—C22	119.8 (3)
N1—C9—S1	110.52 (19)	C21—C22—C23	119.9 (3)
C11—C10—C15	120.5 (3)	C21—C22—H22	120.1
C11—C10—N1	119.8 (2)	C23—C22—H22	120.1
C15—C10—N1	119.6 (2)	C22—C23—C18	121.5 (3)
C10—C11—C12	119.1 (3)	C22—C23—H23	119.2
C10—C11—H11	120.5	C18—C23—H23	119.2
C12—C11—H11	120.5	H2A—O2—H2B	104.8
C9—N2—N3—C16	160.3 (2)	C8—S1—C9—N1	−1.1 (2)
C6—C1—C2—C3	−1.9 (4)	C9—N1—C10—C11	70.7 (3)
C7—C1—C2—C3	−177.8 (2)	C7—N1—C10—C11	−123.7 (3)
C1—C2—C3—C4	0.8 (4)	C9—N1—C10—C15	−105.9 (3)
C2—C3—C4—C5	1.5 (4)	C7—N1—C10—C15	59.7 (4)
C2—C3—C4—Br1	−179.6 (2)	C15—C10—C11—C12	−0.8 (4)
C3—C4—C5—C6	−2.5 (4)	N1—C10—C11—C12	−177.5 (3)
Br1—C4—C5—C6	178.6 (2)	C10—C11—C12—C13	0.8 (5)
C4—C5—C6—C1	1.3 (4)	C11—C12—C13—C14	0.0 (5)
C2—C1—C6—C5	0.8 (4)	C12—C13—C14—C15	−0.7 (5)
C7—C1—C6—C5	176.6 (2)	C11—C10—C15—C14	0.1 (4)
C9—N1—C7—C8	−0.9 (3)	N1—C10—C15—C14	176.8 (3)
C10—N1—C7—C8	−167.2 (2)	C13—C14—C15—C10	0.7 (4)
C9—N1—C7—C1	−175.1 (2)	N2—N3—C16—C18	175.8 (2)
C10—N1—C7—C1	18.5 (4)	N2—N3—C16—C17	−3.3 (4)
C2—C1—C7—C8	46.9 (4)	N3—C16—C18—C19	7.3 (4)
C6—C1—C7—C8	−128.9 (3)	C17—C16—C18—C19	−173.5 (3)
C2—C1—C7—N1	−139.6 (3)	N3—C16—C18—C23	−171.0 (3)
C6—C1—C7—N1	44.6 (4)	C17—C16—C18—C23	8.1 (4)
N1—C7—C8—S1	0.0 (3)	C23—C18—C19—C20	1.9 (4)
C1—C7—C8—S1	174.1 (2)	C16—C18—C19—C20	−176.5 (3)
C9—S1—C8—C7	0.6 (2)	C18—C19—C20—C21	−0.7 (5)
N3—N2—C9—N1	177.1 (2)	C19—C20—C21—O1	179.1 (3)
N3—N2—C9—S1	−1.5 (3)	C19—C20—C21—C22	−0.9 (5)
C7—N1—C9—N2	−177.5 (3)	O1—C21—C22—C23	−178.9 (3)
C10—N1—C9—N2	−10.4 (4)	C20—C21—C22—C23	1.0 (5)
C7—N1—C9—S1	1.3 (3)	C21—C22—C23—C18	0.3 (5)
C10—N1—C9—S1	168.41 (19)	C19—C18—C23—C22	−1.7 (4)
C8—S1—C9—N2	177.7 (3)	C16—C18—C23—C22	176.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.67	2.511 (5)	173
O2—H2A···N2i	0.84	2.45	2.898 (5)	114
C17—H17B···S1ii	0.98	3.02	3.925 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	1.67	2.511 (5)	173
O2—H2A⋯N2i	0.84	2.45	2.898 (5)	114
C17—H17B⋯S1ii	0.98	3.02	3.925 (3)	154

Symmetry codes: (i) ; (ii) .