(2E)-4-(4-Bromo-phen-yl)-2-{2-[(1E)-cyclo-pentyl-idene]hydrazin-1-yl-idene}-3-phenyl-2,3-di-hydro-1,3-thia-zole.

In the title compound, C20H18BrN3S, the cyclo-pentane ring adopts a half-chair conformation. The 4-bromo-phenyl and phenyl rings make dihedral angles of 34.6 (1) and 68.52 (6)°, respectively, with the di-hydro-thia-zole ring. In the crystal, the mol-ecules pack in sheets approximately parallel to (101) which are formed by weak C-H⋯Br inter-actions.

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 = 412.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.06

3409 reflections

230 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −0.26 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/S1600536814010897/qm2107sup1.cif

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

CCDC reference: 1002511

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

C20H18BrN3S	F(000) = 840
Mr = 412.34	Dx = 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

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	Rint = 0.033
Detector resolution: 10.4167 pixels mm-1	θmax = 72.3°, θmin = 3.5°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −6→6
Tmin = 0.80, Tmax = 0.92	l = −31→29
12815 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0367P)2 + 0.942P] where P = (Fo2 + 2Fc2)/3
3409 reflections	(Δ/σ)max = 0.004
230 parameters	Δρmax = 0.89 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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 incalculated positions (C—H = 0.95 - 0.99 Å) and included as ridingcontributions with isotropic displacement parameters 1.2 times thoseof the attached carbon atoms. At the conclusion of refinement with allatoms at unit occupancy, the largest difference peak appeared in thevicinity of Br1. Refinement of this as a second component of a disorderof Br1 led to improvement in the results and a more realistic value forU(iso) for Br1. The geometry associated with the minor component (Br1A)suggests that there is a small amount of "whole molecule" disorder butsince the refined occupancy of Br1A is only 0.02, there is not enoughinformation from the final difference map to reliably position theremainder of the minor component.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) .