4-Chloro-5-(di­methyl­amino)-2-[(5-phenyl-1,3,4-oxa­diazol-2-yl)meth­yl]pyridazin-3(2H)-one

Song, J.; Jiang, X.; Wang, Z.; Pei, J.; Li, H.

doi:10.1107/S241431462200342X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 3| March 2022| x220342

https://doi.org/10.1107/S241431462200342X

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4-Chloro-5-(dimethylamino)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one

Jingjing Song,^a Xinyu Jiang,^a Ziyi Wang,^a Jingyao Pei ^a and Hongsen Li ^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 L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 9 March 2022; accepted 26 March 2022; online 31 March 2022)

In the structure of the title compound, C₁₅H₁₄ClN₅O₂, the terminal phenyl ring and the adjacent furan ring subtend a dihedral angle of 6.77 (17)°. The 4-chloro-5-(dimethylamino)-pyridazin-3(2H)-one group is linked to the oxadiazole ring by a methylene bridge, and the dihedral angle between the pyridazine and oxadiazole rings is 88.66 (14)°. In the crystal, C—H⋯O and C—H⋯N hydrogen bonds extend the structure into a three-dimensional network.

Keywords: crystal structure; pyridazinone; oxadiazole; hydrogen bonding.

CCDC reference: 2162169

Structure description

Pyridazinones have attracted increasing attention as a scaffold because of their wide spectrum of biological activity (Zou et al., 2002 ). Along with the development of design and synthetic methodology, pyridazinone derivatives have been widely applied in medicinal and agricultural chemistry (Arora et al., 2022 ; Vaidergorn et al., 2021 ; Zhang et al., 2020 ; Lu et al., 2017 ; Cao et al., 2005 ; Xu et al., 2008 ; Sun et al., 2015 ). As part of our work in this area, a series of pyridazinone derivatives containing an oxadiazole moiety have been designed and synthesized, and we report here the crystal structure of the tittle compound.

The molecular structure of the title compound is shown in Fig. 1. The phenyl (C1–C6) and oxadiazole (O1/N1/N2/C7/C8) rings are almost coplanar, subtending a dihedral angle of 6.77 (17)°. The pyridazine ring is almost perpendicular to oxadiazole ring, making a dihedral angle of 88.66 (14)°. The dihedral angle between the phenyl and pyridazine rings is 82.01 (17)°.

Figure 1
The molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

The crystal packing is characterized by C—H⋯N and C—H⋯O contacts (Fig. 2, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.36	3.125 (5)	140
C1—H1⋯N5ⁱⁱ	0.93	2.61	3.477 (5)	156
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) .

Figure 2
The crystal packing of the title compound. The C—H⋯N and C—H⋯O hydrogen bonds are shown as dashed lines (see also Table 1

Synthesis and crystallization

To a 100 ml round-bottom flask, 4,5-dichloro-2-[(5-phenyl-1,3,4-oxadiazol-2-yl) methyl]pyridazin-3(2H)-one (1.0 g, 3.1 mmol), dimethylamine (0.6 ml, 6.2 mmol), and potassium carbonate (0.86 g, 6.2 mmol) were added in 30 ml of DMF and stirred for 8 h at 353 K. Afterwards, the reaction mixture was cooled and poured into 60 ml of ice–water. The precipitate formed was collected by filtration and then dried to obtain the pure title compound (yield 0.56 g, 54.6%). It was recrystallized from mixed solvents of ethyl acetate and petroleum (3:5) to give crystals suitable for X-ray diffraction (m.p. 427–429 K).

¹H NMR (400 MHz, CDCl₃): 3.18 (s, 6H), 5.62 (s, 2H), 7.54 (m, 3H), 7.67 (s, 1H), 8.06 (dd, 2H, J = 7.6 Hz, J = 1.6 Hz). IR (KBr, cm⁻¹): 2973, 2937, 1632, 1600, 1520, 1482, 1449, 1216, 1146, 752, 710.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClN₅O₂
M_r	331.76
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	7.1533 (16), 11.936 (3), 9.004 (2)
β (°)	98.128 (5)
V (Å³)	761.1 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.27
Crystal size (mm)	0.22 × 0.17 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002 )
T_min, T_max	0.580, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	4542, 2915, 2673
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.100, 1.04
No. of reflections	2915
No. of parameters	211
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30
Absolute structure	Flack x determined using 1139 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.00 (4)
Computer programs: SMART and SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008 ) and SHELXL2013 (Sheldrick, 2015 ).

Structural data

CCDC reference: 2162169

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431462200342X/vm4052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462200342X/vm4052Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431462200342X/vm4052Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-Chloro-5-(dimethylamino)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one top

Crystal data top

C₁₅H₁₄ClN₅O₂	F(000) = 344
M_r = 331.76	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.1533 (16) Å	Cell parameters from 2107 reflections
b = 11.936 (3) Å	θ = 5.7–49.7°
c = 9.004 (2) Å	µ = 0.27 mm⁻¹
β = 98.128 (5)°	T = 293 K
V = 761.1 (3) Å³	Prismatic, colorless
Z = 2	0.22 × 0.17 × 0.12 mm

Data collection top

Bruker SMART CCD area detector diffractometer	2673 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.030
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θ_max = 26.0°, θ_min = 2.3°
T_min = 0.580, T_max = 0.746	h = −8→8
4542 measured reflections	k = −14→14
2915 independent reflections	l = −9→11

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0624P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.042	(Δ/σ)_max < 0.001
wR(F²) = 0.100	Δρ_max = 0.28 e Å⁻³
S = 1.04	Δρ_min = −0.30 e Å⁻³
2915 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
211 parameters	Extinction coefficient: 0.029 (8)
1 restraint	Absolute structure: Flack x determined using 1139 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.00 (4)

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.85200 (15)	0.73449 (8)	0.58094 (11)	0.0698 (3)
N1	0.3672 (4)	1.1087 (2)	0.1248 (3)	0.0522 (7)
N2	0.5386 (4)	1.0502 (2)	0.1672 (3)	0.0525 (7)
N3	0.8278 (4)	0.8804 (2)	0.1888 (3)	0.0450 (6)
N4	0.9890 (4)	0.9391 (2)	0.1928 (3)	0.0503 (7)
N5	1.2442 (4)	0.8512 (2)	0.5493 (3)	0.0501 (7)
O1	0.3908 (3)	0.97490 (18)	−0.0393 (2)	0.0446 (5)
O2	0.6230 (4)	0.7702 (2)	0.2898 (3)	0.0695 (8)
C1	0.0415 (5)	1.0303 (3)	−0.2139 (4)	0.0530 (8)
H1	0.1196	0.9776	−0.2501	0.064*
C2	−0.1339 (5)	1.0519 (4)	−0.2928 (4)	0.0629 (10)
H2	−0.1736	1.0139	−0.3818	0.075*
C3	−0.2509 (5)	1.1296 (3)	−0.2406 (5)	0.0619 (10)
H3	−0.3693	1.1446	−0.2939	0.074*
C4	−0.1906 (6)	1.1849 (3)	−0.1086 (5)	0.0605 (9)
H4	−0.2695	1.2372	−0.0726	0.073*
C5	−0.0155 (5)	1.1641 (3)	−0.0288 (4)	0.0526 (8)
H5	0.0237	1.2023	0.0601	0.063*
C6	0.1024 (4)	1.0857 (3)	−0.0819 (3)	0.0425 (7)
C7	0.2862 (4)	1.0612 (2)	0.0054 (3)	0.0406 (7)
C8	0.5443 (4)	0.9750 (3)	0.0679 (3)	0.0422 (7)
C9	0.6961 (5)	0.8919 (3)	0.0516 (4)	0.0502 (8)
H9A	0.6391	0.8196	0.0245	0.060*
H9B	0.7642	0.9154	−0.0289	0.060*
C10	0.7789 (4)	0.8150 (3)	0.3034 (4)	0.0453 (7)
C11	0.9230 (5)	0.8076 (3)	0.4331 (3)	0.0449 (7)
C12	1.0946 (4)	0.8589 (3)	0.4373 (3)	0.0396 (6)
C13	1.1132 (5)	0.9282 (3)	0.3105 (4)	0.0473 (8)
H13	1.2245	0.9690	0.3132	0.057*
C14	1.2910 (6)	0.7498 (4)	0.6345 (4)	0.0692 (11)
H14A	1.2811	0.7631	0.7382	0.104*
H14B	1.4178	0.7277	0.6249	0.104*
H14C	1.2052	0.6912	0.5968	0.104*
C15	1.4001 (5)	0.9309 (4)	0.5556 (4)	0.0636 (10)
H15A	1.4852	0.9073	0.4882	0.095*
H15B	1.4664	0.9339	0.6559	0.095*
H15C	1.3513	1.0038	0.5266	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0676 (6)	0.0740 (6)	0.0695 (6)	−0.0110 (5)	0.0159 (4)	0.0263 (5)
N1	0.0468 (16)	0.0478 (15)	0.0600 (17)	0.0006 (13)	0.0010 (13)	−0.0103 (13)
N2	0.0476 (16)	0.0503 (15)	0.0563 (15)	−0.0009 (13)	−0.0047 (12)	−0.0085 (14)
N3	0.0368 (14)	0.0436 (14)	0.0518 (14)	0.0001 (11)	−0.0033 (11)	0.0016 (12)
N4	0.0466 (15)	0.0496 (15)	0.0525 (15)	−0.0048 (12)	−0.0002 (13)	0.0126 (12)
N5	0.0424 (15)	0.0559 (15)	0.0498 (15)	0.0020 (12)	−0.0017 (12)	0.0040 (12)
O1	0.0411 (12)	0.0456 (11)	0.0444 (11)	0.0056 (10)	−0.0034 (9)	−0.0044 (9)
O2	0.0435 (14)	0.0800 (19)	0.0831 (17)	−0.0224 (13)	0.0021 (12)	0.0027 (14)
C1	0.0453 (19)	0.057 (2)	0.0552 (19)	0.0100 (16)	0.0037 (15)	−0.0011 (16)
C2	0.050 (2)	0.070 (2)	0.066 (2)	0.0062 (18)	−0.0032 (17)	0.0008 (19)
C3	0.0411 (19)	0.063 (2)	0.079 (3)	0.0094 (17)	0.0004 (17)	0.0143 (19)
C4	0.051 (2)	0.0516 (19)	0.083 (3)	0.0150 (17)	0.0229 (18)	0.0122 (18)
C5	0.054 (2)	0.0462 (18)	0.0600 (19)	0.0089 (15)	0.0150 (16)	0.0052 (14)
C6	0.0381 (16)	0.0404 (15)	0.0499 (16)	0.0022 (13)	0.0093 (13)	0.0089 (12)
C7	0.0404 (15)	0.0377 (15)	0.0444 (15)	0.0012 (13)	0.0085 (13)	0.0039 (13)
C8	0.0393 (16)	0.0423 (15)	0.0428 (15)	−0.0037 (13)	−0.0015 (12)	−0.0004 (13)
C9	0.0467 (18)	0.0508 (19)	0.0503 (17)	0.0055 (15)	−0.0028 (14)	−0.0043 (15)
C10	0.0389 (17)	0.0411 (15)	0.0557 (18)	−0.0027 (13)	0.0060 (14)	0.0000 (14)
C11	0.0470 (18)	0.0407 (15)	0.0478 (16)	0.0018 (14)	0.0099 (14)	0.0076 (13)
C12	0.0362 (15)	0.0386 (14)	0.0433 (15)	0.0041 (12)	0.0034 (12)	−0.0002 (12)
C13	0.0387 (17)	0.0497 (17)	0.0526 (18)	−0.0100 (14)	0.0033 (15)	0.0062 (15)
C14	0.068 (3)	0.071 (2)	0.064 (2)	0.015 (2)	−0.0101 (18)	0.013 (2)
C15	0.0431 (19)	0.085 (3)	0.060 (2)	−0.0084 (19)	−0.0026 (16)	−0.0018 (19)

Geometric parameters (Å, º) top

Cl1—C11	1.727 (3)	C3—H3	0.9300
N1—C7	1.279 (4)	C4—C5	1.376 (6)
N1—N2	1.415 (4)	C4—H4	0.9300
N2—C8	1.272 (4)	C5—C6	1.389 (5)
N3—N4	1.345 (4)	C5—H5	0.9300
N3—C10	1.378 (4)	C6—C7	1.462 (4)
N3—C9	1.450 (4)	C8—C9	1.494 (5)
N4—C13	1.290 (4)	C9—H9A	0.9700
N5—C12	1.366 (4)	C9—H9B	0.9700
N5—C14	1.447 (5)	C10—C11	1.447 (4)
N5—C15	1.461 (5)	C11—C12	1.367 (5)
O1—C8	1.355 (3)	C12—C13	1.432 (4)
O1—C7	1.367 (4)	C13—H13	0.9300
O2—C10	1.227 (4)	C14—H14A	0.9600
C1—C6	1.376 (5)	C14—H14B	0.9600
C1—C2	1.376 (5)	C14—H14C	0.9600
C1—H1	0.9300	C15—H15A	0.9600
C2—C3	1.376 (6)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.374 (6)

C7—N1—N2	106.3 (3)	N2—C8—C9	129.4 (3)
C8—N2—N1	105.7 (2)	O1—C8—C9	117.2 (3)
N4—N3—C10	125.6 (3)	N3—C9—C8	111.9 (3)
N4—N3—C9	115.2 (3)	N3—C9—H9A	109.2
C10—N3—C9	119.2 (3)	C8—C9—H9A	109.2
C13—N4—N3	117.3 (3)	N3—C9—H9B	109.2
C12—N5—C14	123.1 (3)	C8—C9—H9B	109.2
C12—N5—C15	119.9 (3)	H9A—C9—H9B	107.9
C14—N5—C15	114.0 (3)	O2—C10—N3	119.7 (3)
C8—O1—C7	102.2 (2)	O2—C10—C11	126.0 (3)
C6—C1—C2	120.7 (3)	N3—C10—C11	114.3 (3)
C6—C1—H1	119.7	C12—C11—C10	122.0 (3)
C2—C1—H1	119.7	C12—C11—Cl1	124.4 (2)
C3—C2—C1	120.3 (4)	C10—C11—Cl1	113.5 (2)
C3—C2—H2	119.9	N5—C12—C11	126.6 (3)
C1—C2—H2	119.9	N5—C12—C13	118.4 (3)
C4—C3—C2	119.2 (4)	C11—C12—C13	114.9 (3)
C4—C3—H3	120.4	N4—C13—C12	125.6 (3)
C2—C3—H3	120.4	N4—C13—H13	117.2
C3—C4—C5	121.1 (3)	C12—C13—H13	117.2
C3—C4—H4	119.5	N5—C14—H14A	109.5
C5—C4—H4	119.5	N5—C14—H14B	109.5
C4—C5—C6	119.6 (4)	H14A—C14—H14B	109.5
C4—C5—H5	120.2	N5—C14—H14C	109.5
C6—C5—H5	120.2	H14A—C14—H14C	109.5
C1—C6—C5	119.2 (3)	H14B—C14—H14C	109.5
C1—C6—C7	121.3 (3)	N5—C15—H15A	109.5
C5—C6—C7	119.5 (3)	N5—C15—H15B	109.5
N1—C7—O1	112.3 (3)	H15A—C15—H15B	109.5
N1—C7—C6	129.0 (3)	N5—C15—H15C	109.5
O1—C7—C6	118.7 (3)	H15A—C15—H15C	109.5
N2—C8—O1	113.4 (3)	H15B—C15—H15C	109.5

C7—N1—N2—C8	1.0 (4)	N4—N3—C9—C8	−98.6 (4)
C10—N3—N4—C13	4.2 (5)	C10—N3—C9—C8	79.8 (4)
C9—N3—N4—C13	−177.5 (3)	N2—C8—C9—N3	16.7 (5)
C6—C1—C2—C3	0.0 (6)	O1—C8—C9—N3	−165.6 (3)
C1—C2—C3—C4	−0.2 (6)	N4—N3—C10—O2	175.9 (3)
C2—C3—C4—C5	0.3 (6)	C9—N3—C10—O2	−2.2 (4)
C3—C4—C5—C6	−0.2 (5)	N4—N3—C10—C11	−3.3 (4)
C2—C1—C6—C5	0.1 (5)	C9—N3—C10—C11	178.6 (3)
C2—C1—C6—C7	178.2 (3)	O2—C10—C11—C12	178.8 (3)
C4—C5—C6—C1	0.0 (5)	N3—C10—C11—C12	−2.0 (4)
C4—C5—C6—C7	−178.1 (3)	O2—C10—C11—Cl1	−4.0 (4)
N2—N1—C7—O1	−0.9 (4)	N3—C10—C11—Cl1	175.2 (2)
N2—N1—C7—C6	177.5 (3)	C14—N5—C12—C11	35.7 (5)
C8—O1—C7—N1	0.5 (3)	C15—N5—C12—C11	−165.2 (3)
C8—O1—C7—C6	−178.1 (3)	C14—N5—C12—C13	−145.3 (3)
C1—C6—C7—N1	176.0 (3)	C15—N5—C12—C13	13.8 (5)
C5—C6—C7—N1	−5.9 (5)	C10—C11—C12—N5	−175.4 (3)
C1—C6—C7—O1	−5.7 (4)	Cl1—C11—C12—N5	7.8 (5)
C5—C6—C7—O1	172.5 (3)	C10—C11—C12—C13	5.6 (4)
N1—N2—C8—O1	−0.7 (4)	Cl1—C11—C12—C13	−171.3 (2)
N1—N2—C8—C9	177.1 (3)	N3—N4—C13—C12	0.1 (5)
C7—O1—C8—N2	0.2 (4)	N5—C12—C13—N4	176.0 (3)
C7—O1—C8—C9	−177.9 (3)	C11—C12—C13—N4	−4.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14C···Cl1	0.96	2.56	3.114 (4)	117
C1—H1···O1	0.93	2.52	2.836 (4)	100
C3—H3···O2ⁱ	0.93	2.36	3.125 (5)	140
C1—H1···N5ⁱⁱ	0.93	2.61	3.477 (5)	156

Symmetry codes: (i) −x, y+1/2, −z; (ii) x−1, y, z−1.

Funding information

Financial support by the Students Innovation Program of Shanghai University of Engineering Science (cs2104005) is gratefully acknowledged.

References

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