(2E)-4-(4-Bromo­phen­yl)-2-{2-[(1E)-cyclo­pentyl­idene]hydrazin-1-yl­idene}-3-phenyl-2,3-di­hydro-1,3-thia­zole

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

doi:10.1107/S1600536814010897

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o669

doi:10.1107/S1600536814010897

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(2E)-4-(4-Bromophenyl)-2-{2-[(1E)-cyclopentylidene]hydrazin-1-ylidene}-3-phenyl-2,3-dihydro-1,3-thiazole

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

(Received 9 May 2014; accepted 12 May 2014; online 17 May 2014)

In the title compound, C₂₀H₁₈BrN₃S, the cyclopentane ring adopts a half-chair conformation. The 4-bromophenyl and phenyl rings make dihedral angles of 34.6 (1) and 68.52 (6)°, respectively, with the dihydrothiazole ring. In the crystal, the molecules pack in sheets approximately parallel to (101) which are formed by weak C—H⋯Br interactions

CCDC reference: 1002511

Related literature

For variuos medicinal applications of thiazole scaffold compounds, see: Mahajan et al. (2008 ); Abbs et al. (2008 ); Chowki et al. (2008 ); Karabasanagouda et al. (2008 ); Basavaraja et al. (2008 ); Bhusari et al. (2000 ); Basawaraj et al. (2005 ). For similar structures, see: Akkurt et al. (2014 ); Mague et al. (2014 ); Mohamed et al. (2013 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₁₈BrN₃S
M_r = 412.34
Monoclinic, P 2₁ /c
a = 12.5079 (3) Å
b = 5.5728 (1) Å
c = 25.3761 (6) Å
β = 96.8480 (11)°
V = 1756.20 (7) Å³
Z = 4
Cu Kα radiation
μ = 4.35 mm⁻¹
T = 100 K
0.10 × 0.08 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.80, T_max = 0.92
12815 measured reflections
3409 independent reflections
2960 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.072
S = 1.06
3409 reflections
230 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯Br1ⁱ	0.99	3.03	3.828 (2)	138
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: 1002511

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814010897/qm2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010897/qm2107Isup2.hkl

checkCIF report

Comment top

The anti-microbial activities of substituted thiazoles are well established because they possess the (S—C=N) toxophoric unit (Mahajan et al., 2008). Thiazoles were reported to possess anti-cancer (Abbs et al., 2008), anti-tubercular (Chowki et al., 2008), anti-inflammatory (Karabasanagouda et al., 2008), analgesic (Basavaraja et al., 2008) anthelmintic (Bhusari et al., 2000) and diuretic (Basawaraj et al., 2005) activities. Based on these facts and as part of our on-going study we herein report the synthesis and crystal structure of the title compound.

In the title compound (I, Fig. 1), the cyclopentane ring (C16–C20) adopts a half-chair conformation with puckering parameters of Q(2) = 0.375 (3) Å, ϕ (2) = 270.2 (4) ° (Cremer & Pople, 1975). The dihydrothiazole ring (S1/N1/C7–C9) is essentially planar [max. deviations = -0.002 (2) Å for C8 and C9] and it makes dihedral angles of 34.6 (1) and 68.52 (6)%, respectively, with the 4-bromophenyl (C1–C6) and (C10–C15) phenyl rings. All bond lengths and angles in (I) are normal and comparable with those reported for similar structures (Mohamed et al., 2013; Mague et al., 2014; Akkurt et al., 2014).

In the crystal, the molecules of (I) pack in sheets approximately parallel to (101) which are formed by weak C—H···Br interactions (Table 1, Fig. 2).

Related literature top

For variuos medicinal applications of thiazole scaffold compounds, see: Mahajan et al. (2008); Abbs et al. (2008); Chowki et al. (2008); Karabasanagouda et al. (2008); Basavaraja et al. (2008); Bhusari et al. (2000); Basawaraj et al. (2005). For similar structures, see: Akkurt et al. (2014); Mague et al. (2014); Mohamed et al. (2013). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of 1 mmol (233 mg) of cyclopentan-1-one N-phenylthiosemicarbazone and 1 mmol (278 mg) of 2-bromo-1-(4-bromophenyl)ethanone in 30 ml e thanol was stirred and refluxed at 350 K. The reaction was monitored by TLC until completion. On cooling, a solid yellow product precipitated which was filtered off and recrystallized from ethanol to furnish yellow crystals, suitable for X-ray diffraction.

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 50% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. Packing viewed down the b axis with the C—H···Br interactions shown as dotted lines.

(2E)-4-(4-Bromophenyl)-2-{2-[(1E)-cyclopentylidene]hydrazin-1-ylidene}-3-phenyl-2,3-dihydro-1,3-thiazole top

Crystal data top

C₂₀H₁₈BrN₃S	F(000) = 840
M_r = 412.34	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 12.5079 (3) Å	Cell parameters from 8908 reflections
b = 5.5728 (1) Å	θ = 3.5–72.3°
c = 25.3761 (6) Å	µ = 4.35 mm⁻¹
β = 96.8480 (11)°	T = 100 K
V = 1756.20 (7) Å³	Plate, yellow
Z = 4	0.10 × 0.08 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3409 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2960 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 3.5°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −6→6
T_min = 0.80, T_max = 0.92	l = −31→29
12815 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0367P)² + 0.942P] where P = (F_o² + 2F_c²)/3
3409 reflections	(Δ/σ)_max = 0.004
230 parameters	Δρ_max = 0.89 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₁₈BrN₃S	V = 1756.20 (7) Å³
M_r = 412.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.5079 (3) Å	µ = 4.35 mm⁻¹
b = 5.5728 (1) Å	T = 100 K
c = 25.3761 (6) Å	0.10 × 0.08 × 0.02 mm
β = 96.8480 (11)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3409 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2960 reflections with I > 2σ(I)
T_min = 0.80, T_max = 0.92	R_int = 0.033
12815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	Δρ_max = 0.89 e Å⁻³
3409 reflections	Δρ_min = −0.26 e Å⁻³
230 parameters

Special details top

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 were placed in

calculated positions (C—H = 0.95 - 0.99 Å) and included as riding

contributions with isotropic displacement parameters 1.2 times those

of the attached carbon atoms. At the conclusion of refinement with all

atoms at unit occupancy, the largest difference peak appeared in the

vicinity of Br1. Refinement of this as a second component of a disorder

of Br1 led to improvement in the results and a more realistic value for

U(iso) for Br1. The geometry associated with the minor component (Br1A)

suggests that there is a small amount of "whole molecule" disorder but

since the refined occupancy of Br1A is only 0.02, there is not enough

information from the final difference map to reliably position the

remainder of the minor component.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.85490 (2)	−0.31880 (7)	0.43991 (2)	0.02218 (11)	0.982 (1)
Br1A	0.8563 (12)	−0.201 (4)	0.4313 (4)	0.02218 (11)	0.0182 (11)
S1	0.94129 (4)	0.58669 (10)	0.71625 (2)	0.01954 (13)
N1	0.77696 (15)	0.4902 (3)	0.64754 (7)	0.0186 (4)
N2	0.74281 (16)	0.7923 (4)	0.70865 (8)	0.0219 (4)
N3	0.80239 (15)	0.9247 (4)	0.75009 (7)	0.0219 (4)
C1	0.85169 (18)	−0.1224 (4)	0.50103 (9)	0.0188 (4)
C2	0.91130 (18)	−0.1876 (4)	0.54836 (9)	0.0206 (5)
H2	0.9528	−0.3308	0.5507	0.025*
C3	0.90938 (18)	−0.0397 (4)	0.59242 (9)	0.0192 (4)
H3	0.9493	−0.0842	0.6252	0.023*
C4	0.84970 (17)	0.1732 (4)	0.58934 (8)	0.0173 (4)
C5	0.79033 (19)	0.2330 (4)	0.54094 (9)	0.0197 (5)
H5	0.7492	0.3767	0.5382	0.024*
C6	0.79050 (19)	0.0856 (4)	0.49681 (9)	0.0209 (5)
H6	0.7492	0.1267	0.4642	0.025*
C7	0.86033 (18)	0.3344 (4)	0.63585 (9)	0.0180 (4)
C8	0.95119 (19)	0.3650 (4)	0.66889 (9)	0.0194 (5)
H8	1.0148	0.2744	0.6666	0.023*
C9	0.80684 (18)	0.6404 (4)	0.69039 (8)	0.0183 (4)
C10	0.66773 (18)	0.4827 (4)	0.62245 (8)	0.0187 (4)
C11	0.6062 (2)	0.2806 (4)	0.62887 (9)	0.0225 (5)
H11	0.6344	0.1517	0.6508	0.027*
C12	0.5018 (2)	0.2708 (4)	0.60235 (10)	0.0265 (5)
H12	0.4580	0.1343	0.6065	0.032*
C13	0.46162 (19)	0.4581 (5)	0.57017 (10)	0.0278 (5)
H13	0.3908	0.4490	0.5520	0.033*
C14	0.5245 (2)	0.6597 (4)	0.56423 (9)	0.0254 (5)
H14	0.4968	0.7879	0.5420	0.030*
C15	0.62813 (19)	0.6735 (4)	0.59085 (9)	0.0219 (5)
H15	0.6712	0.8117	0.5874	0.026*
C16	0.74531 (18)	1.0603 (4)	0.77618 (9)	0.0202 (5)
C17	0.79575 (19)	1.2288 (4)	0.81892 (9)	0.0211 (5)
H17A	0.8308	1.3662	0.8032	0.025*
H17B	0.8499	1.1441	0.8439	0.025*
C18	0.70068 (19)	1.3126 (5)	0.84697 (10)	0.0270 (5)
H18A	0.7132	1.4763	0.8616	0.032*
H18B	0.6882	1.2020	0.8762	0.032*
C19	0.6054 (2)	1.3094 (5)	0.80314 (10)	0.0282 (5)
H19A	0.6050	1.4549	0.7807	0.034*
H19B	0.5363	1.2994	0.8184	0.034*
C20	0.62414 (19)	1.0838 (5)	0.77104 (9)	0.0248 (5)
H20A	0.5911	0.9414	0.7859	0.030*
H20B	0.5938	1.1032	0.7334	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02681 (14)	0.0192 (2)	0.02079 (13)	0.00088 (11)	0.00395 (9)	−0.00472 (11)
Br1A	0.02681 (14)	0.0192 (2)	0.02079 (13)	0.00088 (11)	0.00395 (9)	−0.00472 (11)
S1	0.0204 (3)	0.0212 (3)	0.0163 (3)	0.0003 (2)	−0.0011 (2)	−0.00170 (19)
N1	0.0182 (9)	0.0184 (9)	0.0186 (9)	0.0008 (7)	0.0001 (7)	−0.0038 (7)
N2	0.0215 (10)	0.0251 (10)	0.0185 (9)	0.0000 (8)	−0.0002 (8)	−0.0061 (8)
N3	0.0217 (10)	0.0249 (10)	0.0182 (9)	−0.0002 (8)	−0.0008 (8)	−0.0037 (8)
C1	0.0206 (11)	0.0158 (10)	0.0205 (11)	−0.0037 (9)	0.0044 (9)	−0.0035 (8)
C2	0.0203 (11)	0.0176 (10)	0.0240 (11)	0.0003 (9)	0.0029 (9)	0.0018 (9)
C3	0.0193 (11)	0.0187 (10)	0.0195 (11)	0.0000 (9)	0.0015 (9)	0.0034 (8)
C4	0.0168 (10)	0.0182 (10)	0.0167 (10)	−0.0021 (9)	0.0017 (8)	0.0008 (8)
C5	0.0225 (11)	0.0167 (10)	0.0198 (11)	0.0035 (9)	0.0017 (9)	0.0004 (8)
C6	0.0237 (12)	0.0210 (11)	0.0172 (11)	0.0020 (9)	−0.0005 (9)	0.0007 (8)
C7	0.0207 (11)	0.0160 (10)	0.0173 (10)	0.0006 (9)	0.0027 (8)	0.0021 (8)
C8	0.0221 (11)	0.0181 (10)	0.0179 (11)	0.0011 (9)	0.0020 (9)	−0.0007 (8)
C9	0.0201 (11)	0.0183 (10)	0.0157 (10)	−0.0020 (9)	−0.0012 (9)	0.0006 (8)
C10	0.0197 (11)	0.0194 (11)	0.0171 (10)	−0.0006 (9)	0.0028 (9)	−0.0041 (8)
C11	0.0264 (12)	0.0206 (11)	0.0212 (11)	−0.0027 (10)	0.0059 (9)	−0.0005 (9)
C12	0.0235 (12)	0.0260 (12)	0.0313 (13)	−0.0069 (10)	0.0089 (10)	−0.0064 (10)
C13	0.0181 (11)	0.0361 (14)	0.0286 (13)	0.0007 (11)	0.0001 (10)	−0.0095 (10)
C14	0.0250 (12)	0.0270 (12)	0.0228 (11)	0.0070 (10)	−0.0022 (10)	−0.0020 (9)
C15	0.0226 (12)	0.0196 (11)	0.0236 (11)	−0.0012 (9)	0.0028 (9)	−0.0022 (9)
C16	0.0217 (11)	0.0207 (11)	0.0176 (11)	−0.0015 (9)	0.0002 (9)	−0.0004 (8)
C17	0.0220 (11)	0.0236 (11)	0.0174 (11)	−0.0024 (9)	0.0015 (9)	−0.0029 (8)
C18	0.0245 (12)	0.0329 (13)	0.0233 (12)	0.0004 (11)	0.0024 (10)	−0.0082 (10)
C19	0.0240 (12)	0.0339 (13)	0.0264 (12)	0.0056 (11)	0.0017 (10)	−0.0062 (10)
C20	0.0221 (12)	0.0299 (13)	0.0222 (11)	−0.0009 (10)	0.0014 (9)	−0.0056 (9)

Geometric parameters (Å, º) top

Br1—C1	1.903 (2)	C10—C15	1.387 (3)
Br1A—C1	1.830 (8)	C11—C12	1.397 (4)
S1—C8	1.738 (2)	C11—H11	0.9500
S1—C9	1.756 (2)	C12—C13	1.382 (4)
N1—C9	1.388 (3)	C12—H12	0.9500
N1—C7	1.415 (3)	C13—C14	1.390 (4)
N1—C10	1.437 (3)	C13—H13	0.9500
N2—C9	1.289 (3)	C14—C15	1.390 (3)
N2—N3	1.421 (3)	C14—H14	0.9500
N3—C16	1.277 (3)	C15—H15	0.9500
C1—C2	1.385 (3)	C16—C20	1.511 (3)
C1—C6	1.386 (3)	C16—C17	1.514 (3)
C2—C3	1.391 (3)	C17—C18	1.530 (3)
C2—H2	0.9500	C17—H17A	0.9900
C3—C4	1.399 (3)	C17—H17B	0.9900
C3—H3	0.9500	C18—C19	1.530 (3)
C4—C5	1.398 (3)	C18—H18A	0.9900
C4—C7	1.476 (3)	C18—H18B	0.9900
C5—C6	1.389 (3)	C19—C20	1.531 (3)
C5—H5	0.9500	C19—H19A	0.9900
C6—H6	0.9500	C19—H19B	0.9900
C7—C8	1.340 (3)	C20—H20A	0.9900
C8—H8	0.9500	C20—H20B	0.9900
C10—C11	1.384 (3)

C8—S1—C9	90.38 (11)	C12—C11—H11	120.8
C9—N1—C7	113.44 (18)	C13—C12—C11	120.5 (2)
C9—N1—C10	121.16 (18)	C13—C12—H12	119.7
C7—N1—C10	125.08 (18)	C11—C12—H12	119.7
C9—N2—N3	108.28 (19)	C12—C13—C14	120.2 (2)
C16—N3—N2	114.49 (19)	C12—C13—H13	119.9
C2—C1—C6	121.5 (2)	C14—C13—H13	119.9
C2—C1—Br1A	134.4 (6)	C15—C14—C13	119.9 (2)
C6—C1—Br1A	102.0 (7)	C15—C14—H14	120.0
C2—C1—Br1	119.64 (17)	C13—C14—H14	120.0
C6—C1—Br1	118.90 (17)	C10—C15—C14	119.1 (2)
C1—C2—C3	118.9 (2)	C10—C15—H15	120.4
C1—C2—H2	120.6	C14—C15—H15	120.4
C3—C2—H2	120.6	N3—C16—C20	128.6 (2)
C2—C3—C4	121.2 (2)	N3—C16—C17	121.8 (2)
C2—C3—H3	119.4	C20—C16—C17	109.62 (19)
C4—C3—H3	119.4	C16—C17—C18	104.01 (19)
C5—C4—C3	118.4 (2)	C16—C17—H17A	111.0
C5—C4—C7	123.0 (2)	C18—C17—H17A	111.0
C3—C4—C7	118.35 (19)	C16—C17—H17B	111.0
C6—C5—C4	121.0 (2)	C18—C17—H17B	111.0
C6—C5—H5	119.5	H17A—C17—H17B	109.0
C4—C5—H5	119.5	C17—C18—C19	103.86 (19)
C1—C6—C5	119.1 (2)	C17—C18—H18A	111.0
C1—C6—H6	120.5	C19—C18—H18A	111.0
C5—C6—H6	120.5	C17—C18—H18B	111.0
C8—C7—N1	112.5 (2)	C19—C18—H18B	111.0
C8—C7—C4	124.5 (2)	H18A—C18—H18B	109.0
N1—C7—C4	122.84 (19)	C18—C19—C20	103.9 (2)
C7—C8—S1	113.45 (17)	C18—C19—H19A	111.0
C7—C8—H8	123.3	C20—C19—H19A	111.0
S1—C8—H8	123.3	C18—C19—H19B	111.0
N2—C9—N1	123.8 (2)	C20—C19—H19B	111.0
N2—C9—S1	125.86 (17)	H19A—C19—H19B	109.0
N1—C9—S1	110.27 (16)	C16—C20—C19	103.95 (19)
C11—C10—C15	121.8 (2)	C16—C20—H20A	111.0
C11—C10—N1	118.9 (2)	C19—C20—H20A	111.0
C15—C10—N1	119.3 (2)	C16—C20—H20B	111.0
C10—C11—C12	118.4 (2)	C19—C20—H20B	111.0
C10—C11—H11	120.8	H20A—C20—H20B	109.0

C9—N2—N3—C16	−171.4 (2)	C10—N1—C9—N2	−4.5 (3)
C6—C1—C2—C3	−0.1 (3)	C7—N1—C9—S1	0.2 (2)
Br1A—C1—C2—C3	159.7 (10)	C10—N1—C9—S1	174.06 (16)
Br1—C1—C2—C3	178.96 (16)	C8—S1—C9—N2	178.2 (2)
C1—C2—C3—C4	−0.8 (3)	C8—S1—C9—N1	−0.31 (17)
C2—C3—C4—C5	1.0 (3)	C9—N1—C10—C11	−109.5 (2)
C2—C3—C4—C7	−173.6 (2)	C7—N1—C10—C11	63.6 (3)
C3—C4—C5—C6	−0.2 (3)	C9—N1—C10—C15	73.0 (3)
C7—C4—C5—C6	174.1 (2)	C7—N1—C10—C15	−113.9 (2)
C2—C1—C6—C5	0.9 (3)	C15—C10—C11—C12	0.3 (3)
Br1A—C1—C6—C5	−164.5 (6)	N1—C10—C11—C12	−177.2 (2)
Br1—C1—C6—C5	−178.20 (17)	C10—C11—C12—C13	0.6 (3)
C4—C5—C6—C1	−0.7 (3)	C11—C12—C13—C14	−0.6 (4)
C9—N1—C7—C8	0.0 (3)	C12—C13—C14—C15	−0.2 (4)
C10—N1—C7—C8	−173.5 (2)	C11—C10—C15—C14	−1.1 (3)
C9—N1—C7—C4	−174.9 (2)	N1—C10—C15—C14	176.4 (2)
C10—N1—C7—C4	11.6 (3)	C13—C14—C15—C10	1.0 (3)
C5—C4—C7—C8	−140.5 (2)	N2—N3—C16—C20	4.6 (3)
C3—C4—C7—C8	33.8 (3)	N2—N3—C16—C17	−175.20 (19)
C5—C4—C7—N1	33.8 (3)	N3—C16—C17—C18	−168.4 (2)
C3—C4—C7—N1	−151.9 (2)	C20—C16—C17—C18	11.8 (3)
N1—C7—C8—S1	−0.3 (2)	C16—C17—C18—C19	−31.0 (2)
C4—C7—C8—S1	174.50 (17)	C17—C18—C19—C20	38.9 (3)
C9—S1—C8—C7	0.35 (18)	N3—C16—C20—C19	−167.8 (2)
N3—N2—C9—N1	−176.3 (2)	C17—C16—C20—C19	12.1 (3)
N3—N2—C9—S1	5.4 (3)	C18—C19—C20—C16	−31.2 (2)
C7—N1—C9—N2	−178.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···Br1ⁱ	0.99	3.03	3.828 (2)	138

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···Br1ⁱ	0.99	3.03	3.828 (2)	138

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged.

References

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Volume 70| Part 6| June 2014| Page o669

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

(2E)-4-(4-Bromo­phen­yl)-2-{2-[(1E)-cyclo­pentyl­­idene]hydrazin-1-yl­­idene}-3-phenyl-2,3-di­hydro-1,3-thia­zole

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Experimental

Crystal data

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Refinement

Supporting information

Acknowledgements

References

organic compounds

(2E)-4-(4-Bromophenyl)-2-{2-[(1E)-cyclopentylidene]hydrazin-1-ylidene}-3-phenyl-2,3-dihydro-1,3-thiazole