Crystal structure of ethyl 2-{4-[(5-chloro-1-benzo-furan-2-yl)meth-yl]-3-methyl-6-oxo-1,6-di-hydro-pyridazin-1-yl}acetate.

In the title compound, C18H17ClN2O4, the dihedral angle between the benzofuran ring system [maximum deviation 0.014 (2) Å] and the oxopyradizine ring is 73.33 (8)°. The structure is characterized by disorder of the ethyl group, which is split into two parts, with a major component of 0.57 (3), and the acetate carbonyl O atom, which is statistically disordered. In the crystal, the molecules are linked by C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For pharmacological activities of pyridazinones, e.g. anti­microbial, see: Boukharsa et al. (2014 ▸); Nagle et al. (2014 ▸); El-Hashash et al. (2014 ▸); Tiryaki et al. (2013 ▸); Csókás et al. (2013 ▸); Asif et al. (2014 ▸); Garkani-Nejad & Poshteh-Shirani (2013 ▸). For biological activities of pyridazinone derivatives and their applications, e.g. as insecticides and herbicides, see: Cao et al. (2003 ▸); Jamet & Piedallu (1975 ▸). For pyridazin-3(2H)-one derivatives, see: Taoufik et al. (1984 ▸); Benchat et al. (1998 ▸); Abourichaa et al. (2003 ▸).

Experimental

Crystal data

C18H17ClN2O4

M = 360.79

Orthorhombic,

a = 7.9792 (2) Å

b = 8.7460 (2) Å

c = 25.2064 (6) Å

V = 1759.06 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.37 × 0.34 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.589, T max = 0.746

12689 measured reflections

4925 independent reflections

3350 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 1.02

4925 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack & Bernardinelli (2000 ▸), 2104 Friedel pairs

Absolute structure parameter: 0.02 (7)

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: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006301/tk5363sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006301/tk5363Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006301/tk5363Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006301/tk5363fig1.tif

Mol­ecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.

. DOI: 10.1107/S2056989015006301/tk5363fig2.tif

Crystal packing in the structure of the title compound, showing mol­ecules linked by C—H⋯O hydrogen bonds (dashed lines).

CCDC reference: 1056731

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

C18H17ClN2O4	F(000) = 752
Mr = 360.79	Dx = 1.362 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ac 2ab	Cell parameters from 4925 reflections
a = 7.9792 (2) Å	θ = 2.5–29.6°
b = 8.7460 (2) Å	µ = 0.24 mm−1
c = 25.2064 (6) Å	T = 296 K
V = 1759.06 (7) Å3	Block, colourless
Z = 4	0.37 × 0.34 × 0.29 mm

Bruker APEXII CCD diffractometer	4925 independent reflections
Radiation source: fine-focus sealed tube	3350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 29.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→6
Tmin = 0.589, Tmax = 0.746	k = −12→11
12689 measured reflections	l = −35→34

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.0996P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.043
4925 reflections	Δρmax = 0.25 e Å−3
255 parameters	Δρmin = −0.34 e Å−3
0 restraints	Absolute structure: Flack & Bernardinelli (2000), 2104 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (7)

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	0.0331 (3)	0.7077 (3)	0.55647 (8)	0.0497 (5)
C2	−0.0495 (3)	0.7389 (3)	0.50905 (9)	0.0551 (6)
H2	−0.1006	0.8335	0.5042	0.066*
C3	−0.0561 (3)	0.6314 (3)	0.46924 (8)	0.0500 (5)
H3	−0.1101	0.6507	0.4372	0.060*
C4	0.0215 (2)	0.4935 (2)	0.47935 (7)	0.0408 (4)
C5	0.1023 (2)	0.4581 (2)	0.52669 (7)	0.0401 (5)
C6	0.1087 (3)	0.5691 (3)	0.56674 (8)	0.0493 (6)
H6	0.1618	0.5500	0.5989	0.059*
C7	0.1597 (3)	0.3032 (3)	0.52045 (8)	0.0448 (5)
H7	0.2188	0.2460	0.5453	0.054*
C8	0.1118 (3)	0.2568 (3)	0.47190 (8)	0.0431 (5)
C9	0.1316 (3)	0.1120 (3)	0.44154 (8)	0.0472 (5)
H9A	0.0220	0.0785	0.4297	0.057*
H9B	0.1755	0.0342	0.4652	0.057*
C10	0.2463 (2)	0.1236 (2)	0.39358 (7)	0.0368 (4)
C11	0.3432 (2)	0.2461 (2)	0.38377 (7)	0.0414 (4)
H11	0.3383	0.3299	0.4064	0.050*
C12	0.4547 (3)	0.2499 (2)	0.33859 (8)	0.0409 (4)
C13	0.2541 (2)	−0.0037 (3)	0.35783 (7)	0.0384 (4)
C14	0.1523 (3)	−0.1455 (3)	0.36636 (9)	0.0514 (5)
H14A	0.1751	−0.2173	0.3385	0.077*
H14B	0.0353	−0.1198	0.3662	0.077*
H14C	0.1812	−0.1902	0.3999	0.077*
C15	0.5492 (3)	0.1158 (3)	0.25914 (8)	0.0460 (5)
H15A	0.5611	0.2173	0.2441	0.055*
H15B	0.4950	0.0513	0.2329	0.055*
C16	0.7196 (3)	0.0523 (3)	0.27179 (9)	0.0570 (6)
C17A	0.9885 (15)	0.004 (2)	0.2313 (4)	0.090 (4)	0.57 (3)
H17A	1.0439	0.0692	0.2571	0.108*	0.57 (3)
H17B	0.9939	−0.0998	0.2446	0.108*	0.57 (3)
C18A	1.0731 (14)	0.0109 (18)	0.1866 (4)	0.115 (5)	0.57 (3)
H18A	1.1866	−0.0209	0.1927	0.173*	0.57 (3)
H18B	1.0723	0.1140	0.1735	0.173*	0.57 (3)
H18C	1.0220	−0.0555	0.1609	0.173*	0.57 (3)
C17B	0.967 (2)	−0.045 (3)	0.2318 (8)	0.136 (9)	0.43 (3)
H17C	1.0491	0.0111	0.2524	0.164*	0.43 (3)
H17D	0.9406	−0.1378	0.2511	0.164*	0.43 (3)
C18B	1.027 (3)	−0.078 (5)	0.1915 (11)	0.201 (15)	0.43 (3)
H18D	1.1232	−0.1419	0.1977	0.302*	0.43 (3)
H18E	1.0608	0.0124	0.1729	0.302*	0.43 (3)
H18F	0.9469	−0.1334	0.1705	0.302*	0.43 (3)
N1	0.3493 (2)	−0.0030 (2)	0.31573 (6)	0.0420 (4)
N2	0.4446 (2)	0.12399 (19)	0.30664 (6)	0.0407 (4)
O1	0.02722 (17)	0.37131 (17)	0.44539 (5)	0.0441 (3)
O2	0.5521 (2)	0.35450 (19)	0.32838 (6)	0.0604 (4)
O3A	0.776 (2)	0.037 (5)	0.3148 (7)	0.069 (5)	0.50 (10)
O3B	0.756 (4)	−0.019 (7)	0.3125 (11)	0.088 (6)	0.50 (10)
O4	0.8114 (2)	0.0497 (3)	0.22828 (6)	0.0776 (7)
Cl1	0.04000 (9)	0.85141 (8)	0.60423 (3)	0.0730 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0478 (12)	0.0520 (13)	0.0493 (11)	−0.0015 (11)	0.0142 (10)	−0.0084 (11)
C2	0.0546 (14)	0.0482 (12)	0.0626 (13)	0.0075 (12)	0.0102 (11)	0.0050 (12)
C3	0.0488 (12)	0.0569 (13)	0.0443 (10)	0.0067 (11)	0.0026 (9)	0.0085 (11)
C4	0.0382 (10)	0.0484 (11)	0.0358 (9)	−0.0006 (9)	0.0078 (8)	−0.0005 (9)
C5	0.0345 (10)	0.0498 (12)	0.0359 (9)	0.0013 (8)	0.0070 (8)	0.0022 (10)
C6	0.0447 (12)	0.0665 (15)	0.0367 (10)	−0.0003 (10)	0.0053 (9)	−0.0045 (11)
C7	0.0416 (11)	0.0528 (13)	0.0401 (10)	0.0069 (9)	0.0050 (9)	0.0063 (10)
C8	0.0390 (11)	0.0473 (12)	0.0430 (10)	0.0028 (9)	0.0124 (9)	0.0046 (10)
C9	0.0465 (12)	0.0468 (12)	0.0483 (11)	−0.0017 (10)	0.0151 (9)	−0.0004 (11)
C10	0.0324 (9)	0.0403 (11)	0.0377 (9)	0.0021 (8)	0.0025 (7)	−0.0010 (9)
C11	0.0407 (11)	0.0402 (11)	0.0433 (10)	−0.0007 (9)	0.0069 (8)	−0.0071 (9)
C12	0.0364 (10)	0.0396 (10)	0.0466 (10)	−0.0023 (9)	0.0049 (8)	−0.0003 (9)
C13	0.0342 (9)	0.0410 (11)	0.0400 (9)	−0.0008 (8)	−0.0001 (8)	−0.0031 (9)
C14	0.0514 (13)	0.0480 (13)	0.0549 (12)	−0.0116 (11)	0.0066 (10)	−0.0053 (12)
C15	0.0453 (11)	0.0537 (13)	0.0390 (10)	0.0022 (11)	0.0098 (9)	−0.0005 (10)
C16	0.0521 (13)	0.0725 (18)	0.0463 (12)	0.0110 (12)	0.0144 (11)	0.0093 (13)
C17A	0.061 (5)	0.144 (10)	0.064 (4)	0.038 (5)	−0.005 (4)	0.003 (6)
C18A	0.061 (5)	0.197 (12)	0.088 (6)	0.058 (6)	0.045 (4)	0.051 (8)
C17B	0.068 (7)	0.191 (18)	0.150 (13)	0.082 (9)	0.079 (8)	0.109 (12)
C18B	0.098 (14)	0.31 (4)	0.195 (19)	0.098 (18)	−0.032 (12)	−0.15 (2)
N1	0.0421 (9)	0.0420 (10)	0.0420 (9)	−0.0047 (7)	0.0043 (7)	−0.0046 (8)
N2	0.0385 (9)	0.0433 (9)	0.0403 (8)	−0.0028 (8)	0.0092 (7)	−0.0037 (8)
O1	0.0458 (8)	0.0520 (9)	0.0345 (6)	0.0025 (7)	0.0015 (6)	−0.0032 (7)
O2	0.0626 (10)	0.0545 (10)	0.0640 (9)	−0.0194 (9)	0.0233 (8)	−0.0068 (9)
O3A	0.063 (4)	0.096 (10)	0.047 (4)	0.021 (5)	0.006 (3)	0.022 (5)
O3B	0.086 (7)	0.110 (15)	0.069 (5)	0.038 (8)	0.029 (4)	0.046 (7)
O4	0.0519 (10)	0.1259 (19)	0.0549 (9)	0.0329 (11)	0.0193 (8)	0.0216 (11)
Cl1	0.0791 (5)	0.0674 (4)	0.0725 (4)	−0.0034 (4)	0.0133 (3)	−0.0271 (3)

C1—C6	1.378 (3)	C13—C14	1.498 (3)
C1—C2	1.392 (3)	C14—H14A	0.9600
C1—Cl1	1.742 (2)	C14—H14B	0.9600
C2—C3	1.376 (3)	C14—H14C	0.9600
C2—H2	0.9300	C15—N2	1.461 (2)
C3—C4	1.380 (3)	C15—C16	1.504 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—O1	1.370 (2)	C15—H15B	0.9700
C4—C5	1.391 (3)	C16—O3A	1.182 (17)
C5—C6	1.401 (3)	C16—O3B	1.234 (17)
C5—C7	1.439 (3)	C16—O4	1.319 (2)
C6—H6	0.9300	C17A—C18A	1.316 (15)
C7—C8	1.345 (3)	C17A—O4	1.470 (12)
C7—H7	0.9300	C17A—H17A	0.9700
C8—O1	1.380 (3)	C17A—H17B	0.9700
C8—C9	1.488 (3)	C18A—H18A	0.9600
C9—C10	1.520 (3)	C18A—H18B	0.9600
C9—H9A	0.9700	C18A—H18C	0.9600
C9—H9B	0.9700	C17B—C18B	1.16 (3)
C10—C11	1.344 (3)	C17B—O4	1.493 (18)
C10—C13	1.434 (3)	C17B—H17C	0.9700
C11—C12	1.446 (3)	C17B—H17D	0.9700
C11—H11	0.9300	C18B—H18D	0.9600
C12—O2	1.228 (2)	C18B—H18E	0.9600
C12—N2	1.367 (3)	C18B—H18F	0.9600
C13—N1	1.305 (2)	N1—N2	1.365 (2)
C6—C1—C2	122.8 (2)	H14A—C14—H14C	109.5
C6—C1—Cl1	119.41 (17)	H14B—C14—H14C	109.5
C2—C1—Cl1	117.82 (18)	N2—C15—C16	111.14 (17)
C3—C2—C1	120.7 (2)	N2—C15—H15A	109.4
C3—C2—H2	119.7	C16—C15—H15A	109.4
C1—C2—H2	119.7	N2—C15—H15B	109.4
C2—C3—C4	116.43 (19)	C16—C15—H15B	109.4
C2—C3—H3	121.8	H15A—C15—H15B	108.0
C4—C3—H3	121.8	O3A—C16—O3B	24.8 (15)
O1—C4—C3	125.54 (18)	O3A—C16—O4	123.2 (9)
O1—C4—C5	110.30 (18)	O3B—C16—O4	123.6 (10)
C3—C4—C5	124.13 (19)	O3A—C16—C15	125.6 (9)
C4—C5—C6	118.7 (2)	O3B—C16—C15	124.9 (11)
C4—C5—C7	105.27 (18)	O4—C16—C15	109.41 (19)
C6—C5—C7	136.0 (2)	C18A—C17A—O4	115.8 (9)
C1—C6—C5	117.23 (19)	C18A—C17A—H17A	108.3
C1—C6—H6	121.4	O4—C17A—H17A	108.3
C5—C6—H6	121.4	C18A—C17A—H17B	108.3
C8—C7—C5	107.06 (19)	O4—C17A—H17B	108.3
C8—C7—H7	126.5	H17A—C17A—H17B	107.4
C5—C7—H7	126.5	C17A—C18A—H18A	109.5
C7—C8—O1	111.11 (19)	C17A—C18A—H18B	109.5
C7—C8—C9	134.0 (2)	H18A—C18A—H18B	109.5
O1—C8—C9	114.88 (17)	C17A—C18A—H18C	109.5
C8—C9—C10	114.63 (18)	H18A—C18A—H18C	109.5
C8—C9—H9A	108.6	H18B—C18A—H18C	109.5
C10—C9—H9A	108.6	C18B—C17B—O4	115.6 (19)
C8—C9—H9B	108.6	C18B—C17B—H17C	108.3
C10—C9—H9B	108.6	O4—C17B—H17C	108.4
H9A—C9—H9B	107.6	C18B—C17B—H17D	108.5
C11—C10—C13	118.60 (17)	O4—C17B—H17D	108.4
C11—C10—C9	123.06 (18)	H17C—C17B—H17D	107.4
C13—C10—C9	118.33 (18)	C17B—C18B—H18D	109.4
C10—C11—C12	121.13 (18)	C17B—C18B—H18E	109.6
C10—C11—H11	119.4	H18D—C18B—H18E	109.5
C12—C11—H11	119.4	C17B—C18B—H18F	109.4
O2—C12—N2	120.95 (17)	H18D—C18B—H18F	109.5
O2—C12—C11	124.88 (19)	H18E—C18B—H18F	109.5
N2—C12—C11	114.17 (17)	C13—N1—N2	117.70 (16)
N1—C13—C10	122.17 (19)	N1—N2—C12	126.10 (15)
N1—C13—C14	115.89 (18)	N1—N2—C15	114.57 (16)
C10—C13—C14	121.94 (17)	C12—N2—C15	119.25 (16)
C13—C14—H14A	109.5	C4—O1—C8	106.25 (15)
C13—C14—H14B	109.5	C16—O4—C17A	119.7 (5)
H14A—C14—H14B	109.5	C16—O4—C17B	114.9 (7)
C13—C14—H14C	109.5	C17A—O4—C17B	17.9 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3Bi	0.93	2.37	3.291 (19)	170
C15—H15B···O2ii	0.97	2.34	3.278 (3)	161
C18A—H18A···O2iii	0.96	2.41	3.310 (10)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O3B i	0.93	2.37	3.291(19)	170
C15H15BO2ii	0.97	2.34	3.278(3)	161
C18AH18AO2iii	0.96	2.41	3.310(10)	156

Symmetry codes: (i) ; (ii) ; (iii) .