3-Chloro-6-{4-[3-(4-chloro-phen-oxy)prop-yl]piperazin-1-yl}pyridazine.

In the title compound, C(17)H(20)Cl(2)N(4)O, the piperazine ring adopts a chair conformation and the dihedral angle between the pyridazine ring and the benzene ring is 36.3 (1)°. In the crystal, weak C-H⋯O and C-H⋯(N,N) inter-actions help to establish the packing, which also features short inter-molecular Cl⋯Cl contacts [3.331 (2) Å].

Related literature

For the biological properties of 3-(piperazin-1-yl)pyridazine derivatives, see: Monge et al. (1991 ▶); Tucker et al. (1998 ▶). For the synthesis, see: Fan et al. (2009 ▶).

Experimental

Crystal data

C17H20Cl2N4O

M = 367.27

Monoclinic,

a = 39.774 (18) Å

b = 5.757 (3) Å

c = 14.924 (7) Å

β = 93.107 (9)°

V = 3412 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.39 mm−1

T = 113 K

0.20 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.926, T max = 0.969

11904 measured reflections

2996 independent reflections

2030 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.159

S = 1.09

2996 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005337/hb5330sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005337/hb5330Isup2.hkl

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

C17H20Cl2N4O	F(000) = 1536
Mr = 367.27	Dx = 1.430 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.774 (18) Å	Cell parameters from 5597 reflections
b = 5.757 (3) Å	θ = 2.1–28.0°
c = 14.924 (7) Å	µ = 0.39 mm−1
β = 93.107 (9)°	T = 113 K
V = 3412 (3) Å3	Prism, colourless
Z = 8	0.20 × 0.18 × 0.08 mm

Rigaku Saturn CCD area-detector diffractometer	2996 independent reflections
Radiation source: rotating anode	2030 reflections with I > 2σ(I)
multilayer	Rint = 0.061
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 2.1°
ω and φ scans	h = −46→46
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −6→6
Tmin = 0.926, Tmax = 0.969	l = −15→17
11904 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0834P)2] where P = (Fo2 + 2Fc2)/3
2996 reflections	(Δ/σ)max = 0.003
217 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.33 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
Cl1	1.06826 (2)	−0.31802 (19)	0.30198 (6)	0.0238 (3)
Cl2	0.64299 (2)	0.03379 (19)	0.75503 (6)	0.0252 (3)
O1	0.77076 (5)	0.0299 (4)	0.57543 (16)	0.0172 (6)
N1	1.01144 (7)	−0.4149 (6)	0.37004 (19)	0.0191 (8)
N2	0.98066 (6)	−0.3697 (6)	0.40118 (19)	0.0177 (7)
N3	0.93922 (6)	−0.1129 (5)	0.44101 (19)	0.0159 (7)
N4	0.87083 (6)	−0.0635 (5)	0.49145 (19)	0.0149 (7)
C1	1.02999 (8)	−0.2401 (7)	0.3457 (2)	0.0177 (9)
C2	1.02128 (8)	−0.0067 (7)	0.3520 (2)	0.0182 (9)
H2	1.0360	0.1133	0.3349	0.022*
C3	0.99070 (8)	0.0412 (7)	0.3837 (2)	0.0182 (8)
H3	0.9832	0.1967	0.3898	0.022*
C4	0.97035 (8)	−0.1495 (7)	0.4072 (2)	0.0154 (8)
C5	0.92000 (8)	−0.3152 (7)	0.4675 (2)	0.0180 (8)
H5A	0.9353	−0.4301	0.4975	0.022*
H5B	0.9090	−0.3892	0.4137	0.022*
C6	0.89344 (8)	−0.2413 (7)	0.5311 (2)	0.0179 (9)
H6A	0.8800	−0.3786	0.5471	0.021*
H6B	0.9047	−0.1797	0.5869	0.021*
C7	0.89091 (8)	0.1374 (7)	0.4665 (2)	0.0156 (8)
H7A	0.9021	0.2057	0.5212	0.019*
H7B	0.8759	0.2569	0.4384	0.019*
C8	0.91722 (8)	0.0697 (7)	0.4018 (2)	0.0164 (8)
H8A	0.9060	0.0130	0.3451	0.020*
H8B	0.9309	0.2074	0.3879	0.020*
C9	0.84595 (8)	−0.0032 (7)	0.5562 (2)	0.0169 (8)
H9A	0.8579	0.0471	0.6128	0.020*
H9B	0.8328	−0.1438	0.5694	0.020*
C10	0.82186 (8)	0.1877 (7)	0.5241 (2)	0.0169 (8)
H10A	0.8346	0.3345	0.5193	0.020*
H10B	0.8123	0.1478	0.4635	0.020*
C11	0.79342 (8)	0.2255 (7)	0.5855 (2)	0.0158 (8)
H11A	0.8024	0.2378	0.6485	0.019*
H11B	0.7814	0.3713	0.5693	0.019*
C12	0.74176 (8)	0.0403 (7)	0.6207 (2)	0.0146 (8)
C13	0.71859 (8)	−0.1366 (7)	0.6022 (2)	0.0171 (8)
H13	0.7236	−0.2563	0.5612	0.020*
C14	0.68822 (8)	−0.1390 (7)	0.6433 (2)	0.0163 (8)
H14	0.6723	−0.2587	0.6301	0.020*
C15	0.68135 (8)	0.0346 (7)	0.7035 (2)	0.0169 (8)
C16	0.70436 (8)	0.2093 (7)	0.7240 (2)	0.0181 (8)
H16	0.6995	0.3259	0.7664	0.022*
C17	0.73474 (8)	0.2130 (7)	0.6819 (2)	0.0167 (8)
H17	0.7506	0.3331	0.6951	0.020*

	U11	U22	U33	U12	U13	U23
Cl1	0.0167 (5)	0.0310 (7)	0.0242 (5)	0.0050 (4)	0.0056 (4)	0.0013 (4)
Cl2	0.0177 (5)	0.0342 (7)	0.0246 (5)	−0.0029 (4)	0.0080 (4)	−0.0021 (4)
O1	0.0139 (12)	0.0165 (16)	0.0217 (14)	−0.0030 (11)	0.0047 (10)	−0.0055 (12)
N1	0.0185 (15)	0.018 (2)	0.0211 (17)	0.0044 (13)	0.0046 (13)	0.0023 (14)
N2	0.0160 (15)	0.015 (2)	0.0222 (17)	0.0029 (13)	0.0045 (12)	0.0017 (14)
N3	0.0141 (14)	0.0119 (19)	0.0220 (17)	0.0007 (12)	0.0046 (12)	0.0033 (13)
N4	0.0135 (14)	0.0108 (19)	0.0207 (16)	0.0004 (12)	0.0046 (12)	0.0012 (13)
C1	0.0127 (16)	0.024 (3)	0.0170 (18)	0.0020 (16)	0.0017 (14)	−0.0004 (17)
C2	0.0168 (18)	0.017 (3)	0.021 (2)	−0.0021 (16)	0.0000 (15)	0.0007 (17)
C3	0.0179 (18)	0.014 (2)	0.022 (2)	0.0014 (15)	0.0007 (15)	0.0009 (17)
C4	0.0165 (17)	0.013 (2)	0.0164 (19)	0.0002 (15)	−0.0012 (14)	−0.0008 (16)
C5	0.0167 (17)	0.012 (2)	0.026 (2)	0.0007 (16)	0.0029 (15)	0.0022 (17)
C6	0.0166 (17)	0.013 (2)	0.024 (2)	−0.0004 (15)	0.0030 (14)	0.0042 (16)
C7	0.0166 (17)	0.011 (2)	0.020 (2)	0.0008 (15)	0.0024 (14)	0.0008 (16)
C8	0.0179 (17)	0.015 (2)	0.0172 (19)	0.0014 (15)	0.0034 (14)	0.0037 (16)
C9	0.0165 (17)	0.017 (2)	0.0170 (19)	−0.0013 (16)	0.0017 (14)	0.0026 (16)
C10	0.0167 (17)	0.015 (2)	0.0197 (19)	−0.0008 (15)	0.0038 (14)	0.0008 (16)
C11	0.0158 (17)	0.012 (2)	0.0197 (19)	−0.0019 (15)	0.0014 (14)	0.0010 (16)
C12	0.0130 (17)	0.016 (2)	0.0153 (18)	0.0018 (15)	0.0008 (13)	0.0033 (16)
C13	0.0194 (18)	0.014 (2)	0.0174 (19)	0.0016 (16)	0.0000 (14)	−0.0024 (16)
C14	0.0176 (17)	0.015 (2)	0.0166 (19)	−0.0045 (15)	−0.0015 (14)	0.0020 (16)
C15	0.0134 (17)	0.021 (2)	0.0166 (19)	0.0017 (16)	0.0036 (14)	0.0041 (16)
C16	0.0205 (18)	0.017 (2)	0.0164 (19)	0.0034 (16)	0.0002 (14)	−0.0034 (16)
C17	0.0157 (17)	0.018 (2)	0.0164 (19)	−0.0034 (15)	−0.0006 (14)	0.0004 (16)

Cl1—C1	1.747 (3)	C7—C8	1.513 (4)
Cl2—C15	1.745 (3)	C7—H7A	0.9900
O1—C12	1.369 (4)	C7—H7B	0.9900
O1—C11	1.445 (4)	C8—H8A	0.9900
N1—C1	1.311 (5)	C8—H8B	0.9900
N1—N2	1.358 (4)	C9—C10	1.518 (5)
N2—C4	1.337 (5)	C9—H9A	0.9900
N3—C4	1.378 (4)	C9—H9B	0.9900
N3—C5	1.459 (5)	C10—C11	1.509 (5)
N3—C8	1.469 (4)	C10—H10A	0.9900
N4—C9	1.462 (4)	C10—H10B	0.9900
N4—C7	1.465 (4)	C11—H11A	0.9900
N4—C6	1.466 (4)	C11—H11B	0.9900
C1—C2	1.392 (5)	C12—C17	1.389 (5)
C2—C3	1.357 (5)	C12—C13	1.391 (5)
C2—H2	0.9500	C13—C14	1.383 (5)
C3—C4	1.419 (5)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.382 (5)
C5—C6	1.518 (5)	C14—H14	0.9500
C5—H5A	0.9900	C15—C16	1.383 (5)
C5—H5B	0.9900	C16—C17	1.392 (5)
C6—H6A	0.9900	C16—H16	0.9500
C6—H6B	0.9900	C17—H17	0.9500
C12—O1—C11	116.9 (3)	C7—C8—H8A	109.6
C1—N1—N2	118.6 (3)	N3—C8—H8B	109.6
C4—N2—N1	119.4 (3)	C7—C8—H8B	109.6
C4—N3—C5	118.2 (3)	H8A—C8—H8B	108.1
C4—N3—C8	119.4 (3)	N4—C9—C10	113.7 (3)
C5—N3—C8	111.7 (3)	N4—C9—H9A	108.8
C9—N4—C7	112.2 (3)	C10—C9—H9A	108.8
C9—N4—C6	108.8 (3)	N4—C9—H9B	108.8
C7—N4—C6	108.8 (3)	C10—C9—H9B	108.8
N1—C1—C2	125.2 (3)	H9A—C9—H9B	107.7
N1—C1—Cl1	114.9 (3)	C11—C10—C9	113.2 (3)
C2—C1—Cl1	119.9 (3)	C11—C10—H10A	108.9
C3—C2—C1	116.8 (3)	C9—C10—H10A	108.9
C3—C2—H2	121.6	C11—C10—H10B	108.9
C1—C2—H2	121.6	C9—C10—H10B	108.9
C2—C3—C4	117.6 (4)	H10A—C10—H10B	107.7
C2—C3—H3	121.2	O1—C11—C10	108.0 (3)
C4—C3—H3	121.2	O1—C11—H11A	110.1
N2—C4—N3	117.0 (3)	C10—C11—H11A	110.1
N2—C4—C3	122.4 (3)	O1—C11—H11B	110.1
N3—C4—C3	120.5 (3)	C10—C11—H11B	110.1
N3—C5—C6	109.8 (3)	H11A—C11—H11B	108.4
N3—C5—H5A	109.7	O1—C12—C17	124.1 (3)
C6—C5—H5A	109.7	O1—C12—C13	115.9 (3)
N3—C5—H5B	109.7	C17—C12—C13	120.0 (3)
C6—C5—H5B	109.7	C14—C13—C12	120.3 (3)
H5A—C5—H5B	108.2	C14—C13—H13	119.8
N4—C6—C5	112.1 (3)	C12—C13—H13	119.8
N4—C6—H6A	109.2	C15—C14—C13	119.3 (3)
C5—C6—H6A	109.2	C15—C14—H14	120.4
N4—C6—H6B	109.2	C13—C14—H14	120.4
C5—C6—H6B	109.2	C14—C15—C16	121.2 (3)
H6A—C6—H6B	107.9	C14—C15—Cl2	119.6 (3)
N4—C7—C8	111.3 (3)	C16—C15—Cl2	119.3 (3)
N4—C7—H7A	109.4	C15—C16—C17	119.5 (4)
C8—C7—H7A	109.4	C15—C16—H16	120.3
N4—C7—H7B	109.4	C17—C16—H16	120.3
C8—C7—H7B	109.4	C12—C17—C16	119.8 (3)
H7A—C7—H7B	108.0	C12—C17—H17	120.1
N3—C8—C7	110.4 (3)	C16—C17—H17	120.1
N3—C8—H8A	109.6
C1—N1—N2—C4	−0.9 (5)	C4—N3—C8—C7	−160.2 (3)
N2—N1—C1—C2	2.5 (5)	C5—N3—C8—C7	56.0 (4)
N2—N1—C1—Cl1	−177.3 (2)	N4—C7—C8—N3	−57.3 (4)
N1—C1—C2—C3	−1.9 (5)	C7—N4—C9—C10	57.1 (4)
Cl1—C1—C2—C3	177.8 (2)	C6—N4—C9—C10	177.6 (3)
C1—C2—C3—C4	−0.2 (5)	N4—C9—C10—C11	172.0 (3)
N1—N2—C4—N3	−178.7 (3)	C12—O1—C11—C10	−175.1 (3)
N1—N2—C4—C3	−1.1 (5)	C9—C10—C11—O1	−71.7 (4)
C5—N3—C4—N2	0.0 (5)	C11—O1—C12—C17	−7.1 (5)
C8—N3—C4—N2	−141.5 (3)	C11—O1—C12—C13	173.0 (3)
C5—N3—C4—C3	−177.5 (3)	O1—C12—C13—C14	−178.8 (3)
C8—N3—C4—C3	41.0 (5)	C17—C12—C13—C14	1.3 (5)
C2—C3—C4—N2	1.6 (5)	C12—C13—C14—C15	−0.8 (5)
C2—C3—C4—N3	179.1 (3)	C13—C14—C15—C16	−0.5 (5)
C4—N3—C5—C6	160.3 (3)	C13—C14—C15—Cl2	179.6 (3)
C8—N3—C5—C6	−55.4 (4)	C14—C15—C16—C17	1.2 (5)
C9—N4—C6—C5	179.6 (3)	Cl2—C15—C16—C17	−178.9 (3)
C7—N4—C6—C5	−57.9 (4)	O1—C12—C17—C16	179.5 (3)
N3—C5—C6—N4	57.0 (4)	C13—C12—C17—C16	−0.6 (5)
C9—N4—C7—C8	178.2 (3)	C15—C16—C17—C12	−0.6 (5)
C6—N4—C7—C8	57.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.95	2.53	3.247 (6)	133
C3—H3···N2i	0.95	2.50	3.427 (6)	164
C13—H13···O1ii	0.95	2.60	3.529 (5)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.95	2.53	3.247 (6)	133
C3—H3⋯N2i	0.95	2.50	3.427 (6)	164
C13—H13⋯O1ii	0.95	2.60	3.529 (5)	168

Symmetry codes: (i) ; (ii) .