Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005348/na6207sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005348/na6207Isup2.hkl |
CCDC reference: 209959
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.107
- Data-to-parameter ratio = 15.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Quinoline-4-carboxaldehyde (1.0 mmol) was dissolved in hot absolute ethanol (10 ml) and an equimolar amount of N-(4-bromo-2-nitrophenyl)-N-methylhydrazine dissolved in hot absolute ethanol (10 ml) was added. The mixture was refluxed on a steam bath for 3 h. The crude product which precipitated on cooling was recrytallized from ethanol. Yield 97%, m.p.:464–465 K; IR (KBr): ν 3090–3010, 3000–2930, 1585, 1495 and 1375, 1100, 750 cm−1; 1H NMR (DMSO-d6, δ, 200 MHz): 3.66 (s, N—CH3, 3H), 7.53–8.91 (m, ArH and CH, 10H); MS: m/z 385 (M+), 155 (M − 230), 128 (M − 257), 101 (M − 284); UV (CHCl3): λmax 248.1, 351.3 nm; elemental analysis, C17H13BrN4O2 requires/found: C 52.99/52.63, H 3.40/3.43, N 14.54/14.41%.
All H atoms were located geometrically and constrained to ride on their parent atoms. [Please provide a correct description of the H-atom treatment; some atoms appear to have been refined]
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens,1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. An ORTEP-3 (Farrugia, 1997) drawing of the title compound, showing the labelling of the non-H atoms. Displacement ellipsoids are shown at the 50% probability level. |
C17H13BrN4O2 | F(000) = 776 |
Mr = 385.22 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.7415 (11) Å | Cell parameters from 9640 reflections |
b = 6.9924 (6) Å | θ = 2.6–28.3° |
c = 17.9671 (15) Å | µ = 2.62 mm−1 |
β = 98.641 (2)° | T = 293 K |
V = 1582.6 (2) Å3 | Needle, yellow |
Z = 4 | 0.44 × 0.22 × 0.10 mm |
Siemens SMART CCD area-detector diffractometer | 3858 independent reflections |
Radiation source: fine-focus sealed tube | 1982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.6° |
ω scans | h = −16→16 |
Absorption correction: empirical (using intensity measurements) (SADABS, Sheldrick, 1996) | k = −9→9 |
Tmin = 0.506, Tmax = 0.770 | l = −23→16 |
9585 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0291P)2 + 1.2305P] where P = (Fo2 + 2Fc2)/3 |
3858 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.58 e Å−3 |
C17H13BrN4O2 | V = 1582.6 (2) Å3 |
Mr = 385.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.7415 (11) Å | µ = 2.62 mm−1 |
b = 6.9924 (6) Å | T = 293 K |
c = 17.9671 (15) Å | 0.44 × 0.22 × 0.10 mm |
β = 98.641 (2)° |
Siemens SMART CCD area-detector diffractometer | 3858 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS, Sheldrick, 1996) | 1982 reflections with I > 2σ(I) |
Tmin = 0.506, Tmax = 0.770 | Rint = 0.041 |
9585 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.42 e Å−3 |
3858 reflections | Δρmin = −0.58 e Å−3 |
245 parameters |
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 | ||
Br1 | 0.64193 (3) | 0.65227 (7) | 0.01310 (2) | 0.06777 (19) | |
O1 | 1.0607 (2) | 0.6788 (5) | −0.04704 (16) | 0.0793 (10) | |
O2 | 1.0303 (2) | 0.9715 (4) | −0.08065 (14) | 0.0597 (8) | |
N1 | 1.4116 (2) | 0.7395 (5) | −0.20382 (19) | 0.0576 (9) | |
N2 | 1.0138 (2) | 0.7736 (4) | −0.21982 (14) | 0.0338 (6) | |
N3 | 0.9069 (2) | 0.7931 (4) | −0.23792 (14) | 0.0355 (7) | |
N4 | 1.0033 (2) | 0.8046 (5) | −0.07582 (15) | 0.0434 (8) | |
C1 | 1.2353 (3) | 0.7932 (6) | −0.1750 (2) | 0.0469 (10) | |
C2 | 1.3460 (3) | 0.7748 (6) | −0.1561 (2) | 0.0593 (11) | |
H2A | 1.3748 | 0.7889 | −0.1057 | 0.071* | |
C3 | 1.3683 (3) | 0.7219 (5) | −0.2784 (2) | 0.0443 (9) | |
C4 | 1.4367 (3) | 0.6844 (6) | −0.3311 (3) | 0.0608 (12) | |
H4A | 1.5092 | 0.6722 | −0.3147 | 0.073* | |
C5 | 1.3993 (3) | 0.6655 (6) | −0.4054 (2) | 0.0609 (11) | |
H5A | 1.4461 | 0.6424 | −0.4394 | 0.073* | |
C6 | 1.2903 (3) | 0.6808 (6) | −0.4311 (2) | 0.0512 (10) | |
C7 | 1.2214 (3) | 0.7159 (5) | −0.38148 (19) | 0.0411 (9) | |
H7A | 1.1492 | 0.7257 | −0.3994 | 0.049* | |
C8 | 1.2569 (2) | 0.7380 (5) | −0.30326 (19) | 0.0347 (8) | |
C9 | 1.1892 (3) | 0.7737 (5) | −0.24886 (19) | 0.0372 (8) | |
C10 | 1.0737 (3) | 0.7900 (5) | −0.2705 (2) | 0.0369 (8) | |
C11 | 0.8477 (2) | 0.7619 (5) | −0.17985 (18) | 0.0308 (7) | |
C12 | 0.7378 (3) | 0.7299 (5) | −0.19441 (19) | 0.0386 (8) | |
H12A | 0.7046 | 0.7294 | −0.2442 | 0.046* | |
C13 | 0.6773 (3) | 0.6993 (5) | −0.1385 (2) | 0.0447 (9) | |
H13A | 0.6043 | 0.6834 | −0.1505 | 0.054* | |
C14 | 0.7253 (3) | 0.6923 (5) | −0.06443 (19) | 0.0404 (9) | |
C15 | 0.8330 (3) | 0.7183 (5) | −0.0464 (2) | 0.0394 (9) | |
C16 | 0.8919 (2) | 0.7561 (5) | −0.10334 (18) | 0.0334 (8) | |
C17 | 0.8576 (3) | 0.8199 (7) | −0.3160 (2) | 0.0443 (10) | |
H10 | 1.052 (3) | 0.812 (5) | −0.322 (2) | 0.054 (11)* | |
H15 | 0.869 (3) | 0.714 (5) | 0.0045 (19) | 0.052 (11)* | |
H1 | 1.195 (3) | 0.826 (5) | −0.1413 (19) | 0.049 (11)* | |
H6 | 1.261 (3) | 0.665 (6) | −0.485 (2) | 0.070 (13)* | |
H217 | 0.865 (3) | 0.703 (6) | −0.345 (2) | 0.060 (12)* | |
H117 | 0.790 (3) | 0.851 (5) | −0.3194 (19) | 0.050 (11)* | |
H317 | 0.894 (3) | 0.925 (5) | −0.340 (2) | 0.062 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0472 (2) | 0.1000 (4) | 0.0613 (3) | −0.0102 (3) | 0.02513 (19) | −0.0012 (3) |
O1 | 0.0403 (16) | 0.120 (3) | 0.072 (2) | 0.0121 (18) | −0.0099 (14) | 0.048 (2) |
O2 | 0.0471 (16) | 0.068 (2) | 0.0658 (19) | −0.0268 (15) | 0.0133 (13) | −0.0254 (16) |
N1 | 0.0310 (17) | 0.081 (3) | 0.057 (2) | −0.0049 (17) | −0.0046 (16) | 0.0004 (19) |
N2 | 0.0251 (14) | 0.0399 (17) | 0.0346 (15) | −0.0005 (12) | −0.0009 (12) | 0.0005 (13) |
N3 | 0.0253 (14) | 0.0469 (19) | 0.0322 (15) | 0.0044 (12) | −0.0023 (11) | 0.0017 (13) |
N4 | 0.0312 (16) | 0.068 (3) | 0.0306 (16) | −0.0049 (16) | 0.0049 (13) | −0.0036 (16) |
C1 | 0.034 (2) | 0.059 (3) | 0.047 (2) | −0.0087 (18) | 0.0057 (18) | −0.003 (2) |
C2 | 0.042 (2) | 0.084 (3) | 0.048 (2) | −0.012 (2) | −0.0066 (19) | 0.002 (2) |
C3 | 0.0276 (18) | 0.049 (2) | 0.055 (3) | −0.0035 (16) | 0.0033 (17) | 0.0024 (19) |
C4 | 0.0260 (19) | 0.074 (3) | 0.083 (3) | −0.0032 (19) | 0.0102 (19) | 0.001 (3) |
C5 | 0.047 (2) | 0.079 (3) | 0.062 (3) | −0.008 (2) | 0.025 (2) | −0.004 (2) |
C6 | 0.045 (2) | 0.063 (3) | 0.047 (2) | −0.005 (2) | 0.0131 (18) | 0.001 (2) |
C7 | 0.0339 (19) | 0.043 (2) | 0.047 (2) | −0.0042 (16) | 0.0070 (16) | 0.0026 (17) |
C8 | 0.0305 (18) | 0.032 (2) | 0.041 (2) | −0.0051 (15) | 0.0041 (15) | 0.0067 (16) |
C9 | 0.0325 (18) | 0.036 (2) | 0.043 (2) | −0.0049 (15) | 0.0034 (15) | 0.0044 (16) |
C10 | 0.0291 (18) | 0.043 (2) | 0.038 (2) | −0.0014 (15) | 0.0018 (16) | 0.0016 (17) |
C11 | 0.0248 (16) | 0.0308 (19) | 0.0359 (18) | 0.0041 (14) | 0.0014 (14) | −0.0040 (15) |
C12 | 0.0289 (18) | 0.044 (2) | 0.040 (2) | −0.0004 (15) | −0.0044 (15) | −0.0047 (17) |
C13 | 0.0253 (17) | 0.050 (3) | 0.059 (3) | −0.0032 (16) | 0.0059 (16) | −0.0089 (19) |
C14 | 0.0296 (18) | 0.046 (2) | 0.048 (2) | −0.0008 (16) | 0.0112 (16) | −0.0041 (18) |
C15 | 0.036 (2) | 0.044 (2) | 0.037 (2) | 0.0004 (16) | 0.0021 (16) | 0.0004 (18) |
C16 | 0.0228 (16) | 0.038 (2) | 0.0374 (19) | −0.0011 (14) | −0.0009 (14) | −0.0014 (16) |
C17 | 0.035 (2) | 0.061 (3) | 0.034 (2) | 0.008 (2) | −0.0030 (16) | 0.001 (2) |
Br1—C14 | 1.895 (3) | C6—C7 | 1.364 (5) |
O1—N4 | 1.209 (4) | C6—H6 | 0.98 (4) |
O2—N4 | 1.224 (4) | C7—C8 | 1.418 (5) |
N1—C2 | 1.308 (5) | C7—H7A | 0.9300 |
N1—C3 | 1.375 (4) | C8—C9 | 1.419 (4) |
N2—C10 | 1.278 (4) | C9—C10 | 1.469 (4) |
N2—N3 | 1.359 (3) | C10—H10 | 0.94 (3) |
N3—C11 | 1.393 (4) | C11—C12 | 1.403 (4) |
N3—C17 | 1.460 (4) | C11—C16 | 1.405 (4) |
N4—C16 | 1.471 (4) | C12—C13 | 1.371 (5) |
C1—C9 | 1.374 (5) | C12—H12A | 0.9300 |
C1—C2 | 1.407 (5) | C13—C14 | 1.380 (5) |
C1—H1 | 0.88 (3) | C13—H13A | 0.9300 |
C2—H2A | 0.9300 | C14—C15 | 1.373 (5) |
C3—C4 | 1.405 (5) | C15—C16 | 1.382 (4) |
C3—C8 | 1.427 (4) | C15—H15 | 0.96 (3) |
C4—C5 | 1.355 (5) | C17—H217 | 0.98 (4) |
C4—H4A | 0.9300 | C17—H117 | 0.88 (4) |
C5—C6 | 1.401 (5) | C17—H317 | 1.00 (4) |
C5—H5A | 0.9300 | ||
C2—N1—C3 | 116.9 (3) | C9—C8—C3 | 118.5 (3) |
C10—N2—N3 | 120.3 (3) | C1—C9—C8 | 117.8 (3) |
N2—N3—C11 | 116.2 (2) | C1—C9—C10 | 120.9 (3) |
N2—N3—C17 | 120.9 (3) | C8—C9—C10 | 121.3 (3) |
C11—N3—C17 | 122.5 (3) | N2—C10—C9 | 119.1 (3) |
O1—N4—O2 | 124.5 (3) | N2—C10—H10 | 127 (2) |
O1—N4—C16 | 117.9 (3) | C9—C10—H10 | 114 (2) |
O2—N4—C16 | 117.6 (3) | N3—C11—C12 | 121.5 (3) |
C9—C1—C2 | 119.5 (4) | N3—C11—C16 | 123.7 (3) |
C9—C1—H1 | 119 (2) | C12—C11—C16 | 114.8 (3) |
C2—C1—H1 | 121 (2) | C13—C12—C11 | 122.9 (3) |
N1—C2—C1 | 125.1 (4) | C13—C12—H12A | 118.5 |
N1—C2—H2A | 117.5 | C11—C12—H12A | 118.5 |
C1—C2—H2A | 117.5 | C12—C13—C14 | 119.7 (3) |
N1—C3—C4 | 118.3 (3) | C12—C13—H13A | 120.2 |
N1—C3—C8 | 122.2 (3) | C14—C13—H13A | 120.2 |
C4—C3—C8 | 119.5 (3) | C15—C14—C13 | 120.3 (3) |
C5—C4—C3 | 121.4 (3) | C15—C14—Br1 | 119.8 (3) |
C5—C4—H4A | 119.3 | C13—C14—Br1 | 119.9 (2) |
C3—C4—H4A | 119.3 | C14—C15—C16 | 119.0 (3) |
C4—C5—C6 | 120.1 (4) | C14—C15—H15 | 122 (2) |
C4—C5—H5A | 119.9 | C16—C15—H15 | 119 (2) |
C6—C5—H5A | 119.9 | C15—C16—C11 | 123.2 (3) |
C7—C6—C5 | 120.1 (4) | C15—C16—N4 | 113.5 (3) |
C7—C6—H6 | 118 (2) | C11—C16—N4 | 123.1 (3) |
C5—C6—H6 | 121 (2) | N3—C17—H217 | 110 (2) |
C6—C7—C8 | 121.8 (3) | N3—C17—H117 | 112 (2) |
C6—C7—H7A | 119.1 | H217—C17—H117 | 110 (3) |
C8—C7—H7A | 119.1 | N3—C17—H317 | 111 (2) |
C7—C8—C9 | 124.4 (3) | H217—C17—H317 | 107 (3) |
C7—C8—C3 | 117.1 (3) | H117—C17—H317 | 107 (3) |
C10—N2—N3—C11 | 176.4 (3) | C1—C9—C10—N2 | −17.7 (5) |
C10—N2—N3—C17 | 4.3 (5) | C8—C9—C10—N2 | 162.4 (3) |
C3—N1—C2—C1 | 1.0 (7) | N2—N3—C11—C12 | −163.7 (3) |
C9—C1—C2—N1 | −0.1 (7) | C17—N3—C11—C12 | 8.3 (5) |
C2—N1—C3—C4 | 179.9 (4) | N2—N3—C11—C16 | 15.1 (5) |
C2—N1—C3—C8 | −1.0 (6) | C17—N3—C11—C16 | −172.9 (4) |
N1—C3—C4—C5 | −180.0 (4) | N3—C11—C12—C13 | −179.8 (3) |
C8—C3—C4—C5 | 0.9 (6) | C16—C11—C12—C13 | 1.3 (5) |
C3—C4—C5—C6 | −0.9 (7) | C11—C12—C13—C14 | −2.4 (6) |
C4—C5—C6—C7 | 0.4 (6) | C12—C13—C14—C15 | 0.9 (5) |
C5—C6—C7—C8 | 0.0 (6) | C12—C13—C14—Br1 | 179.5 (3) |
C6—C7—C8—C9 | −179.6 (4) | C13—C14—C15—C16 | 1.5 (5) |
C6—C7—C8—C3 | 0.0 (5) | Br1—C14—C15—C16 | −177.1 (3) |
N1—C3—C8—C7 | −179.6 (3) | C14—C15—C16—C11 | −2.6 (5) |
C4—C3—C8—C7 | −0.4 (5) | C14—C15—C16—N4 | 172.8 (3) |
N1—C3—C8—C9 | 0.1 (5) | N3—C11—C16—C15 | −177.6 (3) |
C4—C3—C8—C9 | 179.3 (3) | C12—C11—C16—C15 | 1.2 (5) |
C2—C1—C9—C8 | −0.8 (6) | N3—C11—C16—N4 | 7.4 (5) |
C2—C1—C9—C10 | 179.3 (4) | C12—C11—C16—N4 | −173.8 (3) |
C7—C8—C9—C1 | −179.5 (3) | O1—N4—C16—C15 | 69.7 (4) |
C3—C8—C9—C1 | 0.8 (5) | O2—N4—C16—C15 | −107.1 (4) |
C7—C8—C9—C10 | 0.3 (5) | O1—N4—C16—C11 | −114.9 (4) |
C3—C8—C9—C10 | −179.4 (3) | O2—N4—C16—C11 | 68.3 (4) |
N3—N2—C10—C9 | 178.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N1i | 0.93 | 2.53 | 3.424 (5) | 162 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H13BrN4O2 |
Mr | 385.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.7415 (11), 6.9924 (6), 17.9671 (15) |
β (°) | 98.641 (2) |
V (Å3) | 1582.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.62 |
Crystal size (mm) | 0.44 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS, Sheldrick, 1996) |
Tmin, Tmax | 0.506, 0.770 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9585, 3858, 1982 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.107, 1.04 |
No. of reflections | 3858 |
No. of parameters | 245 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.58 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens,1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Br1—C14 | 1.895 (3) | N2—C10 | 1.278 (4) |
O1—N4 | 1.209 (4) | N2—N3 | 1.359 (3) |
O2—N4 | 1.224 (4) | N3—C11 | 1.393 (4) |
N1—C2 | 1.308 (5) | N3—C17 | 1.460 (4) |
N1—C3 | 1.375 (4) | N4—C16 | 1.471 (4) |
C2—N1—C3 | 116.9 (3) | N1—C3—C8 | 122.2 (3) |
C10—N2—N3 | 120.3 (3) | C7—C8—C9 | 124.4 (3) |
N2—N3—C11 | 116.2 (2) | N2—C10—C9 | 119.1 (3) |
N2—N3—C17 | 120.9 (3) | N3—C11—C12 | 121.5 (3) |
C11—N3—C17 | 122.5 (3) | N3—C11—C16 | 123.7 (3) |
O1—N4—O2 | 124.5 (3) | C15—C14—Br1 | 119.8 (3) |
O1—N4—C16 | 117.9 (3) | C13—C14—Br1 | 119.9 (2) |
O2—N4—C16 | 117.6 (3) | C15—C16—N4 | 113.5 (3) |
N1—C2—C1 | 125.1 (4) | C11—C16—N4 | 123.1 (3) |
N1—C3—C4 | 118.3 (3) | ||
C10—N2—N3—C11 | 176.4 (3) | C12—C13—C14—Br1 | 179.5 (3) |
C10—N2—N3—C17 | 4.3 (5) | Br1—C14—C15—C16 | −177.1 (3) |
N3—N2—C10—C9 | 178.2 (3) | C14—C15—C16—N4 | 172.8 (3) |
C1—C9—C10—N2 | −17.7 (5) | N3—C11—C16—C15 | −177.6 (3) |
C8—C9—C10—N2 | 162.4 (3) | N3—C11—C16—N4 | 7.4 (5) |
N2—N3—C11—C12 | −163.7 (3) | C12—C11—C16—N4 | −173.8 (3) |
C17—N3—C11—C12 | 8.3 (5) | O1—N4—C16—C15 | 69.7 (4) |
N2—N3—C11—C16 | 15.1 (5) | O2—N4—C16—C15 | −107.1 (4) |
C17—N3—C11—C16 | −172.9 (4) | O1—N4—C16—C11 | −114.9 (4) |
N3—C11—C12—C13 | −179.8 (3) | O2—N4—C16—C11 | 68.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N1i | 0.93 | 2.53 | 3.424 (5) | 162 |
Symmetry code: (i) x−1, y, z. |
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Hydrazones are widely used both in organic syntheses and industrial works because of their reaction abilities, such as ring closure, cycloaddiation, coupling, etc. In addition, because of their biological activities, heteroaromatic hydrazones and derivatives are medicinally important compounds and they are under investigation as potential anticancer and anti-HIV reagents (Kirk-Othmer, 1980; Gürsoy et al., 1997). In view of this, the crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation.
The molecular structure of (I) is shown in Fig. 1. The C10═N2 bond length of 1.278 (4) Å is longer than typical double bonds observed in similar structures, viz. 1.265 (4) (Öztürk et al., 2001), 1.267 (3) (Akkurt et al., 2001) and 1.265 (4) Å (Özturk et al., 2001). The C16—N4 bond length [1.471 (4) Å] of the nitro group in (I) is close to the standard value for this type of bond (Allen et al., 1987). In the quinoline ring, the C7—C8—C9 angle is larger than 120° [124.4 (3)°] and the N1—C3—C4 angle is smaller than 120° [118.3 (3)°].
The C9—C10═N2—N3(C17)—C11 central chain is planar [maximum displacement of −0.037 (3) Å for atom N3] and forms dihedral angles of 18.4 (1) and 12.8 (1)° with the quinoline and phenyl planes, respectively.
There is a weak hydrogen bond calculated by PARST97 (Nardelli, 1995), given in Table 2, and the H···A = 2.53 Å distance is less than the sum of the van der Waals radii.