Crystal structure of ethyl 2-{4-[(5-chloro-1-benzo­furan-2-yl)meth­yl]-3-methyl-6-oxo-1,6-di­hydro­pyridazin-1-yl}acetate

Boukharsa, Y.; El Ammari, L.; Taoufik, J.; Saadi, M.; Ansar, M.

doi:10.1107/S2056989015006301

organic compounds

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o291-o292

https://doi.org/10.1107/S2056989015006301

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Crystal structure of ethyl 2-{4-[(5-chloro-1-benzofuran-2-yl)methyl]-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl}acetate

Youness Boukharsa,^a ^* Lahcen El Ammari,^b Jamal Taoufik,^a Mohamed Saadi ^b and M'hammed Ansar ^a

^aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, BP 6203, Rabat Institute, University Mohammed V, Rabat, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP. 1014, Rabat, Morocco
^*Correspondence e-mail: y_boukharsa@yahoo.fr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 19 March 2015; accepted 27 March 2015; online 9 April 2015)

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 interactions, forming a three-dimensional network.

Keywords: crystal structure; pyridazinone derivative; hydrogen bonding.

CCDC reference: 1056731

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₇ClN₂O₄
M_r = 360.79
Orthorhombic, P 2₁ 2₁ 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.02
4925 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 2104 Friedel pairs
Absolute structure parameter: 0.02 (7)

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 1056731

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006301/tk5363sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006301/tk5363Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015006301/tk5363Isup3.cml

checkCIF report

Comment top

During recent years, pyridazinones have been a subject of numerous recent studies (Boukharsa et al., 2014) owing to their wide spectrum of pharmacological activities such as antimicrobial (Nagle et al., 2014), anti-fungal (El-Hashash et al., 2014), analgesic & anti-inflammatory (Tiryaki et al., 2013), anticancer (Csókás et al., 2013), anti-tubercular (Asif et al., 2014) and anti-hypertensive activities (Garkani-Nejad & Poshteh-Shirani, 2013). It has also been reported that pyridazinone derivative have remarkable insecticidal (Cao et al., 2003) and herbicidal activities (Jamet & Piedallu, 1975). In continuation of this line of research (Taoufik et al., 1984; Benchat et al., 1998; Abourichaa et al., 2003), we have developed a new pyridazin-3(2H)-one derivative. It will be subjected to further pharmacological investigations, especially tests of anticancer activity. Compound (I) is stable at room temperature, and its structure has been determined by NMR (¹H and ¹³ C). In this paper we wish to report the crystal structure determination of the title compound possessing the biologically active pyridazinone ring.

The molecule of the title compound is build up from 5-chlorobenzofuran-2-yl linked, via –CH₂– group, to six-membered heterocyclic ring which is related to acetate group as shown in Fig. 1. The benzofuran system is virtually planar with the largest deviation from the mean plane being -0.014 (2) Å at C4, and makes dihedral angle of 73.33 (8)° with the mean plane through the oxopyridazin (C10–C13,N1,N2) ring. Non classical C—H···O hydrogen bonds link the molecules into a three-dimensional network.

Related literature top

For pharmacological activities, e.g. antimicrobial, of pyridazinones, 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 activities of pyridazinone derivative, e.g. as insecticides and herbicides, see: Cao et al. (2003); Jamet & Piedallu (1975). For new pyridazin-3(2H)-one derivatives, see: Taoufik et al. (1984); Benchat et al. (1998); Abourichaa et al. (2003).

Experimental top

To a solution of 5-((5-chlorobenzofuran-2-yl)methyl)-6-methylpyridazin-3(2H)-one (0.5 g, 1.82 mmol) dissolved in tetrahydrofuran (15 ml) was added ethyl 2-bromoacetate (0.30 ml, 2.73 mmol), potassium carbonate (0.5 g, 3.64 mmol) and a catalytic amount of tetra-n-butylammonium bromide (0.05 g, 0.15 mmol). The mixture was stirred at room temperature for 6 h, and monitored by thin layer chromatography. The compound was removed by filtration and the filtrate concentrated under vacuum. The solid obtained was crystallized from ethanol to afford colourless crystals (Yield = 77%; M.pt = 136.9 °C).

Structure description top

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

Figures top

	Fig. 1. 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.
	Fig. 2. Crystal packing in the structure of the title compound, showing molecules linked by C—H···O hydrogen bonds (dashed lines).

Ethyl 2-{4-[(5-chloro-1-benzofuran-2-yl)methyl]-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl}acetate top

Crystal data top

C₁₈H₁₇ClN₂O₄	F(000) = 752
M_r = 360.79	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0511P)² + 0.0996P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.043
4925 reflections	Δρ_max = 0.25 e Å⁻³
255 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₇ClN₂O₄	V = 1759.06 (7) Å³
M_r = 360.79	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.9792 (2) Å	µ = 0.24 mm⁻¹
b = 8.7460 (2) Å	T = 296 K
c = 25.2064 (6) Å	0.37 × 0.34 × 0.29 mm

Data collection top

Bruker APEXII CCD diffractometer	4925 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3350 reflections with I > 2σ(I)
T_min = 0.589, T_max = 0.746	R_int = 0.031
12689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.114	Δρ_max = 0.25 e Å⁻³
S = 1.02	Δρ_min = −0.34 e Å⁻³
4925 reflections	Absolute structure: Flack & Bernardinelli (2000), 2104 Friedel pairs
255 parameters	Absolute structure parameter: 0.02 (7)
0 restraints

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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements, and the University Mohammed V, Rabat, Morocco, for financial support.

References

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Volume 71| Part 5| May 2015| Pages o291-o292

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

Crystal structure of ethyl 2-{4-[(5-chloro-1-benzo­furan-2-yl)meth­yl]-3-methyl-6-oxo-1,6-di­hydro­pyridazin-1-yl}acetate

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 ethyl 2-{4-[(5-chloro-1-benzofuran-2-yl)methyl]-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl}acetate