3-Chloro-6-[4-(2-pyrid-yl)piperazin-1-yl]pyridazine.

In the title compound, C(13)H(14)ClN(5), the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.91 (7)°. The crystal structure is stabilized by weak inter-molecular C-H⋯N hydrogen-bond inter-actions.

Related literature

For the synthesis, structures and analgesic and anti-inflammatory activity of substituted pyridazine derivatives, see: Boissier et al. (1963 ▶); Gokce et al. (2001 ▶, 2004 ▶, 2005 ▶, 2009 ▶); Sahin et al. (2004 ▶); Dundar et al. (2007 ▶). For general background to non-opioid analgesic derivatives, see: Sato et al. (1981 ▶); Banoglu et al. (2004 ▶); Giovannoni et al. (2003 ▶)·For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H14ClN5

M = 275.74

Triclinic,

a = 5.912 (3) Å

b = 8.088 (5) Å

c = 13.689 (8) Å

α = 83.359 (9)°

β = 83.019 (9)°

γ = 75.168 (9)°

V = 625.5 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.16 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.954, T max = 0.959

11395 measured reflections

3275 independent reflections

2264 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.095

S = 0.95

3275 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker (2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809050727/hg2610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050727/hg2610Isup2.hkl

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

C13H14ClN5	Z = 2
Mr = 275.74	F(000) = 288
Triclinic, P1	Dx = 1.464 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.912 (3) Å	Cell parameters from 2718 reflections
b = 8.088 (5) Å	θ = 2.6–28.2°
c = 13.689 (8) Å	µ = 0.30 mm−1
α = 83.359 (9)°	T = 296 K
β = 83.019 (9)°	Block, colourless
γ = 75.168 (9)°	0.16 × 0.15 × 0.14 mm
V = 625.5 (6) Å3

Bruker APEXII CCD diffractometer	3275 independent reflections
Radiation source: fine-focus sealed tube	2264 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 29.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→7
Tmin = 0.954, Tmax = 0.959	k = −10→11
11395 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0433P)2] where P = (Fo2 + 2Fc2)/3
3275 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.23 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 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
C1	0.2600 (3)	1.08679 (18)	0.14549 (10)	0.0258 (3)
C2	0.4977 (3)	1.05027 (18)	0.15814 (10)	0.0262 (3)
H2	0.6045	1.0856	0.1098	0.031*
C3	0.5676 (2)	0.96086 (18)	0.24396 (10)	0.0233 (3)
H3	0.7248	0.9314	0.2563	0.028*
C4	0.3929 (2)	0.91394 (16)	0.31412 (10)	0.0183 (3)
C5	0.2554 (2)	0.78257 (18)	0.47211 (9)	0.0191 (3)
H5A	0.2447	0.6710	0.4565	0.023*
H5B	0.1066	0.8639	0.4613	0.023*
C6	0.2997 (2)	0.77262 (18)	0.57925 (10)	0.0201 (3)
H6A	0.2902	0.8869	0.5973	0.024*
H6B	0.1795	0.7281	0.6206	0.024*
C7	0.7198 (2)	0.71363 (18)	0.53092 (9)	0.0195 (3)
H7A	0.8676	0.6312	0.5417	0.023*
H7B	0.7325	0.8246	0.5467	0.023*
C8	0.6760 (2)	0.72468 (17)	0.42325 (10)	0.0191 (3)
H8A	0.7957	0.7701	0.3822	0.023*
H8B	0.6860	0.6107	0.4047	0.023*
C9	0.5772 (2)	0.58513 (17)	0.69070 (10)	0.0195 (3)
C10	0.3966 (3)	0.57581 (19)	0.76644 (11)	0.0273 (3)
H10	0.2411	0.6307	0.7571	0.033*
C11	0.4545 (3)	0.4840 (2)	0.85437 (11)	0.0326 (4)
H11	0.3373	0.4754	0.9052	0.039*
C12	0.6857 (3)	0.4044 (2)	0.86779 (11)	0.0335 (4)
H12	0.7277	0.3393	0.9263	0.040*
C13	0.8513 (3)	0.4253 (2)	0.79115 (11)	0.0317 (4)
H13	1.0080	0.3743	0.8002	0.038*
Cl1	0.15611 (8)	1.19962 (6)	0.03723 (3)	0.04376 (16)
N1	0.1002 (2)	1.04206 (16)	0.21036 (9)	0.0273 (3)
N2	0.1664 (2)	0.95301 (15)	0.29644 (8)	0.0240 (3)
N3	0.44321 (19)	0.83591 (14)	0.40660 (8)	0.0185 (3)
N4	0.53064 (19)	0.66186 (14)	0.59658 (8)	0.0190 (3)
N5	0.8031 (2)	0.51407 (15)	0.70410 (9)	0.0259 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0272 (8)	0.0267 (8)	0.0218 (7)	−0.0052 (6)	−0.0029 (6)	0.0016 (6)
C2	0.0253 (8)	0.0305 (8)	0.0236 (7)	−0.0119 (7)	0.0053 (6)	−0.0019 (6)
C3	0.0171 (7)	0.0278 (8)	0.0256 (7)	−0.0084 (6)	0.0024 (6)	−0.0035 (6)
C4	0.0171 (7)	0.0169 (7)	0.0215 (7)	−0.0052 (5)	0.0011 (5)	−0.0050 (5)
C5	0.0120 (7)	0.0230 (7)	0.0219 (7)	−0.0054 (6)	0.0007 (5)	−0.0006 (5)
C6	0.0129 (7)	0.0240 (7)	0.0220 (7)	−0.0033 (6)	0.0015 (5)	−0.0015 (6)
C7	0.0121 (7)	0.0226 (7)	0.0239 (7)	−0.0057 (6)	−0.0001 (5)	−0.0010 (5)
C8	0.0107 (7)	0.0217 (7)	0.0239 (7)	−0.0031 (5)	0.0017 (5)	−0.0028 (5)
C9	0.0198 (7)	0.0182 (7)	0.0219 (7)	−0.0057 (6)	−0.0031 (6)	−0.0033 (5)
C10	0.0208 (8)	0.0327 (8)	0.0262 (8)	−0.0048 (7)	−0.0005 (6)	0.0011 (6)
C11	0.0320 (9)	0.0415 (9)	0.0236 (8)	−0.0123 (8)	0.0016 (7)	0.0023 (7)
C12	0.0369 (10)	0.0389 (9)	0.0240 (8)	−0.0077 (8)	−0.0103 (7)	0.0045 (7)
C13	0.0246 (9)	0.0378 (9)	0.0314 (8)	−0.0030 (7)	−0.0101 (7)	0.0000 (7)
Cl1	0.0423 (3)	0.0562 (3)	0.0281 (2)	−0.0095 (2)	−0.00750 (18)	0.01386 (18)
N1	0.0230 (7)	0.0329 (7)	0.0246 (6)	−0.0060 (6)	−0.0038 (5)	0.0034 (5)
N2	0.0166 (6)	0.0297 (7)	0.0242 (6)	−0.0054 (5)	−0.0023 (5)	0.0033 (5)
N3	0.0115 (6)	0.0229 (6)	0.0198 (6)	−0.0039 (5)	0.0009 (4)	0.0001 (5)
N4	0.0119 (6)	0.0230 (6)	0.0209 (6)	−0.0042 (5)	0.0003 (5)	0.0007 (5)
N5	0.0201 (7)	0.0307 (7)	0.0259 (7)	−0.0037 (5)	−0.0052 (5)	−0.0014 (5)

C1—N1	1.3071 (19)	C7—H7A	0.9700
C1—C2	1.388 (2)	C7—H7B	0.9700
C1—Cl1	1.7401 (16)	C8—N3	1.4661 (18)
C2—C3	1.3574 (19)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.4170 (18)	C9—N5	1.3377 (18)
C3—H3	0.9300	C9—N4	1.3909 (17)
C4—N2	1.3401 (18)	C9—C10	1.405 (2)
C4—N3	1.3784 (17)	C10—C11	1.372 (2)
C5—N3	1.4617 (17)	C10—H10	0.9300
C5—C6	1.5104 (19)	C11—C12	1.378 (2)
C5—H5A	0.9700	C11—H11	0.9300
C5—H5B	0.9700	C12—C13	1.372 (2)
C6—N4	1.4582 (18)	C12—H12	0.9300
C6—H6A	0.9700	C13—N5	1.3402 (18)
C6—H6B	0.9700	C13—H13	0.9300
C7—N4	1.4635 (17)	N1—N2	1.3534 (16)
C7—C8	1.5159 (19)
N1—C1—C2	124.64 (13)	N3—C8—C7	110.54 (11)
N1—C1—Cl1	115.24 (12)	N3—C8—H8A	109.5
C2—C1—Cl1	120.12 (11)	C7—C8—H8A	109.5
C3—C2—C1	117.20 (13)	N3—C8—H8B	109.5
C3—C2—H2	121.4	C7—C8—H8B	109.5
C1—C2—H2	121.4	H8A—C8—H8B	108.1
C2—C3—C4	117.76 (14)	N5—C9—N4	116.30 (12)
C2—C3—H3	121.1	N5—C9—C10	121.67 (13)
C4—C3—H3	121.1	N4—C9—C10	121.97 (13)
N2—C4—N3	116.16 (11)	C11—C10—C9	118.58 (14)
N2—C4—C3	121.66 (12)	C11—C10—H10	120.7
N3—C4—C3	122.04 (13)	C9—C10—H10	120.7
N3—C5—C6	111.31 (11)	C10—C11—C12	120.29 (14)
N3—C5—H5A	109.4	C10—C11—H11	119.9
C6—C5—H5A	109.4	C12—C11—H11	119.9
N3—C5—H5B	109.4	C13—C12—C11	117.17 (14)
C6—C5—H5B	109.4	C13—C12—H12	121.4
H5A—C5—H5B	108.0	C11—C12—H12	121.4
N4—C6—C5	110.91 (11)	N5—C13—C12	124.63 (14)
N4—C6—H6A	109.5	N5—C13—H13	117.7
C5—C6—H6A	109.5	C12—C13—H13	117.7
N4—C6—H6B	109.5	C1—N1—N2	119.04 (12)
C5—C6—H6B	109.5	C4—N2—N1	119.68 (11)
H6A—C6—H6B	108.0	C4—N3—C5	118.35 (11)
N4—C7—C8	111.62 (11)	C4—N3—C8	121.18 (11)
N4—C7—H7A	109.3	C5—N3—C8	112.41 (11)
C8—C7—H7A	109.3	C9—N4—C6	120.47 (11)
N4—C7—H7B	109.3	C9—N4—C7	118.98 (11)
C8—C7—H7B	109.3	C6—N4—C7	112.49 (11)
H7A—C7—H7B	108.0	C9—N5—C13	117.56 (12)
N1—C1—C2—C3	0.4 (2)	C3—C4—N3—C5	−176.37 (12)
Cl1—C1—C2—C3	−179.57 (11)	N2—C4—N3—C8	154.15 (12)
C1—C2—C3—C4	−0.8 (2)	C3—C4—N3—C8	−30.0 (2)
C2—C3—C4—N2	1.2 (2)	C6—C5—N3—C4	−155.41 (12)
C2—C3—C4—N3	−174.44 (13)	C6—C5—N3—C8	55.41 (15)
N3—C5—C6—N4	−54.49 (15)	C7—C8—N3—C4	157.23 (12)
N4—C7—C8—N3	53.56 (15)	C7—C8—N3—C5	−54.57 (15)
N5—C9—C10—C11	−3.3 (2)	N5—C9—N4—C6	−167.32 (12)
N4—C9—C10—C11	173.85 (13)	C10—C9—N4—C6	15.4 (2)
C9—C10—C11—C12	0.6 (2)	N5—C9—N4—C7	−20.90 (18)
C10—C11—C12—C13	1.6 (3)	C10—C9—N4—C7	161.84 (13)
C11—C12—C13—N5	−1.5 (3)	C5—C6—N4—C9	−156.99 (12)
C2—C1—N1—N2	−0.3 (2)	C5—C6—N4—C7	54.58 (15)
Cl1—C1—N1—N2	179.64 (10)	C8—C7—N4—C9	156.51 (12)
N3—C4—N2—N1	174.73 (12)	C8—C7—N4—C6	−54.56 (15)
C3—C4—N2—N1	−1.2 (2)	N4—C9—N5—C13	−173.88 (13)
C1—N1—N2—C4	0.7 (2)	C10—C9—N5—C13	3.4 (2)
N2—C4—N3—C5	7.76 (18)	C12—C13—N5—C9	−1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.93	2.58	3.346 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.93	2.58	3.346 (3)	140

Symmetry code: (i) .