3-Chloro-6-{4-[3-(trifluoro-meth-yl)phen-yl]piperazin-1-yl}pyridazine.

The title compound, C(15)H(14)ClF(3)N(4), was synthesized from 3,6-dichloro-pyridazine and 1-[3-(trifluoro-meth-yl)phen-yl]piper-azine. The piperazine ring is flanked by 3-chloro-pyridazine and 3-trifluoro-methyl-phenyl rings and adopts a chair conformation, whereas the 3-chloro-pyridazine and 3-trifluoro-methyl-phenyl rings are planar, with maximum deviations of 0.0069 (13) and 0.0133 (14) Å, respectively. The crystal structure is stabilized by weak inter-molecular C-H⋯N hydrogen-bond inter-actions.

Related literature

For the synthesis and analgesic and anti-inflammatory activity of pyridazinone and pyridazine derivatives, see: Arslan et al. (2010 ▶); Giri & Mukhopadhyay (1998 ▶); Boissier et al. (1963 ▶); Gokce et al. (2001 ▶, 2004 ▶, 2005 ▶, 2009 ▶); Sahin et al. (2004 ▶); Dundar et al. (2007 ▶). For general background to pyrazolone derivatives, see: Amir et al. (2008 ▶); Banoglu et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H14ClF3N4

M = 342.75

Monoclinic,

a = 9.461 (6) Å

b = 6.557 (4) Å

c = 24.123 (16) Å

β = 99.890 (9)°

V = 1474.1 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 173 K

0.41 × 0.25 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.888, T max = 0.932

19935 measured reflections

3385 independent reflections

2781 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.06

3385 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004137/hg2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004137/hg2643Isup2.hkl

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

C15H14ClF3N4	F(000) = 704
Mr = 342.75	Dx = 1.544 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7857 reflections
a = 9.461 (6) Å	θ = 2.2–29.7°
b = 6.557 (4) Å	µ = 0.30 mm−1
c = 24.123 (16) Å	T = 173 K
β = 99.890 (9)°	Block, colourless
V = 1474.1 (16) Å3	0.41 × 0.25 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	3385 independent reflections
Radiation source: fine-focus sealed tube	2781 reflections with I > 2σ(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.888, Tmax = 0.932	k = −8→8
19935 measured reflections	l = −31→31

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1216P] where P = (Fo2 + 2Fc2)/3
3385 reflections	(Δ/σ)max = 0.005
208 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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 > 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
C1	1.35124 (16)	0.4693 (2)	0.76675 (6)	0.0301 (3)
C2	1.23214 (15)	0.35744 (19)	0.78778 (5)	0.0228 (3)
C3	1.15571 (14)	0.45817 (19)	0.82401 (5)	0.0212 (3)
H3	1.1811	0.5939	0.8354	0.025*
C4	1.04104 (14)	0.36134 (18)	0.84400 (5)	0.0194 (3)
C5	1.01095 (15)	0.65546 (17)	0.90409 (6)	0.0235 (3)
H5A	1.0563	0.7374	0.8775	0.028*
H5B	1.0856	0.6219	0.9368	0.028*
C6	0.89367 (15)	0.78043 (18)	0.92372 (6)	0.0241 (3)
H6A	0.9364	0.9031	0.9439	0.029*
H6B	0.8240	0.8262	0.8906	0.029*
C7	0.74380 (13)	0.76537 (18)	0.99646 (5)	0.0186 (3)
C8	0.62135 (14)	0.9883 (2)	1.06758 (5)	0.0220 (3)
C9	0.60062 (14)	0.7770 (2)	1.06879 (5)	0.0236 (3)
H6	0.5458	0.7163	1.0939	0.028*
C10	0.66253 (14)	0.66193 (19)	1.03229 (5)	0.0221 (3)
H10	0.6517	0.5179	1.0309	0.027*
C11	0.76124 (14)	0.47012 (18)	0.93414 (6)	0.0223 (3)
H11A	0.6846	0.5022	0.9019	0.027*
H11B	0.7183	0.3881	0.9614	0.027*
C12	0.87797 (15)	0.34660 (18)	0.91356 (6)	0.0226 (3)
H12A	0.9476	0.2987	0.9464	0.027*
H12B	0.8344	0.2250	0.8930	0.027*
C13	1.01216 (15)	0.15733 (18)	0.82706 (5)	0.0238 (3)
H13	0.9365	0.0862	0.8399	0.029*
C14	1.09205 (16)	0.05852 (19)	0.79199 (5)	0.0277 (3)
H14	1.0708	−0.0796	0.7819	0.033*
C15	1.20215 (16)	0.1564 (2)	0.77128 (6)	0.0268 (3)
H15	1.2552	0.0886	0.7467	0.032*
Cl1	0.54631 (4)	1.14481 (6)	1.113190 (14)	0.03333 (13)
F1	1.47712 (10)	0.45600 (17)	0.80245 (4)	0.0510 (3)
F2	1.37526 (11)	0.39838 (16)	0.71726 (4)	0.0517 (3)
F3	1.32478 (10)	0.66983 (13)	0.75974 (4)	0.0438 (3)
N1	0.95396 (11)	0.46588 (15)	0.87639 (4)	0.0201 (2)
N2	0.81888 (12)	0.66056 (15)	0.96101 (4)	0.0201 (2)
N3	0.75776 (12)	0.96974 (15)	0.99729 (4)	0.0233 (3)
N4	0.69511 (12)	1.08204 (16)	1.03382 (5)	0.0248 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0290 (8)	0.0347 (7)	0.0294 (7)	−0.0006 (6)	0.0132 (6)	−0.0075 (6)
C2	0.0230 (7)	0.0259 (6)	0.0203 (6)	0.0020 (5)	0.0054 (5)	−0.0013 (5)
C3	0.0239 (7)	0.0189 (6)	0.0219 (6)	−0.0001 (5)	0.0065 (5)	−0.0028 (5)
C4	0.0236 (7)	0.0184 (6)	0.0163 (6)	0.0026 (5)	0.0040 (5)	0.0014 (4)
C5	0.0269 (7)	0.0156 (6)	0.0314 (7)	−0.0049 (5)	0.0147 (6)	−0.0026 (5)
C6	0.0318 (8)	0.0149 (5)	0.0298 (7)	−0.0027 (5)	0.0175 (6)	0.0001 (5)
C7	0.0176 (7)	0.0194 (6)	0.0189 (6)	−0.0007 (5)	0.0032 (5)	0.0011 (4)
C8	0.0196 (7)	0.0285 (6)	0.0181 (6)	0.0016 (5)	0.0038 (5)	−0.0036 (5)
C9	0.0201 (7)	0.0307 (7)	0.0211 (6)	−0.0022 (5)	0.0063 (5)	0.0041 (5)
C10	0.0225 (7)	0.0202 (6)	0.0244 (6)	−0.0025 (5)	0.0063 (5)	0.0031 (5)
C11	0.0231 (7)	0.0182 (6)	0.0274 (7)	−0.0055 (5)	0.0094 (5)	−0.0023 (5)
C12	0.0281 (8)	0.0144 (5)	0.0278 (7)	−0.0037 (5)	0.0118 (6)	−0.0007 (5)
C13	0.0314 (8)	0.0186 (6)	0.0226 (6)	−0.0027 (5)	0.0081 (6)	0.0012 (5)
C14	0.0415 (9)	0.0184 (6)	0.0237 (6)	0.0011 (6)	0.0073 (6)	−0.0026 (5)
C15	0.0324 (8)	0.0258 (7)	0.0237 (7)	0.0055 (5)	0.0089 (6)	−0.0042 (5)
Cl1	0.0347 (2)	0.0404 (2)	0.0277 (2)	0.00403 (15)	0.01307 (16)	−0.00988 (14)
F1	0.0271 (6)	0.0704 (7)	0.0556 (6)	−0.0063 (5)	0.0077 (5)	0.0012 (5)
F2	0.0615 (7)	0.0616 (6)	0.0419 (6)	−0.0158 (5)	0.0369 (5)	−0.0197 (5)
F3	0.0458 (6)	0.0321 (5)	0.0617 (6)	−0.0037 (4)	0.0324 (5)	0.0035 (4)
N1	0.0250 (6)	0.0148 (5)	0.0228 (5)	−0.0022 (4)	0.0107 (5)	−0.0010 (4)
N2	0.0239 (6)	0.0144 (5)	0.0246 (6)	−0.0032 (4)	0.0115 (5)	0.0001 (4)
N3	0.0279 (7)	0.0186 (5)	0.0261 (6)	−0.0026 (4)	0.0121 (5)	−0.0027 (4)
N4	0.0279 (7)	0.0225 (5)	0.0258 (6)	−0.0017 (5)	0.0096 (5)	−0.0057 (4)

C1—F2	1.3364 (16)	C8—N4	1.3129 (17)
C1—F3	1.3439 (18)	C8—C9	1.400 (2)
C1—F1	1.3472 (18)	C8—Cl1	1.7425 (14)
C1—C2	1.504 (2)	C9—C10	1.3654 (18)
C2—C15	1.3920 (19)	C9—H6	0.9500
C2—C3	1.3928 (18)	C10—H10	0.9500
C3—C4	1.4114 (18)	C11—N2	1.4681 (17)
C3—H3	0.9500	C11—C12	1.5199 (18)
C4—N1	1.4073 (16)	C11—H11A	0.9900
C4—C13	1.4115 (18)	C11—H11B	0.9900
C5—N1	1.4691 (17)	C12—N1	1.4676 (16)
C5—C6	1.5190 (18)	C12—H12A	0.9900
C5—H5A	0.9900	C12—H12B	0.9900
C5—H5B	0.9900	C13—C14	1.3878 (19)
C6—N2	1.4650 (16)	C13—H13	0.9500
C6—H6A	0.9900	C14—C15	1.388 (2)
C6—H6B	0.9900	C14—H14	0.9500
C7—N3	1.3462 (17)	C15—H15	0.9500
C7—N2	1.3845 (16)	N3—N4	1.3600 (15)
C7—C10	1.4236 (17)
F2—C1—F3	106.53 (12)	C10—C9—H6	121.4
F2—C1—F1	106.34 (12)	C8—C9—H6	121.4
F3—C1—F1	105.59 (12)	C9—C10—C7	117.68 (12)
F2—C1—C2	112.59 (12)	C9—C10—H10	121.2
F3—C1—C2	112.66 (11)	C7—C10—H10	121.2
F1—C1—C2	112.60 (13)	N2—C11—C12	111.21 (11)
C15—C2—C3	121.75 (12)	N2—C11—H11A	109.4
C15—C2—C1	119.53 (12)	C12—C11—H11A	109.4
C3—C2—C1	118.72 (12)	N2—C11—H11B	109.4
C2—C3—C4	120.89 (12)	C12—C11—H11B	109.4
C2—C3—H3	119.6	H11A—C11—H11B	108.0
C4—C3—H3	119.6	N1—C12—C11	112.04 (11)
N1—C4—C13	121.30 (11)	N1—C12—H12A	109.2
N1—C4—C3	121.89 (11)	C11—C12—H12A	109.2
C13—C4—C3	116.70 (11)	N1—C12—H12B	109.2
N1—C5—C6	111.56 (11)	C11—C12—H12B	109.2
N1—C5—H5A	109.3	H12A—C12—H12B	107.9
C6—C5—H5A	109.3	C14—C13—C4	121.34 (12)
N1—C5—H5B	109.3	C14—C13—H13	119.3
C6—C5—H5B	109.3	C4—C13—H13	119.3
H5A—C5—H5B	108.0	C15—C14—C13	121.65 (12)
N2—C6—C5	110.97 (11)	C15—C14—H14	119.2
N2—C6—H6A	109.4	C13—C14—H14	119.2
C5—C6—H6A	109.4	C14—C15—C2	117.62 (12)
N2—C6—H6B	109.4	C14—C15—H15	121.2
C5—C6—H6B	109.4	C2—C15—H15	121.2
H6A—C6—H6B	108.0	C4—N1—C12	118.34 (10)
N3—C7—N2	116.34 (10)	C4—N1—C5	117.42 (11)
N3—C7—C10	121.81 (11)	C12—N1—C5	110.68 (10)
N2—C7—C10	121.77 (12)	C7—N2—C6	117.79 (10)
N4—C8—C9	124.58 (11)	C7—N2—C11	120.25 (11)
N4—C8—Cl1	115.68 (10)	C6—N2—C11	111.53 (10)
C9—C8—Cl1	119.73 (10)	C7—N3—N4	119.73 (10)
C10—C9—C8	117.13 (12)	C8—N4—N3	119.05 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···N4i	0.99	2.69	3.628 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯N4i	0.99	2.69	3.628 (2)	158

Symmetry code: (i) .