Crystal structure of 4-chloro-2-[(5-eth-oxy-1,3,4-thia-diazol-2-yl)meth-yl]-5-(piperidin-1-yl)pyridazin-3(2H)-one.

In the title mol-ecule, C14H18ClN5O2S, the six atoms of the 1,6-di-hydro-pyridazine ring are essentially coplanar (r.m.s. deviation = 0.008 Å), and the dihedral angle between this and the 1,3,4-thia-diazole ring is 62.06 (10)°. In the crystal, centrosymmetrically related mol-ecules are linked by inter-molecular C-H-O hydrogen bonding to form a supra-molecular dimer. The terminal ethyl group is statistically disordered over two positions.

Related literature

For the biological activity of pyridazinone derivatives, see: Abouzid et al. (2008 ▶); Siddiqui et al. (2010 ▶), and for their synthesis, see: Wang et al. (2010 ▶); Zhang et al. (2002 ▶).

Experimental

Crystal data

C14H18ClN5O2S

M = 355.84

Triclinic,

a = 5.2840 (8) Å

b = 11.0323 (16) Å

c = 14.902 (2) Å

α = 107.318 (2)°

β = 91.590 (2)°

γ = 99.528 (2)°

V = 815.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.30 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.895, T max = 0.942

4244 measured reflections

2828 independent reflections

2490 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.121

S = 1.58

2828 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) I. DOI: 10.1107/S1600536814020662/tk5340sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020662/tk5340Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814020662/tk5340Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814020662/tk5340fig1.tif

Mol­ecular structure of the title compound showing atom labelling and displacement ellipsoids at 50%.

CCDC reference: 1024313

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H18ClN5O2S	Z = 2
Mr = 355.84	F(000) = 372
Triclinic, P1	Dx = 1.450 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2840 (8) Å	Cell parameters from 2456 reflections
b = 11.0323 (16) Å	θ = 2.8–27.3°
c = 14.902 (2) Å	µ = 0.38 mm−1
α = 107.318 (2)°	T = 296 K
β = 91.590 (2)°	Block, yellow
γ = 99.528 (2)°	0.30 × 0.24 × 0.16 mm
V = 815.1 (2) Å3

Bruker APEXII CCD diffractometer	2828 independent reflections
Radiation source: fine-focus sealed tube	2490 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.895, Tmax = 0.942	k = −13→13
4244 measured reflections	l = −13→17

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) = 0.121	H-atom parameters constrained
S = 1.58	w = 1/[σ2(Fo2) + (0.0546P)2] where P = (Fo2 + 2Fc2)/3
2828 reflections	(Δ/σ)max = 0.050
229 parameters	Δρmax = 0.22 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	Occ. (<1)
C1	1.1293 (4)	0.40442 (18)	0.64144 (14)	0.0529 (5)
H1A	0.9963	0.4362	0.6807	0.064*
H1B	1.1620	0.4550	0.5984	0.064*
C2	1.3686 (5)	0.4198 (2)	0.70167 (19)	0.0710 (7)
H2A	1.4236	0.5100	0.7376	0.085*
H2B	1.5043	0.3928	0.6621	0.085*
C3	1.3239 (5)	0.3396 (2)	0.76876 (18)	0.0726 (7)
H3A	1.4850	0.3448	0.8038	0.087*
H3B	1.2037	0.3733	0.8135	0.087*
C4	1.2172 (5)	0.2004 (2)	0.71378 (17)	0.0623 (6)
H4A	1.3494	0.1633	0.6768	0.075*
H4B	1.1719	0.1521	0.7576	0.075*
C5	0.9873 (5)	0.1870 (2)	0.65010 (17)	0.0654 (6)
H5A	0.9358	0.0973	0.6122	0.079*
H5B	0.8461	0.2120	0.6873	0.079*
C6	0.8041 (4)	0.24108 (16)	0.34196 (13)	0.0418 (4)
C7	0.9639 (3)	0.28093 (16)	0.42889 (13)	0.0390 (4)
C8	0.8999 (4)	0.23463 (16)	0.50280 (13)	0.0426 (4)
C9	0.6649 (4)	0.14118 (19)	0.48425 (14)	0.0513 (5)
H9	0.6167	0.1065	0.5323	0.062*
C10	0.3987 (4)	0.1095 (2)	0.25530 (14)	0.0517 (5)
H10A	0.3853	0.1833	0.2340	0.062*
H10B	0.2307	0.0783	0.2729	0.062*
C11	0.4730 (4)	0.00539 (18)	0.17587 (13)	0.0452 (5)
C12	0.6399 (5)	−0.1324 (2)	0.05014 (15)	0.0605 (6)
C13A	0.6909 (17)	−0.3381 (7)	−0.0461 (7)	0.074 (2)	0.503 (13)
H13A	0.6744	−0.3654	0.0099	0.089*	0.503 (13)
H13B	0.5282	−0.3668	−0.0845	0.089*	0.503 (13)
C14A	0.9045 (12)	−0.3878 (6)	−0.1004 (7)	0.083 (3)	0.503 (13)
H14A	0.9387	−0.3461	−0.1480	0.125*	0.503 (13)
H14B	0.8561	−0.4794	−0.1298	0.125*	0.503 (13)
H14C	1.0565	−0.3701	−0.0584	0.125*	0.503 (13)
C13B	0.7259 (16)	−0.3012 (8)	−0.0838 (6)	0.071 (2)	0.497 (13)
H13C	0.8075	−0.3014	−0.1413	0.085*	0.497 (13)
H13D	0.5414	−0.3283	−0.0987	0.085*	0.497 (13)
C14B	0.8311 (17)	−0.3870 (7)	−0.0377 (8)	0.086 (3)	0.497 (13)
H14D	1.0040	−0.3483	−0.0114	0.129*	0.497 (13)
H14E	0.8312	−0.4692	−0.0836	0.129*	0.497 (13)
H14F	0.7260	−0.3987	0.0116	0.129*	0.497 (13)
Cl1	1.24862 (9)	0.38323 (4)	0.42952 (4)	0.0529 (2)
N1	1.0406 (3)	0.26824 (15)	0.58761 (11)	0.0507 (4)
N2	0.5837 (3)	0.15084 (14)	0.33835 (11)	0.0437 (4)
N3	0.5152 (3)	0.10080 (16)	0.40812 (12)	0.0519 (4)
N4	0.3405 (4)	−0.10968 (17)	0.14941 (13)	0.0585 (5)
N5	0.4391 (4)	−0.19254 (17)	0.07519 (14)	0.0630 (5)
O1	0.8484 (3)	0.27791 (13)	0.27325 (10)	0.0585 (4)
O2	0.7819 (4)	−0.1833 (2)	−0.01905 (13)	0.0901 (6)
S1	0.73552 (11)	0.02873 (5)	0.11291 (4)	0.0556 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0616 (13)	0.0406 (11)	0.0504 (12)	0.0058 (9)	−0.0067 (10)	0.0075 (9)
C2	0.0735 (16)	0.0530 (13)	0.0755 (16)	−0.0080 (11)	−0.0252 (13)	0.0164 (12)
C3	0.0772 (17)	0.0714 (15)	0.0639 (15)	0.0039 (12)	−0.0229 (13)	0.0205 (13)
C4	0.0673 (15)	0.0634 (14)	0.0622 (14)	0.0080 (11)	−0.0004 (11)	0.0307 (12)
C5	0.0680 (15)	0.0626 (14)	0.0651 (14)	−0.0112 (11)	−0.0107 (12)	0.0326 (12)
C6	0.0471 (11)	0.0336 (9)	0.0436 (11)	0.0097 (8)	0.0044 (8)	0.0091 (8)
C7	0.0404 (10)	0.0292 (8)	0.0459 (10)	0.0035 (7)	0.0023 (8)	0.0109 (7)
C8	0.0475 (11)	0.0324 (9)	0.0443 (11)	0.0013 (7)	−0.0012 (8)	0.0102 (8)
C9	0.0562 (13)	0.0474 (11)	0.0436 (11)	−0.0099 (9)	−0.0005 (9)	0.0145 (9)
C10	0.0438 (11)	0.0568 (12)	0.0496 (12)	0.0116 (9)	−0.0059 (9)	0.0085 (9)
C11	0.0427 (11)	0.0483 (11)	0.0413 (10)	0.0047 (8)	−0.0079 (8)	0.0117 (8)
C12	0.0638 (15)	0.0613 (13)	0.0476 (12)	0.0168 (11)	−0.0100 (11)	0.0022 (10)
C13A	0.088 (5)	0.058 (4)	0.058 (5)	0.008 (3)	0.015 (4)	−0.006 (3)
C14A	0.073 (4)	0.068 (4)	0.088 (6)	0.010 (3)	0.024 (4)	−0.007 (3)
C13B	0.080 (4)	0.073 (5)	0.045 (4)	0.009 (3)	−0.002 (3)	0.000 (3)
C14B	0.090 (6)	0.075 (4)	0.085 (6)	0.010 (4)	−0.001 (5)	0.017 (4)
Cl1	0.0456 (3)	0.0449 (3)	0.0658 (4)	−0.0037 (2)	0.0049 (2)	0.0198 (2)
N1	0.0600 (11)	0.0404 (9)	0.0476 (10)	−0.0061 (7)	−0.0102 (8)	0.0170 (7)
N2	0.0423 (9)	0.0424 (8)	0.0409 (9)	0.0042 (7)	−0.0018 (7)	0.0069 (7)
N3	0.0518 (10)	0.0487 (9)	0.0467 (10)	−0.0064 (7)	0.0007 (8)	0.0107 (8)
N4	0.0539 (11)	0.0553 (11)	0.0567 (11)	−0.0004 (8)	−0.0072 (9)	0.0092 (9)
N5	0.0615 (12)	0.0521 (11)	0.0610 (12)	0.0042 (9)	−0.0115 (10)	0.0007 (9)
O1	0.0772 (10)	0.0514 (8)	0.0479 (8)	0.0030 (7)	−0.0008 (7)	0.0220 (7)
O2	0.0843 (13)	0.0960 (14)	0.0663 (11)	0.0270 (11)	0.0062 (10)	−0.0163 (10)
S1	0.0575 (4)	0.0545 (3)	0.0502 (3)	0.0046 (2)	0.0026 (3)	0.0120 (2)

C1—N1	1.466 (2)	C10—N2	1.464 (2)
C1—C2	1.486 (3)	C10—C11	1.496 (3)
C1—H1A	0.9700	C10—H10A	0.9700
C1—H1B	0.9700	C10—H10B	0.9700
C2—C3	1.520 (3)	C11—N4	1.284 (3)
C2—H2A	0.9700	C11—S1	1.723 (2)
C2—H2B	0.9700	C12—N5	1.282 (3)
C3—C4	1.512 (3)	C12—O2	1.334 (3)
C3—H3A	0.9700	C12—S1	1.725 (2)
C3—H3B	0.9700	C13A—C14A	1.491 (13)
C4—C5	1.480 (3)	C13A—O2	1.619 (8)
C4—H4A	0.9700	C13A—H13A	0.9700
C4—H4B	0.9700	C13A—H13B	0.9700
C5—N1	1.476 (2)	C14A—H14A	0.9600
C5—H5A	0.9700	C14A—H14B	0.9600
C5—H5B	0.9700	C14A—H14C	0.9600
C6—O1	1.224 (2)	C13B—O2	1.349 (7)
C6—N2	1.390 (2)	C13B—C14B	1.489 (14)
C6—C7	1.436 (3)	C13B—H13C	0.9700
C7—C8	1.374 (3)	C13B—H13D	0.9700
C7—Cl1	1.7228 (18)	C14B—H14D	0.9600
C8—N1	1.366 (2)	C14B—H14E	0.9600
C8—C9	1.438 (3)	C14B—H14F	0.9600
C9—N3	1.282 (3)	N2—N3	1.347 (2)
C9—H9	0.9300	N4—N5	1.385 (3)
N1—C1—C2	110.36 (17)	N2—C10—H10A	109.0
N1—C1—H1A	109.6	C11—C10—H10A	109.0
C2—C1—H1A	109.6	N2—C10—H10B	109.0
N1—C1—H1B	109.6	C11—C10—H10B	109.0
C2—C1—H1B	109.6	H10A—C10—H10B	107.8
H1A—C1—H1B	108.1	N4—C11—C10	121.30 (19)
C1—C2—C3	110.7 (2)	N4—C11—S1	114.96 (16)
C1—C2—H2A	109.5	C10—C11—S1	123.74 (14)
C3—C2—H2A	109.5	N5—C12—O2	126.0 (2)
C1—C2—H2B	109.5	N5—C12—S1	116.59 (17)
C3—C2—H2B	109.5	O2—C12—S1	117.4 (2)
H2A—C2—H2B	108.1	C14A—C13A—O2	102.4 (7)
C4—C3—C2	109.89 (19)	C14A—C13A—H13A	111.3
C4—C3—H3A	109.7	O2—C13A—H13A	111.3
C2—C3—H3A	109.7	C14A—C13A—H13B	111.3
C4—C3—H3B	109.7	O2—C13A—H13B	111.3
C2—C3—H3B	109.7	H13A—C13A—H13B	109.2
H3A—C3—H3B	108.2	O2—C13B—C14B	104.2 (7)
C5—C4—C3	112.46 (19)	O2—C13B—H13C	110.9
C5—C4—H4A	109.1	C14B—C13B—H13C	110.9
C3—C4—H4A	109.1	O2—C13B—H13D	110.9
C5—C4—H4B	109.1	C14B—C13B—H13D	110.9
C3—C4—H4B	109.1	H13C—C13B—H13D	108.9
H4A—C4—H4B	107.8	C13B—C14B—H14D	109.5
N1—C5—C4	111.07 (17)	C13B—C14B—H14E	109.5
N1—C5—H5A	109.4	H14D—C14B—H14E	109.5
C4—C5—H5A	109.4	C13B—C14B—H14F	109.5
N1—C5—H5B	109.4	H14D—C14B—H14F	109.5
C4—C5—H5B	109.4	H14E—C14B—H14F	109.5
H5A—C5—H5B	108.0	C8—N1—C1	120.60 (15)
O1—C6—N2	119.39 (17)	C8—N1—C5	119.35 (15)
O1—C6—C7	125.93 (18)	C1—N1—C5	111.72 (16)
N2—C6—C7	114.67 (16)	N3—N2—C6	125.32 (15)
C8—C7—C6	122.23 (17)	N3—N2—C10	115.33 (15)
C8—C7—Cl1	123.29 (14)	C6—N2—C10	119.26 (16)
C6—C7—Cl1	114.37 (14)	C9—N3—N2	116.97 (16)
N1—C8—C7	125.69 (17)	C11—N4—N5	113.00 (19)
N1—C8—C9	120.06 (17)	C12—N5—N4	110.34 (17)
C7—C8—C9	114.23 (17)	C12—O2—C13B	127.2 (5)
N3—C9—C8	126.57 (19)	C12—O2—C13A	105.7 (4)
N3—C9—H9	116.7	C13B—O2—C13A	29.3 (3)
C8—C9—H9	116.7	C11—S1—C12	85.12 (11)
N2—C10—C11	112.73 (15)
N1—C1—C2—C3	−58.3 (3)	C7—C6—N2—N3	−0.2 (3)
C1—C2—C3—C4	54.5 (3)	O1—C6—N2—C10	−4.9 (3)
C2—C3—C4—C5	−52.6 (3)	C7—C6—N2—C10	176.21 (15)
C3—C4—C5—N1	53.7 (3)	C11—C10—N2—N3	−100.33 (19)
O1—C6—C7—C8	−179.95 (18)	C11—C10—N2—C6	82.9 (2)
N2—C6—C7—C8	−1.1 (3)	C8—C9—N3—N2	−0.1 (3)
O1—C6—C7—Cl1	−3.6 (2)	C6—N2—N3—C9	0.8 (3)
N2—C6—C7—Cl1	175.26 (12)	C10—N2—N3—C9	−175.75 (18)
C6—C7—C8—N1	−179.63 (17)	C10—C11—N4—N5	−179.86 (16)
Cl1—C7—C8—N1	4.3 (3)	S1—C11—N4—N5	0.5 (2)
C6—C7—C8—C9	1.6 (3)	O2—C12—N5—N4	180.0 (2)
Cl1—C7—C8—C9	−174.41 (14)	S1—C12—N5—N4	0.7 (2)
N1—C8—C9—N3	−179.9 (2)	C11—N4—N5—C12	−0.8 (3)
C7—C8—C9—N3	−1.0 (3)	N5—C12—O2—C13B	9.5 (7)
N2—C10—C11—N4	112.2 (2)	S1—C12—O2—C13B	−171.2 (5)
N2—C10—C11—S1	−68.2 (2)	N5—C12—O2—C13A	−13.1 (5)
C7—C8—N1—C1	50.6 (3)	S1—C12—O2—C13A	166.2 (4)
C9—C8—N1—C1	−130.8 (2)	C14B—C13B—O2—C12	−87.8 (7)
C7—C8—N1—C5	−163.8 (2)	C14B—C13B—O2—C13A	−38.9 (11)
C9—C8—N1—C5	14.9 (3)	C14A—C13A—O2—C12	−163.5 (7)
C2—C1—N1—C8	−152.6 (2)	C14A—C13A—O2—C13B	55.1 (11)
C2—C1—N1—C5	59.4 (2)	N4—C11—S1—C12	−0.12 (17)
C4—C5—N1—C8	154.6 (2)	C10—C11—S1—C12	−179.72 (17)
C4—C5—N1—C1	−56.8 (3)	N5—C12—S1—C11	−0.36 (18)
O1—C6—N2—N3	178.74 (16)	O2—C12—S1—C11	−179.71 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14A—H14A···O1i	0.96	2.45	3.366 (11)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14A—H14A⋯O1i	0.96	2.45	3.366 (11)	160

Symmetry code: (i) .