Crystal structure of 4-((1E)-1-{(2Z)-2-[4-(4-bromo­phen­yl)-3-phenyl-2,3-di­hydro-1,3-thia­zol-2-yl­idene]hydrazin-1-yl­idene}eth­yl)phenol hemihydrate

Mague, J.T.; Akkurt, M.; Mohamed, S.K.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536814019473

organic compounds

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1124-o1125

doi:10.1107/S1600536814019473

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Crystal structure of 4-((1E)-1-{(2Z)-2-[4-(4-bromophenyl)-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene]hydrazin-1-ylidene}ethyl)phenol hemihydrate

Joel T. Mague,^a Mehmet Akkurt,^b Shaaban K. Mohamed,^c,^d Alaa A. Hassan ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^eChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. McArdle, National University of Ireland, Ireland (Received 18 July 2014; accepted 28 August 2014; online 24 September 2014)

In the title compound, C₂₃H₁₈BrN₃OS·0.5H₂O, the bromophenyl, 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 thiazolidene ring. In the crystal, the lattice water molecule is hydrogen bonded to the phenol group and makes a weaker O—H⋯N connection to an inversion-related molecule, forming a ring while weak pairwise C—H⋯S interactions involving inversion-related molecules form a second ring. Both these motifs result in the formation of two-dimensional networks lying parallel to (10-1).

Keywords: crystal structure; phenol; C—H⋯S interactions; thiazole scaffold compounds; medicinal applications.

CCDC reference: 1021529

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 ).

2. Experimental

2.1. Crystal data

C₂₃H₁₈BrN₃OS·0.5H₂O
M_r = 473.38
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 1.02
5211 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

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).

Supporting information

CCDC reference: 1021529

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814019473/qm2108sup1.cif

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

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

checkCIF report

Comment top

Thiazole scaffold compounds are of considerable interest from therapeutic point of view due to their utility as antibacterial and antifungal (Pattan et al., 2009), anti-inflammatory (Sharma et al., 2009), analgesic (Argyropoulou et al., 2009), antitubercular (Trautman & Longe, 1948), central nervous system (CNS) stimulate (Surray, 1949), anti-HIV (Bhattacharya et al., 2005), and algicidol (Alemagna et al., 1968) activities. Some of thiazole derivatives have shown inhibition towards herpes simplex virus (Spector et al., 1998). In addition, thiazole containing N=C=S moiety have been used as antiphychotics (Pattan et al., 2009) and antimalarial (Karade et al., 2008) agents. In this context and as part of our on-going study of bio-active heterocyclic molecules we herein report the synthesis and crystal structure of the title compound. In the title compound, the phenyl rings C1–C6, C10–C15 and C18–C23 make dihedral angles, respectively, of 46.5 (1), 66.78 (8) and 15.4 (2)° with the least squares plane of the thiazolidene ring. The lattice water is hydrogen bonded to the phenol group and makes a weaker connection to N2ⁱ (i: 2-x, 1-y, 1-z) to form a ring while weak, pairwise C17—H17B···S1 interactions with the molecule at 1-x, 1-y, 1-z form a second ring (Fig. 2 and Table 1). Both these motifs extend along (101).

Related literature top

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 top

The title compound has been prepared according to our reported method (Akkurt et al., 2014). Mono-crystals suitable for X-ray diffraction have been obtained by crystallization of the crude product (I) from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).

Figures top

	Fig. 1. The title compound with numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. 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.

4-((1E)-1-{(2Z)-2-[4-(4-Bromophenyl)-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene]hydrazin-1-ylidene}ethyl)phenol hemihydrate top

Crystal data top

C₂₃H₁₈BrN₃OS·0.5H₂O	Z = 2
M_r = 473.38	F(000) = 482
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.062P)² + 0.5209P] where P = (F_o² + 2F_c²)/3
5211 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₃H₁₈BrN₃OS·0.5H₂O	γ = 86.249 (4)°
M_r = 473.38	V = 1040.3 (4) Å³
Triclinic, P1	Z = 2
a = 8.485 (2) Å	Mo Kα radiation
b = 10.336 (2) Å	µ = 2.10 mm⁻¹
c = 12.057 (3) Å	T = 150 K
α = 80.515 (3)°	0.27 × 0.23 × 0.07 mm
β = 88.008 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	5211 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	3834 reflections with I > 2σ(I)
T_min = 0.51, T_max = 0.86	R_int = 0.049
18957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	Δρ_max = 0.85 e Å⁻³
5211 reflections	Δρ_min = −0.32 e Å⁻³
273 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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Volume 70| Part 10| October 2014| Pages o1124-o1125

doi:10.1107/S1600536814019473

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4-((1E)-1-{(2Z)-2-[4-(4-bromo­phen­yl)-3-phenyl-2,3-di­hydro-1,3-thia­zol-2-yl­­idene]hydrazin-1-yl­­idene}eth­yl)phenol hemihydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4-((1E)-1-{(2Z)-2-[4-(4-bromophenyl)-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene]hydrazin-1-ylidene}ethyl)phenol hemihydrate