Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015362/cf6200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015362/cf6200Isup2.hkl |
CCDC reference: 198328
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).
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).
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.
Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids. |
C18H13N3O | F(000) = 300 |
Mr = 287.31 | Dx = 1.385 Mg m−3 |
Triclinic, P1 | Melting point: 450-452 K K |
a = 7.9530 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4914 (6) Å | Cell parameters from 6981 reflections |
c = 10.8850 (7) Å | θ = 2.9–27.5° |
α = 77.060 (6)° | µ = 0.09 mm−1 |
β = 74.114 (5)° | T = 150 K |
γ = 86.277 (3)° | Block, colourless |
V = 689.05 (7) Å3 | 0.10 × 0.10 × 0.05 mm |
Z = 2 |
Bruker–Nonius KappaCCD area-detector diffractometer | 3005 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 1507 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.4°, θmin = 3.5° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −10→10 |
Tmin = 0.991, Tmax = 0.996 | l = −12→14 |
9188 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H-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 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C18H13N3O | γ = 86.277 (3)° |
Mr = 287.31 | V = 689.05 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9530 (4) Å | Mo Kα radiation |
b = 8.4914 (6) Å | µ = 0.09 mm−1 |
c = 10.8850 (7) Å | T = 150 K |
α = 77.060 (6)° | 0.10 × 0.10 × 0.05 mm |
β = 74.114 (5)° |
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 = 0.996 | Rint = 0.075 |
9188 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.30 e Å−3 |
3005 reflections | Δρmin = −0.30 e Å−3 |
200 parameters |
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 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.0479 (3) | 0.1225 (3) | 0.7111 (2) | 0.0286 (6) | |
C2 | 0.0205 (4) | −0.0043 (3) | 0.6681 (3) | 0.0322 (7) | |
H2 | 0.0918 | −0.0169 | 0.5852 | 0.040* | |
C3 | −0.1071 (4) | −0.1217 (3) | 0.7369 (3) | 0.0332 (7) | |
H3 | −0.1218 | −0.2101 | 0.7006 | 0.041* | |
C4 | −0.2097 (4) | −0.1071 (3) | 0.8565 (3) | 0.0321 (7) | |
H4 | −0.2967 | −0.1856 | 0.9047 | 0.040* | |
C5 | −0.2814 (3) | 0.0459 (3) | 1.0338 (2) | 0.0297 (7) | |
H5 | −0.3687 | −0.0302 | 1.0866 | 0.037* | |
C6 | −0.2490 (3) | 0.1741 (3) | 1.0795 (3) | 0.0308 (7) | |
H6 | −0.3135 | 0.1868 | 1.1641 | 0.039* | |
C7 | −0.1201 (3) | 0.2888 (3) | 1.0020 (3) | 0.0284 (6) | |
H7 | −0.0990 | 0.3783 | 1.0346 | 0.036* | |
C8 | −0.0267 (3) | 0.2715 (3) | 0.8813 (2) | 0.0246 (6) | |
C9 | −0.0543 (3) | 0.1387 (3) | 0.8308 (2) | 0.0241 (6) | |
C10 | −0.1860 (3) | 0.0252 (3) | 0.9083 (2) | 0.0250 (6) | |
C11 | 0.0848 (3) | 0.4906 (3) | 0.6929 (2) | 0.0244 (6) | |
O11 | −0.0568 (2) | 0.4998 (2) | 0.66626 (17) | 0.0328 (5) | |
N12 | 0.1089 (3) | 0.3856 (2) | 0.8032 (2) | 0.0260 (5) | |
N13 | 0.2572 (3) | 0.3698 (3) | 0.8476 (2) | 0.0271 (5) | |
C14 | 0.3896 (3) | 0.4617 (3) | 0.7789 (3) | 0.0274 (6) | |
C15 | 0.5348 (4) | 0.6712 (3) | 0.5811 (3) | 0.0305 (7) | |
H15 | 0.6397 | 0.6632 | 0.6080 | 0.038* | |
C16 | 0.5257 (4) | 0.7752 (3) | 0.4668 (3) | 0.0362 (7) | |
H16 | 0.6242 | 0.8395 | 0.4155 | 0.045* | |
C17 | 0.3738 (4) | 0.7877 (3) | 0.4249 (3) | 0.0340 (7) | |
H17 | 0.3691 | 0.8602 | 0.3456 | 0.042* | |
C18 | 0.2305 (3) | 0.6949 (3) | 0.4986 (3) | 0.0303 (7) | |
H18 | 0.1270 | 0.7028 | 0.4700 | 0.038* | |
C19 | 0.2375 (3) | 0.5898 (3) | 0.6150 (2) | 0.0250 (6) | |
C20 | 0.3890 (3) | 0.5760 (3) | 0.6590 (2) | 0.0243 (6) | |
C21 | 0.5456 (3) | 0.4438 (4) | 0.8337 (3) | 0.0365 (7) | |
H21 | 0.6496 | 0.4200 | 0.7677 | 0.046* | |
H22 | 0.5254 | 0.3553 | 0.9113 | 0.046* | |
H23 | 0.5635 | 0.5446 | 0.8581 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0233 (13) | 0.0311 (14) | 0.0306 (13) | 0.0005 (10) | −0.0056 (10) | −0.0070 (10) |
C2 | 0.0346 (17) | 0.0367 (18) | 0.0256 (15) | −0.0003 (14) | −0.0070 (13) | −0.0081 (13) |
C3 | 0.0332 (17) | 0.0264 (16) | 0.0437 (18) | −0.0003 (13) | −0.0151 (14) | −0.0089 (13) |
C4 | 0.0250 (16) | 0.0249 (16) | 0.0451 (18) | −0.0040 (12) | −0.0105 (13) | −0.0025 (13) |
C5 | 0.0204 (15) | 0.0282 (16) | 0.0339 (16) | −0.0064 (12) | −0.0016 (12) | 0.0016 (12) |
C6 | 0.0253 (16) | 0.0338 (17) | 0.0296 (15) | 0.0005 (13) | −0.0031 (12) | −0.0043 (12) |
C7 | 0.0222 (15) | 0.0278 (16) | 0.0342 (15) | −0.0008 (12) | −0.0054 (12) | −0.0070 (12) |
C8 | 0.0168 (14) | 0.0243 (15) | 0.0297 (15) | −0.0034 (11) | −0.0049 (11) | −0.0005 (11) |
C9 | 0.0200 (14) | 0.0218 (15) | 0.0280 (15) | 0.0000 (11) | −0.0066 (12) | −0.0002 (11) |
C10 | 0.0189 (14) | 0.0229 (15) | 0.0303 (15) | −0.0003 (11) | −0.0061 (11) | −0.0001 (11) |
C11 | 0.0213 (15) | 0.0227 (15) | 0.0288 (15) | −0.0003 (11) | −0.0050 (12) | −0.0069 (11) |
O11 | 0.0210 (11) | 0.0344 (12) | 0.0420 (12) | −0.0035 (8) | −0.0104 (9) | −0.0027 (9) |
N12 | 0.0174 (12) | 0.0234 (13) | 0.0360 (13) | −0.0042 (10) | −0.0068 (10) | −0.0030 (10) |
N13 | 0.0192 (13) | 0.0318 (14) | 0.0314 (13) | −0.0005 (10) | −0.0072 (10) | −0.0083 (10) |
C14 | 0.0177 (15) | 0.0307 (16) | 0.0340 (15) | −0.0013 (12) | −0.0043 (12) | −0.0102 (12) |
C15 | 0.0232 (15) | 0.0311 (17) | 0.0356 (16) | −0.0059 (12) | −0.0025 (12) | −0.0091 (13) |
C16 | 0.0274 (17) | 0.0305 (17) | 0.0423 (17) | −0.0076 (13) | 0.0031 (13) | −0.0042 (13) |
C17 | 0.0322 (17) | 0.0311 (17) | 0.0323 (16) | −0.0020 (13) | −0.0012 (13) | −0.0023 (12) |
C18 | 0.0244 (16) | 0.0273 (16) | 0.0365 (16) | −0.0005 (12) | −0.0051 (12) | −0.0052 (12) |
C19 | 0.0211 (15) | 0.0191 (14) | 0.0333 (15) | −0.0003 (11) | −0.0037 (12) | −0.0072 (11) |
C20 | 0.0223 (15) | 0.0237 (15) | 0.0281 (14) | −0.0014 (11) | −0.0039 (12) | −0.0111 (11) |
C21 | 0.0255 (16) | 0.049 (2) | 0.0359 (17) | −0.0034 (14) | −0.0089 (13) | −0.0098 (14) |
N1—C2 | 1.318 (3) | C11—N12 | 1.377 (3) |
N1—C9 | 1.365 (3) | C11—C19 | 1.467 (3) |
C2—C3 | 1.402 (4) | N12—N13 | 1.381 (3) |
C2—H2 | 0.95 | N13—C14 | 1.301 (3) |
C3—C4 | 1.361 (4) | C14—C20 | 1.442 (4) |
C3—H3 | 0.95 | C14—C21 | 1.503 (3) |
C4—C10 | 1.409 (4) | C15—C16 | 1.372 (4) |
C4—H4 | 0.95 | C15—C20 | 1.412 (4) |
C5—C6 | 1.359 (4) | C15—H15 | 0.95 |
C5—C10 | 1.413 (4) | C16—C17 | 1.393 (4) |
C5—H5 | 0.95 | C16—H16 | 0.95 |
C6—C7 | 1.414 (3) | C17—C18 | 1.377 (4) |
C6—H6 | 0.95 | C17—H17 | 0.95 |
C7—C8 | 1.356 (4) | C18—C19 | 1.389 (4) |
C7—H7 | 0.95 | C18—H18 | 0.95 |
C8—C9 | 1.413 (3) | C19—C20 | 1.403 (3) |
C8—N12 | 1.446 (3) | C21—H21 | 0.98 |
C9—C10 | 1.422 (3) | C21—H22 | 0.98 |
C11—O11 | 1.231 (3) | C21—H23 | 0.98 |
C2—N1—C9 | 117.4 (2) | C11—N12—N13 | 126.7 (2) |
N1—C2—C3 | 124.2 (3) | C11—N12—C8 | 119.7 (2) |
N1—C2—H2 | 117.9 | N13—N12—C8 | 113.46 (19) |
C3—C2—H2 | 117.9 | C14—N13—N12 | 117.6 (2) |
C4—C3—C2 | 119.0 (2) | N13—C14—C20 | 123.3 (2) |
C4—C3—H3 | 120.5 | N13—C14—C21 | 115.5 (2) |
C2—C3—H3 | 120.5 | C20—C14—C21 | 121.2 (2) |
C3—C4—C10 | 119.5 (3) | C16—C15—C20 | 120.3 (3) |
C3—C4—H4 | 120.2 | C16—C15—H15 | 119.9 |
C10—C4—H4 | 120.2 | C20—C15—H15 | 119.9 |
C6—C5—C10 | 120.3 (2) | C15—C16—C17 | 120.8 (3) |
C6—C5—H5 | 119.8 | C15—C16—H16 | 119.6 |
C10—C5—H5 | 119.8 | C17—C16—H16 | 119.6 |
C5—C6—C7 | 120.6 (3) | C18—C17—C16 | 120.0 (3) |
C5—C6—H6 | 119.7 | C18—C17—H17 | 120.0 |
C7—C6—H6 | 119.7 | C16—C17—H17 | 120.0 |
C8—C7—C6 | 120.2 (2) | C17—C18—C19 | 119.8 (3) |
C8—C7—H7 | 119.9 | C17—C18—H18 | 120.1 |
C6—C7—H7 | 119.9 | C19—C18—H18 | 120.1 |
C7—C8—C9 | 121.1 (2) | C18—C19—C20 | 121.0 (2) |
C7—C8—N12 | 120.5 (2) | C18—C19—C11 | 119.7 (2) |
C9—C8—N12 | 118.4 (2) | C20—C19—C11 | 119.3 (2) |
N1—C9—C8 | 119.1 (2) | C19—C20—C15 | 118.1 (2) |
N1—C9—C10 | 122.5 (2) | C19—C20—C14 | 118.4 (2) |
C8—C9—C10 | 118.4 (2) | C15—C20—C14 | 123.5 (2) |
C4—C10—C5 | 123.2 (2) | C14—C21—H21 | 109.5 |
C4—C10—C9 | 117.4 (2) | C14—C21—H22 | 109.5 |
C5—C10—C9 | 119.3 (2) | H21—C21—H22 | 109.5 |
O11—C11—N12 | 121.0 (2) | C14—C21—H23 | 109.5 |
O11—C11—C19 | 124.2 (2) | H21—C21—H23 | 109.5 |
N12—C11—C19 | 114.7 (2) | H22—C21—H23 | 109.5 |
C9—N1—C2—C3 | 0.6 (4) | C9—C8—N12—C11 | 72.3 (3) |
N1—C2—C3—C4 | −0.7 (4) | C7—C8—N12—N13 | 72.8 (3) |
C2—C3—C4—C10 | 0.2 (4) | C9—C8—N12—N13 | −104.7 (2) |
C10—C5—C6—C7 | 0.3 (4) | C11—N12—N13—C14 | −0.6 (3) |
C5—C6—C7—C8 | −0.3 (4) | C8—N12—N13—C14 | 176.2 (2) |
C6—C7—C8—C9 | −0.6 (4) | N12—N13—C14—C20 | −0.9 (4) |
C6—C7—C8—N12 | −178.1 (2) | N12—N13—C14—C21 | 178.0 (2) |
C2—N1—C9—C8 | 178.9 (2) | C20—C15—C16—C17 | −0.6 (4) |
C2—N1—C9—C10 | 0.0 (4) | C15—C16—C17—C18 | 0.0 (4) |
C7—C8—C9—N1 | −177.3 (2) | C16—C17—C18—C19 | 0.4 (4) |
N12—C8—C9—N1 | 0.3 (3) | C17—C18—C19—C20 | −0.1 (4) |
C7—C8—C9—C10 | 1.6 (4) | C17—C18—C19—C11 | −179.7 (2) |
N12—C8—C9—C10 | 179.2 (2) | O11—C11—C19—C18 | −4.4 (4) |
C3—C4—C10—C5 | −177.2 (2) | N12—C11—C19—C18 | 177.2 (2) |
C3—C4—C10—C9 | 0.4 (4) | O11—C11—C19—C20 | 176.1 (2) |
C6—C5—C10—C4 | 178.3 (2) | N12—C11—C19—C20 | −2.3 (3) |
C6—C5—C10—C9 | 0.8 (4) | C18—C19—C20—C15 | −0.5 (4) |
N1—C9—C10—C4 | −0.5 (4) | C11—C19—C20—C15 | 179.1 (2) |
C8—C9—C10—C4 | −179.3 (2) | C18—C19—C20—C14 | −178.4 (2) |
N1—C9—C10—C5 | 177.2 (2) | C11—C19—C20—C14 | 1.1 (3) |
C8—C9—C10—C5 | −1.7 (3) | C16—C15—C20—C19 | 0.8 (4) |
O11—C11—N12—N13 | −176.3 (2) | C16—C15—C20—C14 | 178.7 (2) |
C19—C11—N12—N13 | 2.2 (3) | N13—C14—C20—C19 | 0.6 (4) |
O11—C11—N12—C8 | 7.1 (4) | C21—C14—C20—C19 | −178.3 (2) |
C19—C11—N12—C8 | −174.5 (2) | N13—C14—C20—C15 | −177.2 (2) |
C7—C8—N12—C11 | −110.1 (3) | C21—C14—C20—C15 | 3.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O11i | 0.95 | 2.57 | 3.442 (3) | 153 |
C16—H16···N1ii | 0.95 | 2.60 | 3.469 (4) | 153 |
C21—H21···O11iii | 0.98 | 2.36 | 3.194 (3) | 142 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H13N3O |
Mr | 287.31 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 689.05 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.10 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Bruker–Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.991, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9188, 3005, 1507 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.646 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.179, 0.97 |
No. of reflections | 3005 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O11i | 0.95 | 2.57 | 3.442 (3) | 153 |
C16—H16···N1ii | 0.95 | 2.60 | 3.469 (4) | 153 |
C21—H21···O11iii | 0.98 | 2.36 | 3.194 (3) | 142 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z. |
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.