Crystal structure of 4-chloro-2-[(5-eth­oxy-1,3,4-thia­diazol-2-yl)meth­yl]-5-(piperidin-1-yl)pyridazin-3(2H)-one

Li, H.; Ren, X.; Li, Y.; Zhao, L.

doi:10.1107/S1600536814020662

organic compounds

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Volume 70| Part 10| October 2014| Page o1113

doi:10.1107/S1600536814020662

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Crystal structure of 4-chloro-2-[(5-ethoxy-1,3,4-thiadiazol-2-yl)methyl]-5-(piperidin-1-yl)pyridazin-3(2H)-one

Hongsen Li,^a ^* Xinfeng Ren,^a Ya Li ^a and Linjing Zhao ^a

^aCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, People's Republic of China
^*Correspondence e-mail: lihongsen19@163.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 1 September 2014; accepted 15 September 2014; online 20 September 2014)

In the title molecule, C₁₄H₁₈ClN₅O₂S, the six atoms of the 1,6-dihydropyridazine ring are essentially coplanar (r.m.s. deviation = 0.008 Å), and the dihedral angle between this and the 1,3,4-thiadiazole ring is 62.06 (10)°. In the crystal, centrosymmetrically related molecules are linked by intermolecular C—H—O hydrogen bonding to form a supramolecular dimer. The terminal ethyl group is statistically disordered over two positions.

Keywords: pyridazinone derivatives; crystal structure; C—H—O hydrogen bonding.

CCDC reference: 1024313

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₈ClN₅O₂S
M_r = 355.84
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.121
S = 1.58
2828 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) -x+2, -y, -z.

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.

Supporting information

CCDC reference: 1024313

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814020662/tk5340sup1.cif

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

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

checkCIF report

Experimental top

A mixture of 4,5-dichloro-2-[(5-ethoxy-1,3,4-thiadiazol-2-yl)methyl]-pyridazin-3(2H)-one (3.98 g, 1.3 mmol), piperidine (1.37 g, 19.5 mmol), potassium carbonate (3 g) and dry DMF (30mL) was stirred at 40^oC for 8 h. The mixture was then poured into ice-water and a yellow precipitate -formed. The precipitate was washed with water, followed by vaccum drying, to give the pure title compound (3.38 g, yield: 73.2 %). The obtained compound was recrystallized from its ethyl acetate/petroleum ether (5:1) to give yellow crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C). The terminal ethyl group (C13 and C14) was statistically disordered over two positions.

Related literature top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing atom labelling and displacement ellipsoids at 50%.

4-Chloro-2-[(5-ethoxy-1,3,4-thiadiazol-2-yl)methyl]-5-(piperidin-1-yl)pyridazin-3(2H)-one top

Crystal data top

C₁₄H₁₈ClN₅O₂S	Z = 2
M_r = 355.84	F(000) = 372
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0546P)²] where P = (F_o² + 2F_c²)/3
2828 reflections	(Δ/σ)_max = 0.050
229 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₈ClN₅O₂S	γ = 99.528 (2)°
M_r = 355.84	V = 815.1 (2) Å³
Triclinic, P1	Z = 2
a = 5.2840 (8) Å	Mo Kα radiation
b = 11.0323 (16) Å	µ = 0.38 mm⁻¹
c = 14.902 (2) Å	T = 296 K
α = 107.318 (2)°	0.30 × 0.24 × 0.16 mm
β = 91.590 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2828 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2490 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.942	R_int = 0.012
4244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.58	Δρ_max = 0.22 e Å⁻³
2828 reflections	Δρ_min = −0.23 e Å⁻³
229 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z.

Acknowledgements

Financial support from the Development Program of the Shanghai University of Engineering Science is gratefully acknowledged.

References

Abouzid, K., Hakeem, M. A., Khalil, O. & Maklad, Y. (2008). Bioorg. Med. Chem. 16, 382–389. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Gοttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 70| Part 10| October 2014| Page o1113

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4-chloro-2-[(5-eth­­oxy-1,3,4-thia­diazol-2-yl)meth­yl]-5-(piperidin-1-yl)pyridazin-3(2H)-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4-chloro-2-[(5-ethoxy-1,3,4-thiadiazol-2-yl)methyl]-5-(piperidin-1-yl)pyridazin-3(2H)-one