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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814020662/tk5340sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814020662/tk5340Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814020662/tk5340Isup3.cml Supplementary material

CCDC reference: 1024313

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.039
wR factor = 0.121
Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         O2 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.596         55 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Degree
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O2     --  C13A    ..        8.8 su
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          9 Note
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         84 Check
              C13B -O2   -C13A    1.555   1.555   1.555             29.30 Deg.
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          80 %
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Report

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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.

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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

Supporting information

Key indicators

checkCIF/PLATON results

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