(Z)-1-[(2E)-3,4-Diphenyl-2,3-di­hydro-1,3-thia­zol-2-yl­idene]-2-[1-(4-hy­droxy­phen­yl)ethyl­idene]hydrazinium bromide including an unknown solvate

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

doi:10.1107/S1600536814010125

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o647-o648

doi:10.1107/S1600536814010125

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(Z)-1-[(2E)-3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene]-2-[1-(4-hydroxyphenyl)ethylidene]hydrazinium bromide including an unknown solvate

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

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

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 29 April 2014; accepted 5 May 2014; online 10 May 2014)

In the title compound, C₂₃H₂₀N₃OS⁺·Br⁻, the dihydrothiazole ring (r.m.s. deviation = 0.015 Å) is twisted with respect to each of the C- and N-bound phenyl rings and the hydroxybenzene ring, making dihedral angles of 76.0 (2), 71.2 (2) and 9.8 (2)°, respectively. In the crystal, inversion-related molecules are linked by association of the bromide ions with the cations via N—H⋯Br and O—H⋯Br hydrogen-bonding interactions. These molecules run in channels parallel to the a axis through face-to-face π–π stacking interactions between the hydroxybenzene rings [centroid–centroid distances = 3.785 (3) Å] which, in turn, are connected into layers parallel to (110) by weak C—H⋯π interactions. A small region of electron density well removed from the main molecule and appearing disordered over a center of symmetry was removed with PLATON SQUEEZE [Spek (2009 ). Acta Cryst. D65, 148–15] following unsuccessful attempts to model it as plausible solvent molecule. The nature of the solvent was not known and hence, this is not taken into account when calculating M_r and related data.

CCDC reference: 1000895

Related literature

For general medicinal and industrial applications of five-membered S,N-heterocycles thiazolines, see: Abhinit et al. (2009 ). For chemical and diverse medicinal properties of thiazoles, see: Sreedevi et al. (2013 ); Milne (2000 ); De Souza & De Almeida (2003 ); Lednicer et al. (1990 ); Rehman et al. (2005 ); Knadler et al. (1986 ). For a similar structure, see: Mague et al. (2014 ).

Experimental

Crystal data

C₂₃H₂₀N₃OS⁺·Br⁻
M_r = 466.39
Triclinic, $[P \overline 1]$
a = 7.5987 (12) Å
b = 12.3017 (19) Å
c = 13.786 (2) Å
α = 68.0760 (17)°
β = 88.1540 (18)°
γ = 72.6540 (18)°
V = 1136.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.92 mm⁻¹
T = 220 K
0.17 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.56, T_max = 0.80
11044 measured reflections
5146 independent reflections
3398 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.157
S = 1.01
5146 reflections
263 parameters
73 restraints
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯Br1ⁱ	0.83	2.50	3.328 (4)	178
N2—H2⋯Br1ⁱⁱ	0.91	2.88	3.570 (3)	134
C5—H5⋯Cg4ⁱⁱⁱ	0.94	2.76	3.610 (5)	152
Symmetry codes: (i) x-1, y+1, z+1; (ii) -x, -y+1, -z+1; (iii) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supporting information

CCDC reference: 1000895

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814010125/tk5311sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010125/tk5311Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010125/tk5311Isup3.cml

checkCIF report

Structural commentary top

Synthesis of five-membered S,N-heterocycles thiazolines has received intensive interest from chemists and biologists due to their wide spectrum of medicinal and industrial applications (Abhinit et al., 2009). Thiazoles are stable and non-carcinogenic aromatic compounds with relatively small size (Sreedevi et al., 2013). Many biologically active products, such as Bleomycin and Tiazofurin (antineoplastic agents) (Milne, 2000), Ritonavir (anti-HIV drug) (De Souza & De Almeida, 2003), Fanetizole and Meloxicam (anti-inﬂammatory agents) (Lednicer et al., 1990; Rehman et al., 2005), Nizatidine (antiulcer agent) (Knadler et al., 1986) and penicillin (antibiotic) are some examples of thiazole-bearing compounds.

In the title molecule (I), shown in Fig. 1, the 5-membered heterocycle (S1/N1/C1–C3) is planar to within 0.013 (3) Å for N1 and the phenyl rings C4–C9 and C10–C15 make dihedral angles with it of 76.0 (2)° and 71.2 (2)°, respectively. The dihedral angle between the ring C18–C23 and the heterocycle (S1/N1/C1–C3) is 9.8 (2)°. The N1–C3–N2–N3, C3–N2–N3–C18, N2–N3–C16–C18 torsion angles are 173.6 (4), 166.3 (4) and -177.1 (3)°, respectively. All bond lengths and bond angles in (I) are normal and are comparable with those found in a similar structure (Mague et al., 2014).

In the crystal, inversion-related molecules are linked by association of the bromide ions with the cations via N—H···Br and O—H···Br hydrogen bonding interactions (Table 1, Fig. 2). These molecules run in channels parallel to the a axis through the face-to-face π—π stacking interactions [centroid-to-centroid distances = 3.785 (3) Å] between the hydroxylbenzene rings: these are connected into layers parallel to (110) by weak C5—H5···Cg(C18–C23) interactions, Table 1.

Synthesis and crystallization top

The title compound was prepared according to our reported method (Mague et al., 2014). The crude product has been crystallized from ethanol to afford colorless crystals suitable for X-ray diffraction (m.p.: 533 – 535 K).

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H= 0.94–0.97 Å, N–H = 0.91 Å and O–H = 0.83 Å, and with U_iso(H)= 1.2U_eq(C,N) and 1.5 U_eq(O). A small region of electron density well–removed from the main molecule and appearing disordered over a center of symmetry was removed with PLATON SQUEEZE following unsuccessful attempts to model it as plausible lattice solvent (Spek, 2009).

Related literature top

For general medicinal and industrial applications of five-membered S,N-heterocycles thiazolines, see: Abhinit et al. (2009). For chemical and diverse medicinal properties of thiazoles, see: Sreedevi et al. (2013); Milne (2000); De Souza & De Almeida (2003); Lednicer et al. (1990); Rehman et al. (2005); Knadler et al. (1986). For a similar structure, see: Mague et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the asymmetric unit with 30% probability displacement ellipsoids.
	Fig. 2. Packing viewed down the a axis and showing O—H···Br interactions.

(Z)-1-[(2E)-3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene]-2-[1-(4-hydroxyphenyl)ethylidene]hydrazinium bromide top

Crystal data top

C₂₃H₂₀N₃OS⁺·Br⁻	Z = 2
M_r = 466.39	F(000) = 476
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5987 (12) Å	Cell parameters from 4151 reflections
b = 12.3017 (19) Å	θ = 2.8–26.7°
c = 13.786 (2) Å	µ = 1.92 mm⁻¹
α = 68.0760 (17)°	T = 220 K
β = 88.1540 (18)°	Block, colourless
γ = 72.6540 (18)°	0.17 × 0.17 × 0.12 mm
V = 1136.6 (3) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	5146 independent reflections
Radiation source: fine-focus sealed tube	3398 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 8.3660 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −15→15
T_min = 0.56, T_max = 0.80	l = −17→17
11044 measured reflections

Refinement top

Refinement on F²	73 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.157	w = 1/[σ²(F_o²) + (0.0867P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5146 reflections	Δρ_max = 1.09 e Å⁻³
263 parameters	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₂₃H₂₀N₃OS⁺·Br⁻	γ = 72.6540 (18)°
M_r = 466.39	V = 1136.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.5987 (12) Å	Mo Kα radiation
b = 12.3017 (19) Å	µ = 1.92 mm⁻¹
c = 13.786 (2) Å	T = 220 K
α = 68.0760 (17)°	0.17 × 0.17 × 0.12 mm
β = 88.1540 (18)°

Data collection top

Bruker SMART APEX CCD diffractometer	5146 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	3398 reflections with I > 2σ(I)
T_min = 0.56, T_max = 0.80	R_int = 0.042
11044 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	73 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.01	Δρ_max = 1.09 e Å⁻³
5146 reflections	Δρ_min = −0.48 e Å⁻³
263 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 Å. That attached to oxygen was placed in an idealized position and the C—C—O—H torsion angle refined (AFIX 147)·All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. A small region of electron density well removed from the main molecule and appearing disordered over a center of symmetry was removed with PLATON SQUEEZE following unsuccessful attempts to model it as plausible lattice solvent (Spek, 2014).

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

	x	y	z	U_iso*/U_eq
S1	0.24831 (13)	0.51039 (10)	0.99502 (8)	0.0418 (3)
O1	−0.1920 (4)	1.0140 (3)	1.2638 (2)	0.0599 (11)
N1	0.1776 (4)	0.5582 (3)	0.8008 (2)	0.0376 (10)
N2	−0.0083 (4)	0.7072 (3)	0.8605 (2)	0.0427 (11)
N3	−0.0284 (5)	0.7434 (3)	0.9459 (2)	0.0434 (11)
C1	0.3784 (5)	0.4108 (4)	0.9384 (3)	0.0433 (12)
C2	0.3282 (5)	0.4476 (4)	0.8368 (3)	0.0399 (12)
C3	0.1253 (5)	0.6024 (4)	0.8761 (3)	0.0393 (12)
C4	0.4141 (5)	0.3930 (4)	0.7614 (3)	0.0398 (12)
C5	0.3820 (6)	0.2897 (4)	0.7589 (3)	0.0480 (16)
C6	0.4610 (6)	0.2396 (4)	0.6870 (4)	0.0510 (16)
C7	0.5711 (7)	0.2920 (5)	0.6183 (4)	0.0604 (17)
C8	0.6055 (8)	0.3930 (5)	0.6209 (5)	0.085 (3)
C9	0.5280 (7)	0.4447 (5)	0.6915 (4)	0.070 (2)
C10	0.0904 (5)	0.6216 (4)	0.6942 (3)	0.0389 (12)
C11	−0.0203 (6)	0.5700 (4)	0.6591 (4)	0.0543 (17)
C12	−0.1016 (7)	0.6310 (5)	0.5574 (4)	0.0689 (19)
C13	−0.0764 (6)	0.7396 (5)	0.4938 (4)	0.0608 (18)
C14	0.0333 (6)	0.7896 (5)	0.5299 (4)	0.0576 (17)
C15	0.1188 (6)	0.7291 (4)	0.6313 (3)	0.0495 (14)
C16	−0.1282 (5)	0.8544 (4)	0.9258 (3)	0.0380 (12)
C17	−0.2232 (6)	0.9401 (4)	0.8202 (3)	0.0478 (14)
C18	−0.1445 (5)	0.8977 (4)	1.0145 (3)	0.0388 (12)
C19	−0.0230 (6)	0.8316 (4)	1.1041 (3)	0.0443 (12)
C20	−0.0409 (6)	0.8719 (4)	1.1875 (3)	0.0480 (16)
C21	−0.1813 (6)	0.9791 (4)	1.1794 (3)	0.0446 (14)
C22	−0.2998 (6)	1.0452 (4)	1.0906 (3)	0.0470 (14)
C23	−0.2808 (6)	1.0045 (4)	1.0093 (3)	0.0451 (14)
Br1	0.46263 (6)	0.27288 (4)	0.21975 (3)	0.0504 (2)
H1	0.47420	0.33840	0.97570	0.0520*
H1O	−0.27870	1.07870	1.25100	0.0900*
H2	−0.09160	0.73360	0.80430	0.0510*
H5	0.30560	0.25280	0.80650	0.0570*
H6	0.43800	0.16900	0.68600	0.0620*
H7	0.62360	0.25870	0.56900	0.0730*
H8	0.68370	0.42830	0.57370	0.1020*
H9	0.55280	0.51490	0.69200	0.0830*
H11	−0.03950	0.49580	0.70320	0.0650*
H12	−0.17560	0.59700	0.53150	0.0830*
H13	−0.13440	0.78040	0.42500	0.0730*
H14	0.05050	0.86450	0.48600	0.0690*
H15	0.19550	0.76220	0.65630	0.0590*
H17A	−0.26820	1.02330	0.81860	0.0720*
H17B	−0.32660	0.91560	0.80600	0.0720*
H17C	−0.13670	0.93690	0.76730	0.0720*
H19	0.07160	0.75970	1.10900	0.0530*
H20	0.04110	0.82700	1.24860	0.0580*
H22	−0.39340	1.11780	1.08500	0.0570*
H23	−0.36270	1.05060	0.94830	0.0540*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0397 (6)	0.0478 (6)	0.0404 (5)	−0.0129 (5)	0.0012 (4)	−0.0197 (5)
O1	0.068 (2)	0.069 (2)	0.0568 (19)	−0.0195 (17)	0.0135 (15)	−0.0413 (17)
N1	0.0332 (17)	0.0438 (19)	0.0401 (17)	−0.0070 (14)	0.0016 (13)	−0.0244 (15)
N2	0.0413 (19)	0.050 (2)	0.0405 (18)	−0.0047 (15)	−0.0006 (14)	−0.0282 (16)
N3	0.050 (2)	0.050 (2)	0.0363 (17)	−0.0139 (17)	0.0061 (14)	−0.0244 (16)
C1	0.038 (2)	0.045 (2)	0.047 (2)	−0.0093 (18)	0.0020 (17)	−0.0202 (19)
C2	0.036 (2)	0.040 (2)	0.046 (2)	−0.0114 (17)	0.0024 (16)	−0.0192 (18)
C3	0.036 (2)	0.044 (2)	0.044 (2)	−0.0112 (17)	0.0021 (16)	−0.0243 (18)
C4	0.035 (2)	0.036 (2)	0.049 (2)	−0.0077 (17)	0.0045 (16)	−0.0193 (18)
C5	0.047 (2)	0.052 (3)	0.057 (3)	−0.026 (2)	0.0103 (19)	−0.026 (2)
C6	0.049 (3)	0.045 (2)	0.067 (3)	−0.009 (2)	−0.001 (2)	−0.034 (2)
C7	0.059 (3)	0.058 (3)	0.068 (3)	−0.008 (2)	0.018 (2)	−0.037 (3)
C8	0.092 (4)	0.073 (4)	0.114 (5)	−0.043 (3)	0.065 (4)	−0.054 (4)
C9	0.076 (4)	0.059 (3)	0.104 (4)	−0.038 (3)	0.050 (3)	−0.054 (3)
C10	0.033 (2)	0.046 (2)	0.042 (2)	−0.0056 (17)	0.0046 (16)	−0.0266 (18)
C11	0.052 (3)	0.060 (3)	0.055 (3)	−0.020 (2)	0.000 (2)	−0.024 (2)
C12	0.060 (3)	0.090 (4)	0.070 (3)	−0.024 (3)	−0.013 (2)	−0.043 (3)
C13	0.045 (3)	0.085 (4)	0.044 (2)	−0.006 (2)	−0.0011 (19)	−0.026 (2)
C14	0.049 (3)	0.062 (3)	0.050 (3)	−0.011 (2)	0.003 (2)	−0.013 (2)
C15	0.044 (2)	0.060 (3)	0.047 (2)	−0.020 (2)	0.0041 (18)	−0.020 (2)
C16	0.031 (2)	0.043 (2)	0.045 (2)	−0.0111 (17)	0.0097 (16)	−0.0230 (18)
C17	0.051 (3)	0.049 (2)	0.048 (2)	−0.016 (2)	0.0018 (18)	−0.023 (2)
C18	0.038 (2)	0.046 (2)	0.043 (2)	−0.0223 (18)	0.0144 (16)	−0.0223 (18)
C19	0.047 (2)	0.048 (2)	0.048 (2)	−0.0208 (19)	0.0112 (18)	−0.025 (2)
C20	0.050 (3)	0.055 (3)	0.044 (2)	−0.022 (2)	0.0069 (18)	−0.020 (2)
C21	0.049 (2)	0.053 (3)	0.050 (2)	−0.026 (2)	0.0232 (19)	−0.033 (2)
C22	0.043 (2)	0.055 (3)	0.052 (2)	−0.015 (2)	0.0135 (18)	−0.031 (2)
C23	0.041 (2)	0.052 (3)	0.051 (2)	−0.0170 (19)	0.0138 (18)	−0.028 (2)
Br1	0.0562 (3)	0.0514 (3)	0.0488 (3)	−0.0152 (2)	−0.0025 (2)	−0.0252 (2)

Geometric parameters (Å, º) top

S1—C1	1.741 (5)	C16—C18	1.494 (6)
S1—C3	1.710 (4)	C18—C23	1.388 (7)
O1—C21	1.375 (5)	C18—C19	1.384 (6)
O1—H1O	0.8300	C19—C20	1.401 (6)
N1—C3	1.341 (5)	C20—C21	1.396 (7)
N1—C10	1.451 (5)	C21—C22	1.365 (6)
N1—C2	1.418 (6)	C22—C23	1.376 (6)
N2—C3	1.329 (6)	C1—H1	0.9400
N2—N3	1.395 (4)	C5—H5	0.9400
N3—C16	1.277 (6)	C6—H6	0.9400
N2—H2	0.9100	C7—H7	0.9400
C1—C2	1.331 (5)	C8—H8	0.9400
C2—C4	1.474 (6)	C9—H9	0.9400
C4—C9	1.378 (7)	C11—H11	0.9400
C4—C5	1.376 (7)	C12—H12	0.9400
C5—C6	1.386 (7)	C13—H13	0.9400
C6—C7	1.352 (7)	C14—H14	0.9400
C7—C8	1.357 (9)	C15—H15	0.9400
C8—C9	1.379 (9)	C17—H17A	0.9700
C10—C11	1.385 (7)	C17—H17B	0.9700
C10—C15	1.360 (6)	C17—H17C	0.9700
C11—C12	1.380 (7)	C19—H19	0.9400
C12—C13	1.363 (8)	C20—H20	0.9400
C13—C14	1.372 (8)	C22—H22	0.9400
C14—C15	1.387 (6)	C23—H23	0.9400
C16—C17	1.490 (6)

C1—S1—C3	89.3 (2)	O1—C21—C20	116.9 (4)
C21—O1—H1O	109.00	C20—C21—C22	120.5 (4)
C2—N1—C10	125.3 (3)	C21—C22—C23	119.3 (5)
C3—N1—C10	122.2 (4)	C18—C23—C22	122.1 (4)
C2—N1—C3	112.5 (3)	S1—C1—H1	124.00
N3—N2—C3	114.7 (3)	C2—C1—H1	123.00
N2—N3—C16	115.3 (3)	C4—C5—H5	120.00
C3—N2—H2	115.00	C6—C5—H5	120.00
N3—N2—H2	128.00	C5—C6—H6	120.00
S1—C1—C2	113.1 (4)	C7—C6—H6	120.00
N1—C2—C1	111.8 (4)	C6—C7—H7	120.00
N1—C2—C4	119.4 (3)	C8—C7—H7	120.00
C1—C2—C4	128.7 (4)	C7—C8—H8	119.00
S1—C3—N1	113.3 (3)	C9—C8—H8	119.00
N1—C3—N2	123.7 (3)	C4—C9—H9	120.00
S1—C3—N2	123.0 (3)	C8—C9—H9	120.00
C5—C4—C9	118.5 (4)	C10—C11—H11	121.00
C2—C4—C5	120.9 (4)	C12—C11—H11	121.00
C2—C4—C9	120.6 (5)	C11—C12—H12	119.00
C4—C5—C6	120.7 (4)	C13—C12—H12	119.00
C5—C6—C7	120.1 (5)	C12—C13—H13	120.00
C6—C7—C8	119.7 (5)	C14—C13—H13	120.00
C7—C8—C9	121.2 (6)	C13—C14—H14	120.00
C4—C9—C8	119.8 (6)	C15—C14—H14	120.00
C11—C10—C15	121.6 (4)	C10—C15—H15	120.00
N1—C10—C11	118.6 (4)	C14—C15—H15	120.00
N1—C10—C15	119.8 (4)	C16—C17—H17A	109.00
C10—C11—C12	117.9 (5)	C16—C17—H17B	109.00
C11—C12—C13	121.2 (5)	C16—C17—H17C	109.00
C12—C13—C14	120.1 (5)	H17A—C17—H17B	110.00
C13—C14—C15	119.8 (5)	H17A—C17—H17C	110.00
C10—C15—C14	119.4 (4)	H17B—C17—H17C	109.00
C17—C16—C18	120.0 (4)	C18—C19—H19	120.00
N3—C16—C18	116.5 (3)	C20—C19—H19	120.00
N3—C16—C17	123.5 (4)	C19—C20—H20	120.00
C16—C18—C19	120.4 (4)	C21—C20—H20	120.00
C16—C18—C23	121.1 (4)	C21—C22—H22	120.00
C19—C18—C23	118.5 (4)	C23—C22—H22	120.00
C18—C19—C20	120.0 (4)	C18—C23—H23	119.00
C19—C20—C21	119.6 (4)	C22—C23—H23	119.00
O1—C21—C22	122.6 (4)

C3—S1—C1—C2	0.0 (4)	C2—C4—C9—C8	−179.3 (5)
C1—S1—C3—N1	1.4 (3)	C5—C4—C9—C8	0.4 (7)
C1—S1—C3—N2	−178.5 (4)	C4—C5—C6—C7	0.1 (7)
C3—N1—C2—C1	2.3 (5)	C5—C6—C7—C8	0.7 (8)
C3—N1—C2—C4	−174.3 (4)	C6—C7—C8—C9	−1.0 (9)
C10—N1—C2—C1	−179.8 (4)	C7—C8—C9—C4	0.4 (9)
C10—N1—C2—C4	3.6 (6)	N1—C10—C11—C12	−179.7 (4)
C2—N1—C3—S1	−2.4 (4)	C15—C10—C11—C12	0.2 (7)
C2—N1—C3—N2	177.5 (4)	N1—C10—C15—C14	−179.4 (4)
C10—N1—C3—S1	179.6 (3)	C11—C10—C15—C14	0.8 (7)
C10—N1—C3—N2	−0.5 (6)	C10—C11—C12—C13	−1.0 (8)
C2—N1—C10—C11	72.5 (5)	C11—C12—C13—C14	0.9 (9)
C2—N1—C10—C15	−107.4 (5)	C12—C13—C14—C15	0.1 (8)
C3—N1—C10—C11	−109.8 (5)	C13—C14—C15—C10	−0.9 (8)
C3—N1—C10—C15	70.3 (5)	N3—C16—C18—C19	15.2 (6)
C3—N2—N3—C16	166.3 (4)	N3—C16—C18—C23	−164.8 (4)
N3—N2—C3—S1	6.3 (5)	C17—C16—C18—C19	−163.8 (4)
N3—N2—C3—N1	−173.6 (4)	C17—C16—C18—C23	16.2 (6)
N2—N3—C16—C17	1.9 (6)	C16—C18—C19—C20	−179.1 (4)
N2—N3—C16—C18	−177.1 (3)	C23—C18—C19—C20	0.9 (7)
S1—C1—C2—N1	−1.3 (5)	C16—C18—C23—C22	179.2 (4)
S1—C1—C2—C4	175.0 (4)	C19—C18—C23—C22	−0.9 (7)
N1—C2—C4—C5	−105.2 (5)	C18—C19—C20—C21	−0.2 (7)
N1—C2—C4—C9	74.5 (6)	C19—C20—C21—O1	180.0 (4)
C1—C2—C4—C5	78.8 (6)	C19—C20—C21—C22	−0.6 (7)
C1—C2—C4—C9	−101.5 (6)	O1—C21—C22—C23	−179.9 (4)
C2—C4—C5—C6	179.1 (4)	C20—C21—C22—C23	0.6 (7)
C9—C4—C5—C6	−0.6 (7)	C21—C22—C23—C18	0.1 (7)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C18–C23 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Br1ⁱ	0.83	2.50	3.328 (4)	178
N2—H2···Br1ⁱⁱ	0.91	2.88	3.570 (3)	134
C5—H5···Cg4ⁱⁱⁱ	0.94	2.76	3.610 (5)	152

Symmetry codes: (i) x−1, y+1, z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C18–C23 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Br1ⁱ	0.83	2.50	3.328 (4)	178
N2—H2···Br1ⁱⁱ	0.91	2.88	3.570 (3)	134
C5—H5···Cg4ⁱⁱⁱ	0.94	2.76	3.610 (5)	152

Symmetry codes: (i) x−1, y+1, z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2.

Acknowledgements

The support of Tulane University for the Tulane Crystallography Laboratory is gratefully acknowledged.

References

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Volume 70| Part 6| June 2014| Pages o647-o648

doi:10.1107/S1600536814010125

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

(Z)-1-[(2E)-3,4-Di­phenyl-2,3-di­hydro-1,3-thia­zol-2-yl­­idene]-2-[1-(4-hy­dr­oxy­phen­yl)ethyl­­idene]hydrazinium bromide including an unknown solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-1-[(2E)-3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene]-2-[1-(4-hydroxyphenyl)ethylidene]hydrazinium bromide including an unknown solvate