


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015006301/tk5363sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015006301/tk5363Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015006301/tk5363Isup3.cml |
CCDC reference: 1056731
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.114
- Data-to-parameter ratio = 19.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT213_ALERT_2_B Atom C17B has ADP max/min Ratio ..... 4.4 prolat
Alert level C PLAT213_ALERT_2_C Atom C18A has ADP max/min Ratio ..... 3.1 prolat PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 5.5 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) ... 6.0 Ratio PLAT234_ALERT_4_C Large Hirshfeld Difference C17A -- C18A .. 0.17 Ang. PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... O4 Check PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.1 Note
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT300_ALERT_4_G Atom Site Occupancy of *O3A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *O3B is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of >C17A is Constrained at 0.570 Check PLAT300_ALERT_4_G Atom Site Occupancy of >C18A is Constrained at 0.570 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C17B is Constrained at 0.430 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C18B is Constrained at 0.430 Check PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 12 Note PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C14 Check PLAT431_ALERT_2_G Short Inter HL..A Contact Cl1 .. O2 .. 3.08 Ang. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 55 Check O3A -C16 -O3B 1.555 1.555 1.555 24.80 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 92 Check C17A -O4 -C17B 1.555 1.555 1.555 17.90 Deg. PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by . 1 Units
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 11 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
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).
The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and C—H = 0.96 Å (methyl), and with Uiso(H) = 1.2 Ueq (aromatic and methylene) and Uiso(H) = 1.5 Ueq for methyl. This structure is characterized by a partial disorder at the acetate group, with the ethyl group split into two parts. The major component had a site occupancy factor = 0.57 (3). The carbonyl-O3 was statistically disordered. Owing to poor agreement, the (0 0 2) reflection was omitted from the final cycles of refinement.
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.
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).
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).
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) |
C18H17ClN2O4 | V = 1759.06 (7) Å3 |
Mr = 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 |
Bruker APEXII CCD diffractometer | 4925 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3350 reflections with I > 2σ(I) |
Tmin = 0.589, Tmax = 0.746 | Rint = 0.031 |
12689 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.114 | Δρmax = 0.25 e Å−3 |
S = 1.02 | Δρmin = −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 |
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 |
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. |
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. |
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.