(2E)-1-[2,3-Dichloro-6-methyl-5-(trifluoro-meth-yl)phen-yl]-2-(1-phenyl-ethyl-idene)hydrazine.

The title compound, C(16)H(13)Cl(2)F(3)N(2), exists in an E conformation with respect to the C=N bond [1.2952 (11) Å] and the C-N-N=C torsion angle is 175.65 (8)°. The dihedral angle between the benzene rings is 42.09 (4)°. An intra-molecular C-H⋯F hydrogen bond generates an S(6) ring. In the crystal, the mol-ecules are linked into [101] chains by C-H⋯F hydrogen bonds.

Related literature

For background to the properties and applications of hydrazones, see: Barbazan et al. (2008 ▶); Banerjee et al. (2009 ▶); Ghavtadze et al. (2008 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H13Cl2F3N2

M = 361.18

Monoclinic,

a = 11.2600 (16) Å

b = 11.4025 (17) Å

c = 14.8398 (16) Å

β = 123.773 (7)°

V = 1583.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 100 K

0.32 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII Duo CCD diffractometer

Absorption correction: multi-scan (SADABS); Bruker, 2009 ▶) T min = 0.872, T max = 0.911

22269 measured reflections

5714 independent reflections

5043 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.090

S = 1.02

5714 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042419/hb6964sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042419/hb6964Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042419/hb6964Isup3.cml

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

C16H13Cl2F3N2	F(000) = 736
Mr = 361.18	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9943 reflections
a = 11.2600 (16) Å	θ = 2.4–32.6°
b = 11.4025 (17) Å	µ = 0.44 mm−1
c = 14.8398 (16) Å	T = 100 K
β = 123.773 (7)°	Block, yellow
V = 1583.8 (4) Å3	0.32 × 0.26 × 0.22 mm
Z = 4

Bruker SMART APEXII Duo CCD diffractometer	5714 independent reflections
Radiation source: fine-focus sealed tube	5043 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 32.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS); Bruker, 2009)	h = −17→17
Tmin = 0.872, Tmax = 0.911	k = −17→16
22269 measured reflections	l = −22→22

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.4114P] where P = (Fo2 + 2Fc2)/3
5714 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.07133 (2)	0.57463 (2)	0.919947 (18)	0.02243 (6)
Cl2	0.27412 (3)	0.51560 (3)	1.16881 (2)	0.03137 (7)
F1	0.76376 (7)	0.64100 (7)	1.26985 (6)	0.04073 (19)
F2	0.72355 (7)	0.79611 (5)	1.17471 (5)	0.02773 (13)
F3	0.76971 (7)	0.63239 (6)	1.12760 (7)	0.03906 (18)
N1	0.24945 (8)	0.64196 (7)	0.75151 (6)	0.01758 (13)
N2	0.21577 (8)	0.68019 (7)	0.82355 (6)	0.01970 (14)
H1	0.1231	0.6830	0.7982	0.024*
C1	0.08557 (10)	0.60301 (8)	0.46427 (7)	0.02097 (16)
H1A	−0.0116	0.6165	0.4387	0.025*
C2	0.11987 (11)	0.56352 (9)	0.39242 (8)	0.02343 (17)
H2A	0.0464	0.5506	0.3184	0.028*
C3	0.26177 (11)	0.54303 (8)	0.42924 (8)	0.02305 (17)
H3A	0.2855	0.5160	0.3806	0.028*
C4	0.36909 (10)	0.56246 (8)	0.53808 (8)	0.02125 (16)
H4A	0.4660	0.5484	0.5634	0.026*
C5	0.33508 (9)	0.60236 (7)	0.60973 (7)	0.01782 (15)
H5A	0.4090	0.6157	0.6836	0.021*
C6	0.19245 (9)	0.62302 (7)	0.57366 (7)	0.01647 (14)
C7	0.15569 (9)	0.66423 (7)	0.65008 (7)	0.01714 (14)
C8	0.30910 (9)	0.65100 (7)	0.93301 (7)	0.01651 (14)
C9	0.45661 (9)	0.67664 (7)	0.98943 (7)	0.01764 (15)
C10	0.54176 (9)	0.65007 (7)	1.10045 (7)	0.01872 (15)
C11	0.48613 (10)	0.60149 (8)	1.15569 (7)	0.02078 (16)
H11A	0.5468	0.5845	1.2309	0.025*
C12	0.34106 (10)	0.57840 (8)	1.09936 (7)	0.01957 (15)
C13	0.25253 (9)	0.60334 (8)	0.98898 (7)	0.01731 (14)
C14	0.01767 (10)	0.72840 (9)	0.60945 (8)	0.02298 (17)
H14A	0.0361	0.7958	0.6565	0.034*
H14B	−0.0503	0.6753	0.6102	0.034*
H14C	−0.0225	0.7558	0.5353	0.034*
C15	0.51547 (11)	0.73642 (9)	0.93086 (8)	0.02373 (17)
H15A	0.6001	0.7824	0.9828	0.036*
H15B	0.4426	0.7885	0.8747	0.036*
H15C	0.5418	0.6770	0.8972	0.036*
C16	0.69874 (10)	0.67904 (8)	1.16736 (8)	0.02398 (18)

	U11	U22	U33	U12	U13	U23
Cl1	0.01517 (9)	0.02920 (11)	0.02257 (11)	−0.00304 (7)	0.01028 (8)	−0.00384 (7)
Cl2	0.02648 (12)	0.04378 (15)	0.02537 (12)	−0.00394 (10)	0.01537 (10)	0.00792 (10)
F1	0.0198 (3)	0.0430 (4)	0.0341 (4)	−0.0034 (3)	−0.0007 (3)	0.0151 (3)
F2	0.0243 (3)	0.0190 (3)	0.0311 (3)	−0.0060 (2)	0.0099 (2)	−0.0040 (2)
F3	0.0199 (3)	0.0342 (3)	0.0623 (5)	−0.0027 (2)	0.0223 (3)	−0.0143 (3)
N1	0.0180 (3)	0.0189 (3)	0.0170 (3)	0.0008 (2)	0.0105 (3)	−0.0012 (2)
N2	0.0173 (3)	0.0259 (4)	0.0161 (3)	0.0032 (3)	0.0094 (3)	−0.0008 (3)
C1	0.0184 (4)	0.0250 (4)	0.0172 (4)	−0.0010 (3)	0.0084 (3)	−0.0001 (3)
C2	0.0270 (4)	0.0244 (4)	0.0171 (4)	−0.0028 (3)	0.0111 (3)	−0.0015 (3)
C3	0.0314 (5)	0.0200 (4)	0.0232 (4)	0.0004 (3)	0.0185 (4)	−0.0007 (3)
C4	0.0228 (4)	0.0206 (4)	0.0244 (4)	0.0031 (3)	0.0157 (4)	0.0015 (3)
C5	0.0176 (3)	0.0176 (3)	0.0181 (3)	0.0016 (3)	0.0099 (3)	0.0014 (3)
C6	0.0168 (3)	0.0161 (3)	0.0162 (3)	0.0004 (3)	0.0090 (3)	0.0011 (3)
C7	0.0163 (3)	0.0177 (3)	0.0179 (3)	0.0009 (3)	0.0098 (3)	0.0005 (3)
C8	0.0161 (3)	0.0164 (3)	0.0171 (3)	0.0004 (3)	0.0092 (3)	−0.0019 (3)
C9	0.0168 (3)	0.0158 (3)	0.0209 (4)	−0.0007 (3)	0.0109 (3)	−0.0021 (3)
C10	0.0144 (3)	0.0156 (3)	0.0222 (4)	0.0002 (3)	0.0077 (3)	−0.0005 (3)
C11	0.0181 (4)	0.0196 (4)	0.0195 (4)	0.0005 (3)	0.0072 (3)	0.0025 (3)
C12	0.0185 (4)	0.0203 (4)	0.0199 (4)	−0.0006 (3)	0.0106 (3)	0.0016 (3)
C13	0.0144 (3)	0.0185 (3)	0.0183 (4)	−0.0005 (3)	0.0086 (3)	−0.0019 (3)
C14	0.0196 (4)	0.0267 (4)	0.0234 (4)	0.0066 (3)	0.0125 (3)	0.0042 (3)
C15	0.0228 (4)	0.0257 (4)	0.0258 (4)	−0.0059 (3)	0.0155 (4)	−0.0041 (3)
C16	0.0165 (4)	0.0191 (4)	0.0288 (4)	−0.0009 (3)	0.0079 (3)	0.0006 (3)

Cl1—C13	1.7309 (9)	C5—H5A	0.9500
Cl2—C12	1.7340 (10)	C6—C7	1.4833 (12)
F1—C16	1.3414 (12)	C7—C14	1.5075 (12)
F2—C16	1.3558 (11)	C8—C13	1.4069 (12)
F3—C16	1.3394 (13)	C8—C9	1.4139 (12)
N1—C7	1.2952 (11)	C9—C10	1.4032 (13)
N1—N2	1.3884 (10)	C9—C15	1.5165 (13)
N2—C8	1.3985 (11)	C10—C11	1.3936 (13)
N2—H1	0.8915	C10—C16	1.5060 (13)
C1—C2	1.3951 (13)	C11—C12	1.3850 (13)
C1—C6	1.4013 (12)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.3936 (12)
C2—C3	1.3912 (15)	C14—H14A	0.9800
C2—H2A	0.9500	C14—H14B	0.9800
C3—C4	1.3958 (14)	C14—H14C	0.9800
C3—H3A	0.9500	C15—H15A	0.9800
C4—C5	1.3916 (12)	C15—H15B	0.9800
C4—H4A	0.9500	C15—H15C	0.9800
C5—C6	1.4020 (12)
C7—N1—N2	115.99 (7)	C11—C10—C9	122.64 (8)
N1—N2—C8	117.97 (7)	C11—C10—C16	116.48 (8)
N1—N2—H1	116.3	C9—C10—C16	120.81 (8)
C8—N2—H1	116.5	C12—C11—C10	119.05 (8)
C2—C1—C6	120.91 (8)	C12—C11—H11A	120.5
C2—C1—H1A	119.5	C10—C11—H11A	120.5
C6—C1—H1A	119.5	C11—C12—C13	120.24 (8)
C3—C2—C1	119.96 (9)	C11—C12—Cl2	118.45 (7)
C3—C2—H2A	120.0	C13—C12—Cl2	121.31 (7)
C1—C2—H2A	120.0	C12—C13—C8	120.66 (8)
C2—C3—C4	119.63 (9)	C12—C13—Cl1	119.65 (7)
C2—C3—H3A	120.2	C8—C13—Cl1	119.69 (7)
C4—C3—H3A	120.2	C7—C14—H14A	109.5
C5—C4—C3	120.47 (9)	C7—C14—H14B	109.5
C5—C4—H4A	119.8	H14A—C14—H14B	109.5
C3—C4—H4A	119.8	C7—C14—H14C	109.5
C4—C5—C6	120.44 (8)	H14A—C14—H14C	109.5
C4—C5—H5A	119.8	H14B—C14—H14C	109.5
C6—C5—H5A	119.8	C9—C15—H15A	109.5
C1—C6—C5	118.60 (8)	C9—C15—H15B	109.5
C1—C6—C7	120.82 (8)	H15A—C15—H15B	109.5
C5—C6—C7	120.57 (7)	C9—C15—H15C	109.5
N1—C7—C6	115.64 (7)	H15A—C15—H15C	109.5
N1—C7—C14	123.57 (8)	H15B—C15—H15C	109.5
C6—C7—C14	120.78 (7)	F3—C16—F1	106.72 (9)
N2—C8—C13	118.89 (8)	F3—C16—F2	106.25 (8)
N2—C8—C9	121.03 (8)	F1—C16—F2	105.61 (8)
C13—C8—C9	119.91 (8)	F3—C16—C10	113.04 (8)
C10—C9—C8	117.49 (8)	F1—C16—C10	112.18 (8)
C10—C9—C15	122.61 (8)	F2—C16—C10	112.51 (8)
C8—C9—C15	119.82 (8)
C7—N1—N2—C8	175.65 (8)	C15—C9—C10—C11	176.09 (8)
C6—C1—C2—C3	0.26 (14)	C8—C9—C10—C16	−177.55 (8)
C1—C2—C3—C4	−0.15 (14)	C15—C9—C10—C16	−0.72 (13)
C2—C3—C4—C5	−0.14 (14)	C9—C10—C11—C12	−0.09 (14)
C3—C4—C5—C6	0.32 (13)	C16—C10—C11—C12	176.85 (8)
C2—C1—C6—C5	−0.09 (13)	C10—C11—C12—C13	0.13 (14)
C2—C1—C6—C7	−179.58 (8)	C10—C11—C12—Cl2	178.90 (7)
C4—C5—C6—C1	−0.21 (13)	C11—C12—C13—C8	0.68 (13)
C4—C5—C6—C7	179.29 (8)	Cl2—C12—C13—C8	−178.05 (7)
N2—N1—C7—C6	−179.96 (7)	C11—C12—C13—Cl1	−179.68 (7)
N2—N1—C7—C14	0.51 (13)	Cl2—C12—C13—Cl1	1.59 (11)
C1—C6—C7—N1	157.04 (8)	N2—C8—C13—C12	−176.86 (8)
C5—C6—C7—N1	−22.44 (12)	C9—C8—C13—C12	−1.53 (13)
C1—C6—C7—C14	−23.41 (12)	N2—C8—C13—Cl1	3.50 (11)
C5—C6—C7—C14	157.11 (8)	C9—C8—C13—Cl1	178.83 (6)
N1—N2—C8—C13	−131.65 (8)	C11—C10—C16—F3	127.38 (9)
N1—N2—C8—C9	53.07 (11)	C9—C10—C16—F3	−55.61 (12)
N2—C8—C9—C10	176.75 (8)	C11—C10—C16—F1	6.65 (12)
C13—C8—C9—C10	1.52 (12)	C9—C10—C16—F1	−176.35 (8)
N2—C8—C9—C15	−0.17 (12)	C11—C10—C16—F2	−112.26 (10)
C13—C8—C9—C15	−175.40 (8)	C9—C10—C16—F2	64.74 (12)
C8—C9—C10—C11	−0.74 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F1i	0.95	2.39	3.1652 (14)	139
C15—H15A···F2	0.98	2.38	3.1018 (13)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯F1i	0.95	2.39	3.1652 (14)	139
C15—H15A⋯F2	0.98	2.38	3.1018 (13)	130

Symmetry code: (i) .