(E)-1-(2,5-Dichloro-thio-phen-3-yl)ethan-one [8-(trifluoro-meth-yl)quinolin-4-yl]hydrazone.

In the title compound, C(16)H(10)Cl(2)F(3)N(3)S, the dihedral angle between the quinoline and thio-phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio-phene ring takes part in weak π-π stacking inter-actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and inter-planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of mol-ecules in an alternating head-to-tail arrangement, with two π-π stacking contacts between each adjacent pair.

Related literature

For related structures derived from 4-hydrazinyl-8-(trifluoro­meth­yl)quinoline and background to n class="Chemical">Schiff bases, see; Jasinski et al. (2010 ▶); Dutkiewicz et al. (2010 ▶).

Experimental

Crystal data

C16H10Cl2F3N3S

M = 404.23

Monoclinic,

a = 7.687 (2) Å

b = 14.392 (5) Å

c = 14.360 (5) Å

β = 95.053 (9)°

V = 1582.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 73 K

0.10 × 0.10 × 0.10 mm

Data collection

Rigaku Mercury CCD diffractometer

9805 measured reflections

2897 independent reflections

2369 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.128

S = 1.06

2897 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005673/kp2384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005673/kp2384Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005673/kp2384Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H10Cl2F3N3S	F(000) = 816
Mr = 404.23	Dx = 1.697 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4944 reflections
a = 7.687 (2) Å	θ = 2.0–28.5°
b = 14.392 (5) Å	µ = 0.58 mm−1
c = 14.360 (5) Å	T = 73 K
β = 95.053 (9)°	Prism, colourless
V = 1582.5 (9) Å3	0.10 × 0.10 × 0.10 mm
Z = 4

Rigaku Mercury CCD diffractometer	2369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
Graphite monochromator	θmax = 25.4°, θmin = 2.0°
ω scans	h = −8→9
9805 measured reflections	k = −17→13
2897 independent reflections	l = −17→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.0123P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2897 reflections	Δρmax = 0.35 e Å−3
231 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1	0.4410 (3)	0.25700 (19)	0.39915 (18)	0.0193 (6)
C2	0.5208 (3)	0.16942 (18)	0.42084 (19)	0.0196 (6)
C3	0.5718 (3)	0.1444 (2)	0.51114 (19)	0.0233 (6)
H3	0.6244	0.0855	0.5241	0.028*
C4	0.5458 (3)	0.20637 (19)	0.58497 (19)	0.0222 (6)
H4	0.5840	0.1896	0.6474	0.027*
C5	0.4662 (3)	0.29017 (19)	0.56742 (18)	0.0212 (6)
H5	0.4475	0.3304	0.6180	0.025*
C6	0.4113 (3)	0.31781 (19)	0.47515 (19)	0.0184 (6)
C7	0.3276 (3)	0.40483 (18)	0.45162 (18)	0.0185 (6)
C8	0.2886 (3)	0.4263 (2)	0.35855 (19)	0.0227 (6)
H8	0.2367	0.4842	0.3407	0.027*
C9	0.3269 (3)	0.3612 (2)	0.29090 (19)	0.0213 (6)
H9	0.2985	0.3779	0.2274	0.026*
C10	0.1600 (3)	0.59983 (19)	0.56281 (18)	0.0187 (6)
C11	0.1918 (3)	0.5794 (2)	0.66590 (19)	0.0241 (6)
H11A	0.1622	0.5145	0.6775	0.036*
H11B	0.1188	0.6203	0.7007	0.036*
H11C	0.3151	0.5902	0.6864	0.036*
C12	0.0773 (3)	0.68922 (19)	0.53327 (18)	0.0181 (6)
C13	0.0493 (3)	0.76274 (19)	0.59770 (19)	0.0210 (6)
H13	0.0760	0.7573	0.6633	0.025*
C14	−0.0183 (3)	0.83985 (18)	0.55647 (19)	0.0203 (6)
C15	0.0230 (3)	0.71698 (18)	0.44394 (18)	0.0201 (6)
C16	0.5511 (3)	0.1035 (2)	0.3424 (2)	0.0260 (7)
N1	0.3989 (3)	0.27860 (16)	0.30701 (15)	0.0210 (5)
N2	0.2884 (3)	0.46492 (16)	0.52193 (17)	0.0218 (5)
H1	0.310 (3)	0.449 (2)	0.578 (2)	0.026*
N3	0.2058 (3)	0.54653 (15)	0.49702 (15)	0.0205 (5)
F1	0.65951 (18)	0.13668 (11)	0.28208 (10)	0.0273 (4)
F2	0.6221 (2)	0.02239 (12)	0.37478 (12)	0.0380 (5)
F3	0.40389 (19)	0.07936 (12)	0.28996 (12)	0.0349 (5)
S1	−0.05583 (8)	0.82904 (5)	0.43743 (5)	0.0231 (2)
Cl1	0.01844 (9)	0.65772 (5)	0.34012 (5)	0.0280 (2)
Cl2	−0.06338 (9)	0.94308 (5)	0.60984 (5)	0.0289 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0184 (12)	0.0234 (16)	0.0161 (14)	−0.0038 (11)	0.0015 (10)	−0.0023 (12)
C2	0.0190 (12)	0.0205 (16)	0.0196 (16)	−0.0017 (11)	0.0034 (11)	−0.0028 (12)
C3	0.0211 (13)	0.0273 (17)	0.0218 (16)	−0.0003 (11)	0.0026 (11)	0.0042 (13)
C4	0.0231 (13)	0.0282 (18)	0.0151 (15)	0.0004 (12)	0.0000 (11)	0.0022 (12)
C5	0.0220 (13)	0.0256 (17)	0.0156 (15)	−0.0015 (12)	0.0000 (11)	−0.0028 (12)
C6	0.0174 (13)	0.0203 (16)	0.0173 (15)	−0.0031 (11)	0.0007 (11)	−0.0022 (11)
C7	0.0165 (12)	0.0216 (16)	0.0173 (15)	−0.0027 (11)	0.0017 (10)	−0.0038 (11)
C8	0.0237 (13)	0.0241 (17)	0.0199 (16)	0.0004 (12)	0.0004 (11)	0.0024 (12)
C9	0.0233 (14)	0.0282 (17)	0.0118 (14)	−0.0020 (12)	−0.0017 (11)	0.0002 (12)
C10	0.0151 (12)	0.0232 (16)	0.0174 (15)	−0.0018 (11)	0.0000 (10)	0.0002 (12)
C11	0.0275 (14)	0.0244 (17)	0.0202 (16)	0.0045 (12)	0.0008 (11)	−0.0006 (12)
C12	0.0172 (12)	0.0201 (15)	0.0166 (15)	−0.0036 (11)	0.0002 (10)	0.0001 (11)
C13	0.0239 (13)	0.0220 (16)	0.0170 (15)	−0.0014 (11)	0.0013 (11)	−0.0005 (12)
C14	0.0249 (14)	0.0184 (16)	0.0178 (15)	−0.0001 (11)	0.0025 (11)	−0.0007 (11)
C15	0.0241 (13)	0.0205 (16)	0.0158 (15)	−0.0029 (11)	0.0019 (11)	−0.0034 (12)
C16	0.0266 (14)	0.0247 (18)	0.0271 (17)	−0.0027 (13)	0.0049 (12)	−0.0022 (13)
N1	0.0237 (11)	0.0243 (14)	0.0148 (12)	−0.0025 (10)	0.0010 (9)	0.0000 (10)
N2	0.0274 (11)	0.0222 (14)	0.0154 (12)	0.0021 (10)	−0.0008 (10)	0.0006 (11)
N3	0.0238 (11)	0.0186 (13)	0.0185 (13)	0.0020 (9)	−0.0007 (9)	−0.0003 (10)
F1	0.0267 (8)	0.0366 (11)	0.0194 (9)	−0.0026 (7)	0.0063 (7)	−0.0057 (7)
F2	0.0598 (11)	0.0226 (10)	0.0330 (11)	0.0107 (8)	0.0116 (9)	−0.0022 (8)
F3	0.0309 (9)	0.0410 (12)	0.0332 (10)	−0.0128 (7)	0.0056 (7)	−0.0185 (8)
S1	0.0268 (4)	0.0227 (5)	0.0193 (4)	0.0011 (3)	−0.0002 (3)	0.0026 (3)
Cl1	0.0410 (4)	0.0286 (5)	0.0140 (4)	0.0020 (3)	−0.0001 (3)	−0.0011 (3)
Cl2	0.0384 (4)	0.0216 (5)	0.0276 (5)	0.0048 (3)	0.0070 (3)	−0.0021 (3)

C1—N1	1.370 (3)	C10—C12	1.481 (4)
C1—C2	1.424 (4)	C10—C11	1.508 (4)
C1—C6	1.433 (4)	C11—H11A	0.9800
C2—C3	1.369 (4)	C11—H11B	0.9800
C2—C16	1.507 (4)	C11—H11C	0.9800
C3—C4	1.413 (4)	C12—C15	1.373 (4)
C3—H3	0.9500	C12—C13	1.434 (4)
C4—C5	1.366 (4)	C13—C14	1.341 (4)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.412 (4)	C14—S1	1.715 (3)
C5—H5	0.9500	C14—Cl2	1.721 (3)
C6—C7	1.435 (4)	C15—Cl1	1.715 (3)
C7—C8	1.379 (4)	C15—S1	1.722 (3)
C7—N2	1.383 (3)	C16—F1	1.342 (3)
C8—C9	1.400 (4)	C16—F3	1.349 (3)
C8—H8	0.9500	C16—F2	1.353 (3)
C9—N1	1.323 (3)	N2—N3	1.368 (3)
C9—H9	0.9500	N2—H1	0.85 (3)
C10—N3	1.290 (3)
N1—C1—C2	118.2 (2)	C10—C11—H11A	109.5
N1—C1—C6	123.9 (3)	C10—C11—H11B	109.5
C2—C1—C6	117.9 (2)	H11A—C11—H11B	109.5
C3—C2—C1	121.5 (2)	C10—C11—H11C	109.5
C3—C2—C16	119.5 (3)	H11A—C11—H11C	109.5
C1—C2—C16	119.1 (2)	H11B—C11—H11C	109.5
C2—C3—C4	119.8 (3)	C15—C12—C13	109.7 (2)
C2—C3—H3	120.1	C15—C12—C10	127.5 (2)
C4—C3—H3	120.1	C13—C12—C10	122.8 (2)
C5—C4—C3	120.6 (3)	C14—C13—C12	113.6 (2)
C5—C4—H4	119.7	C14—C13—H13	123.2
C3—C4—H4	119.7	C12—C13—H13	123.2
C4—C5—C6	120.9 (2)	C13—C14—S1	112.9 (2)
C4—C5—H5	119.5	C13—C14—Cl2	127.1 (2)
C6—C5—H5	119.5	S1—C14—Cl2	119.95 (16)
C5—C6—C1	119.2 (3)	C12—C15—Cl1	130.4 (2)
C5—C6—C7	123.9 (2)	C12—C15—S1	113.6 (2)
C1—C6—C7	116.9 (2)	Cl1—C15—S1	115.99 (15)
C8—C7—N2	121.7 (3)	F1—C16—F3	105.6 (2)
C8—C7—C6	118.6 (2)	F1—C16—F2	105.9 (2)
N2—C7—C6	119.7 (2)	F3—C16—F2	105.3 (2)
C7—C8—C9	118.8 (3)	F1—C16—C2	113.8 (2)
C7—C8—H8	120.6	F3—C16—C2	113.7 (2)
C9—C8—H8	120.6	F2—C16—C2	111.8 (2)
N1—C9—C8	126.2 (3)	C9—N1—C1	115.6 (2)
N1—C9—H9	116.9	N3—N2—C7	118.2 (2)
C8—C9—H9	116.9	N3—N2—H1	122.0 (19)
N3—C10—C12	116.4 (2)	C7—N2—H1	119.7 (19)
N3—C10—C11	124.9 (2)	C10—N3—N2	118.0 (2)
C12—C10—C11	118.6 (2)	C14—S1—C15	90.19 (12)
N1—C1—C2—C3	177.8 (2)	C10—C12—C13—C14	176.4 (2)
C6—C1—C2—C3	−1.5 (3)	C12—C13—C14—S1	0.8 (3)
N1—C1—C2—C16	−1.6 (3)	C12—C13—C14—Cl2	−177.83 (18)
C6—C1—C2—C16	179.1 (2)	C13—C12—C15—Cl1	−177.8 (2)
C1—C2—C3—C4	−0.2 (4)	C10—C12—C15—Cl1	4.7 (4)
C16—C2—C3—C4	179.2 (2)	C13—C12—C15—S1	1.1 (3)
C2—C3—C4—C5	1.7 (4)	C10—C12—C15—S1	−176.42 (19)
C3—C4—C5—C6	−1.3 (4)	C3—C2—C16—F1	−117.2 (3)
C4—C5—C6—C1	−0.4 (4)	C1—C2—C16—F1	62.2 (3)
C4—C5—C6—C7	−179.8 (2)	C3—C2—C16—F3	121.8 (3)
N1—C1—C6—C5	−177.4 (2)	C1—C2—C16—F3	−58.8 (3)
C2—C1—C6—C5	1.8 (3)	C3—C2—C16—F2	2.7 (3)
N1—C1—C6—C7	1.9 (3)	C1—C2—C16—F2	−177.8 (2)
C2—C1—C6—C7	−178.8 (2)	C8—C9—N1—C1	−1.0 (4)
C5—C6—C7—C8	176.4 (2)	C2—C1—N1—C9	−179.3 (2)
C1—C6—C7—C8	−2.9 (3)	C6—C1—N1—C9	0.0 (3)
C5—C6—C7—N2	−3.4 (4)	C8—C7—N2—N3	1.3 (3)
C1—C6—C7—N2	177.2 (2)	C6—C7—N2—N3	−178.8 (2)
N2—C7—C8—C9	−178.1 (2)	C12—C10—N3—N2	177.7 (2)
C6—C7—C8—C9	2.1 (3)	C11—C10—N3—N2	0.5 (4)
C7—C8—C9—N1	−0.1 (4)	C7—N2—N3—C10	175.9 (2)
N3—C10—C12—C15	9.2 (4)	C13—C14—S1—C15	−0.2 (2)
C11—C10—C12—C15	−173.4 (2)	Cl2—C14—S1—C15	178.60 (17)
N3—C10—C12—C13	−168.0 (2)	C12—C15—S1—C14	−0.6 (2)
C11—C10—C12—C13	9.4 (3)	Cl1—C15—S1—C14	178.47 (16)
C15—C12—C13—C14	−1.2 (3)