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The structure of the title compound, C18H13N3O, comprises a twisted mol­ecule, with the dihedral angle between the two ring systems being 72.4 (1)°. The phthalazin-1-one O atom has three C—H...O close contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015362/cf6200sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015362/cf6200Isup2.hkl
Contains datablock I

CCDC reference: 198328

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.179
  • Data-to-parameter ratio = 15.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The title compound, (I) (Fig. 1) was obtained, rather than the intermediate hydrazone, from the reaction of 8-hydrazinoquinoline dihydrochloride hydrate and 2-acetylbenzoic acid, as shown in the reaction scheme below.

The intended product, the (E)-1-ethanone 8-quinolylhydrozone derivative (for example, Lynch & McClenaghan, 2001a), might have been useful in the cyclization to the corresponding pyrrolo[3,2-h]quinoline (for example, Lynch & McClenaghan, 2001b). However, similar products to (I) have been reported for the reactions of phenylhydrazine with, respectively, 2-acetylbenzoic acid (Rowe & Peters, 1931), 2-acetylbenzonitrile (Helberger & Rebay, 1937), and 3-(2-carboxyphenyl)-3-oxo-propionic acid (Roser, 1885). In (I), the two rings are inclined at 72.4 (1)° and the phthalazin-1-one O atom has three C—H···O close contacts.

Experimental top

8-Hydrazinoquinoline dihydrochloride hydrate (0.03 mmol), 2-acetylbenzoic acid (0.03 mmol) and triethylamine (0.046 mmol) were refluxed in 1:5 aqueous ethanol for 80 min. A crystalline solid was collected following acidification with dilute acetic acid (yield 95%). Crystals were grown from an ethanol solution (m.p. 450–452 K).

Refinement top

All H atoms were included in the refinement, at calculated positions, as riding models, with C—H distances set to 0.95 (Ar—H) or 0.98 Å (CH3).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids.
4-Methyl-2-(8-quinolyl)phthalazin-1-one top
Crystal data top
C18H13N3OF(000) = 300
Mr = 287.31Dx = 1.385 Mg m3
Triclinic, P1Melting point: 450-452 K K
a = 7.9530 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4914 (6) ÅCell parameters from 6981 reflections
c = 10.8850 (7) Åθ = 2.9–27.5°
α = 77.060 (6)°µ = 0.09 mm1
β = 74.114 (5)°T = 150 K
γ = 86.277 (3)°Block, colourless
V = 689.05 (7) Å30.10 × 0.10 × 0.05 mm
Z = 2
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
3005 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode1507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
Detector resolution: 9.091 pixels mm-1θmax = 27.4°, θmin = 3.5°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1010
Tmin = 0.991, Tmax = 0.996l = 1214
9188 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0888P)2]
where P = (Fo2 + 2Fc2)/3
3005 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C18H13N3Oγ = 86.277 (3)°
Mr = 287.31V = 689.05 (7) Å3
Triclinic, P1Z = 2
a = 7.9530 (4) ÅMo Kα radiation
b = 8.4914 (6) ŵ = 0.09 mm1
c = 10.8850 (7) ÅT = 150 K
α = 77.060 (6)°0.10 × 0.10 × 0.05 mm
β = 74.114 (5)°
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
3005 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
1507 reflections with I > 2σ(I)
Tmin = 0.991, Tmax = 0.996Rint = 0.075
9188 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.179H-atom parameters constrained
S = 0.97Δρmax = 0.30 e Å3
3005 reflectionsΔρmin = 0.30 e Å3
200 parameters
Special details top

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.2975 (0.0050) x − 3.4761 (0.0081) y + 5.4080 (0.0099) z = 3.6597 (0.0102)

* −0.0005 (0.0018) C5 * 0.0046 (0.0018) C6 * −0.0015 (0.0018) C7 * −0.0055 (0.0017) C8 * 0.0093 (0.0017) C9 * −0.0064 (0.0017) C10

Rms deviation of fitted atoms = 0.0055

− 1.2600 (0.0077) x + 7.0085 (0.0047) y + 6.7598 (0.0084) z = 8.0017 (0.0067)

Angle to previous plane (with approximate e.s.d.) = 72.36 (0.08)

* 0.0135 (0.0016) C11 * −0.0070 (0.0016) N12 * −0.0045 (0.0015) N13 * 0.0083 (0.0017) C14 * −0.0002 (0.0016) C20 * −0.0100 (0.0016) C19

Rms deviation of fitted atoms = 0.0084

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0479 (3)0.1225 (3)0.7111 (2)0.0286 (6)
C20.0205 (4)0.0043 (3)0.6681 (3)0.0322 (7)
H20.09180.01690.58520.040*
C30.1071 (4)0.1217 (3)0.7369 (3)0.0332 (7)
H30.12180.21010.70060.041*
C40.2097 (4)0.1071 (3)0.8565 (3)0.0321 (7)
H40.29670.18560.90470.040*
C50.2814 (3)0.0459 (3)1.0338 (2)0.0297 (7)
H50.36870.03021.08660.037*
C60.2490 (3)0.1741 (3)1.0795 (3)0.0308 (7)
H60.31350.18681.16410.039*
C70.1201 (3)0.2888 (3)1.0020 (3)0.0284 (6)
H70.09900.37831.03460.036*
C80.0267 (3)0.2715 (3)0.8813 (2)0.0246 (6)
C90.0543 (3)0.1387 (3)0.8308 (2)0.0241 (6)
C100.1860 (3)0.0252 (3)0.9083 (2)0.0250 (6)
C110.0848 (3)0.4906 (3)0.6929 (2)0.0244 (6)
O110.0568 (2)0.4998 (2)0.66626 (17)0.0328 (5)
N120.1089 (3)0.3856 (2)0.8032 (2)0.0260 (5)
N130.2572 (3)0.3698 (3)0.8476 (2)0.0271 (5)
C140.3896 (3)0.4617 (3)0.7789 (3)0.0274 (6)
C150.5348 (4)0.6712 (3)0.5811 (3)0.0305 (7)
H150.63970.66320.60800.038*
C160.5257 (4)0.7752 (3)0.4668 (3)0.0362 (7)
H160.62420.83950.41550.045*
C170.3738 (4)0.7877 (3)0.4249 (3)0.0340 (7)
H170.36910.86020.34560.042*
C180.2305 (3)0.6949 (3)0.4986 (3)0.0303 (7)
H180.12700.70280.47000.038*
C190.2375 (3)0.5898 (3)0.6150 (2)0.0250 (6)
C200.3890 (3)0.5760 (3)0.6590 (2)0.0243 (6)
C210.5456 (3)0.4438 (4)0.8337 (3)0.0365 (7)
H210.64960.42000.76770.046*
H220.52540.35530.91130.046*
H230.56350.54460.85810.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0233 (13)0.0311 (14)0.0306 (13)0.0005 (10)0.0056 (10)0.0070 (10)
C20.0346 (17)0.0367 (18)0.0256 (15)0.0003 (14)0.0070 (13)0.0081 (13)
C30.0332 (17)0.0264 (16)0.0437 (18)0.0003 (13)0.0151 (14)0.0089 (13)
C40.0250 (16)0.0249 (16)0.0451 (18)0.0040 (12)0.0105 (13)0.0025 (13)
C50.0204 (15)0.0282 (16)0.0339 (16)0.0064 (12)0.0016 (12)0.0016 (12)
C60.0253 (16)0.0338 (17)0.0296 (15)0.0005 (13)0.0031 (12)0.0043 (12)
C70.0222 (15)0.0278 (16)0.0342 (15)0.0008 (12)0.0054 (12)0.0070 (12)
C80.0168 (14)0.0243 (15)0.0297 (15)0.0034 (11)0.0049 (11)0.0005 (11)
C90.0200 (14)0.0218 (15)0.0280 (15)0.0000 (11)0.0066 (12)0.0002 (11)
C100.0189 (14)0.0229 (15)0.0303 (15)0.0003 (11)0.0061 (11)0.0001 (11)
C110.0213 (15)0.0227 (15)0.0288 (15)0.0003 (11)0.0050 (12)0.0069 (11)
O110.0210 (11)0.0344 (12)0.0420 (12)0.0035 (8)0.0104 (9)0.0027 (9)
N120.0174 (12)0.0234 (13)0.0360 (13)0.0042 (10)0.0068 (10)0.0030 (10)
N130.0192 (13)0.0318 (14)0.0314 (13)0.0005 (10)0.0072 (10)0.0083 (10)
C140.0177 (15)0.0307 (16)0.0340 (15)0.0013 (12)0.0043 (12)0.0102 (12)
C150.0232 (15)0.0311 (17)0.0356 (16)0.0059 (12)0.0025 (12)0.0091 (13)
C160.0274 (17)0.0305 (17)0.0423 (17)0.0076 (13)0.0031 (13)0.0042 (13)
C170.0322 (17)0.0311 (17)0.0323 (16)0.0020 (13)0.0012 (13)0.0023 (12)
C180.0244 (16)0.0273 (16)0.0365 (16)0.0005 (12)0.0051 (12)0.0052 (12)
C190.0211 (15)0.0191 (14)0.0333 (15)0.0003 (11)0.0037 (12)0.0072 (11)
C200.0223 (15)0.0237 (15)0.0281 (14)0.0014 (11)0.0039 (12)0.0111 (11)
C210.0255 (16)0.049 (2)0.0359 (17)0.0034 (14)0.0089 (13)0.0098 (14)
Geometric parameters (Å, º) top
N1—C21.318 (3)C11—N121.377 (3)
N1—C91.365 (3)C11—C191.467 (3)
C2—C31.402 (4)N12—N131.381 (3)
C2—H20.95N13—C141.301 (3)
C3—C41.361 (4)C14—C201.442 (4)
C3—H30.95C14—C211.503 (3)
C4—C101.409 (4)C15—C161.372 (4)
C4—H40.95C15—C201.412 (4)
C5—C61.359 (4)C15—H150.95
C5—C101.413 (4)C16—C171.393 (4)
C5—H50.95C16—H160.95
C6—C71.414 (3)C17—C181.377 (4)
C6—H60.95C17—H170.95
C7—C81.356 (4)C18—C191.389 (4)
C7—H70.95C18—H180.95
C8—C91.413 (3)C19—C201.403 (3)
C8—N121.446 (3)C21—H210.98
C9—C101.422 (3)C21—H220.98
C11—O111.231 (3)C21—H230.98
C2—N1—C9117.4 (2)C11—N12—N13126.7 (2)
N1—C2—C3124.2 (3)C11—N12—C8119.7 (2)
N1—C2—H2117.9N13—N12—C8113.46 (19)
C3—C2—H2117.9C14—N13—N12117.6 (2)
C4—C3—C2119.0 (2)N13—C14—C20123.3 (2)
C4—C3—H3120.5N13—C14—C21115.5 (2)
C2—C3—H3120.5C20—C14—C21121.2 (2)
C3—C4—C10119.5 (3)C16—C15—C20120.3 (3)
C3—C4—H4120.2C16—C15—H15119.9
C10—C4—H4120.2C20—C15—H15119.9
C6—C5—C10120.3 (2)C15—C16—C17120.8 (3)
C6—C5—H5119.8C15—C16—H16119.6
C10—C5—H5119.8C17—C16—H16119.6
C5—C6—C7120.6 (3)C18—C17—C16120.0 (3)
C5—C6—H6119.7C18—C17—H17120.0
C7—C6—H6119.7C16—C17—H17120.0
C8—C7—C6120.2 (2)C17—C18—C19119.8 (3)
C8—C7—H7119.9C17—C18—H18120.1
C6—C7—H7119.9C19—C18—H18120.1
C7—C8—C9121.1 (2)C18—C19—C20121.0 (2)
C7—C8—N12120.5 (2)C18—C19—C11119.7 (2)
C9—C8—N12118.4 (2)C20—C19—C11119.3 (2)
N1—C9—C8119.1 (2)C19—C20—C15118.1 (2)
N1—C9—C10122.5 (2)C19—C20—C14118.4 (2)
C8—C9—C10118.4 (2)C15—C20—C14123.5 (2)
C4—C10—C5123.2 (2)C14—C21—H21109.5
C4—C10—C9117.4 (2)C14—C21—H22109.5
C5—C10—C9119.3 (2)H21—C21—H22109.5
O11—C11—N12121.0 (2)C14—C21—H23109.5
O11—C11—C19124.2 (2)H21—C21—H23109.5
N12—C11—C19114.7 (2)H22—C21—H23109.5
C9—N1—C2—C30.6 (4)C9—C8—N12—C1172.3 (3)
N1—C2—C3—C40.7 (4)C7—C8—N12—N1372.8 (3)
C2—C3—C4—C100.2 (4)C9—C8—N12—N13104.7 (2)
C10—C5—C6—C70.3 (4)C11—N12—N13—C140.6 (3)
C5—C6—C7—C80.3 (4)C8—N12—N13—C14176.2 (2)
C6—C7—C8—C90.6 (4)N12—N13—C14—C200.9 (4)
C6—C7—C8—N12178.1 (2)N12—N13—C14—C21178.0 (2)
C2—N1—C9—C8178.9 (2)C20—C15—C16—C170.6 (4)
C2—N1—C9—C100.0 (4)C15—C16—C17—C180.0 (4)
C7—C8—C9—N1177.3 (2)C16—C17—C18—C190.4 (4)
N12—C8—C9—N10.3 (3)C17—C18—C19—C200.1 (4)
C7—C8—C9—C101.6 (4)C17—C18—C19—C11179.7 (2)
N12—C8—C9—C10179.2 (2)O11—C11—C19—C184.4 (4)
C3—C4—C10—C5177.2 (2)N12—C11—C19—C18177.2 (2)
C3—C4—C10—C90.4 (4)O11—C11—C19—C20176.1 (2)
C6—C5—C10—C4178.3 (2)N12—C11—C19—C202.3 (3)
C6—C5—C10—C90.8 (4)C18—C19—C20—C150.5 (4)
N1—C9—C10—C40.5 (4)C11—C19—C20—C15179.1 (2)
C8—C9—C10—C4179.3 (2)C18—C19—C20—C14178.4 (2)
N1—C9—C10—C5177.2 (2)C11—C19—C20—C141.1 (3)
C8—C9—C10—C51.7 (3)C16—C15—C20—C190.8 (4)
O11—C11—N12—N13176.3 (2)C16—C15—C20—C14178.7 (2)
C19—C11—N12—N132.2 (3)N13—C14—C20—C190.6 (4)
O11—C11—N12—C87.1 (4)C21—C14—C20—C19178.3 (2)
C19—C11—N12—C8174.5 (2)N13—C14—C20—C15177.2 (2)
C7—C8—N12—C11110.1 (3)C21—C14—C20—C153.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O11i0.952.573.442 (3)153
C16—H16···N1ii0.952.603.469 (4)153
C21—H21···O11iii0.982.363.194 (3)142
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC18H13N3O
Mr287.31
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)7.9530 (4), 8.4914 (6), 10.8850 (7)
α, β, γ (°)77.060 (6), 74.114 (5), 86.277 (3)
V3)689.05 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.10 × 0.10 × 0.05
Data collection
DiffractometerBruker–Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.991, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
9188, 3005, 1507
Rint0.075
(sin θ/λ)max1)0.646
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.179, 0.97
No. of reflections3005
No. of parameters200
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.30

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O11i0.952.573.442 (3)153
C16—H16···N1ii0.952.603.469 (4)153
C21—H21···O11iii0.982.363.194 (3)142
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z.
 

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