Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047848/hb2564sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047848/hb2564Isup2.hkl |
CCDC reference: 667307
Key indicators
- Single-crystal X-ray study
- T = 98 K
- Mean (C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.132
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.798 1.000 Tmin(prime) and Tmax expected: 0.963 0.995 RR(prime) = 0.825 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT414_ALERT_2_C Short Intra D-H..H-X H3 .. H3N .. 1.92 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.995 Tmax scaled 0.995 Tmin scaled 0.794
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Methyl anthranilate (5.0 g, 33.1 mmol) was mixed with HCl (11 ml) and water (11 ml) and digested in a water bath for 1 h. The hydrochloride was cooled to 278 K and diazotized with ice-cold aqueous NaNO2 solution (5.0 g, 72.45 mmol, 25 ml). A cold solution of quinolin-8-ol (5.0 g, 34.4 mmol), previously dissolved in methanol solution (70 ml), was then added to the cold diazonium salt solution with vigorous stirring maintaining the temperature around 273 K. A light-orange colour developed and the stirring was continued for 1 h. A saturated solution of potassium acetate was then added to neutralize the hydrochloric acid, thereupon a deep-red precipitate appeared and stirring was continued for an additional hour. The reaction mixture was kept overnight in a refrigerator followed by 2 h at room temperature. The precipitate was filtered, washed several times with water to remove soluble starting materials, and then dried in air. The crude product was washed with hexane to remove any tarry materials, dried in vacuo and recrystallization from a methanol solution afforded orange microcrystalline (I) in 53.6% (5.67 g) yield. Red crystals (m.p. 434–435 K) of (I) suitable for an X-ray crystal structure determination were obtained from the slow evaporation of an ethylacetate/methanol (v/v, 1:1) solution. Elemental analysis, found: C 66.40, H 4.23, N 13.56%; C17H13O3N3 requires C 66.44, H 4.26, N 13.67%.
All H atoms were included in the riding-model approximation, with N—H = 0.88 Å and C—H = 0.95 to 0.98 Å, and with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl-C).
The title compound, C17H13O3N3 (I) was prepared during an on-going study of the coordination chemistry of organotin(IV) 5-[(E)-2-((aryl)-1-diazenyl)quinolin-8-olates] (Basu Baul, Mizar, Lyčka et al. (2006); Basu Baul, Mizar, Song et al. (2006).
The crystal structure shows (I), (Fig. 1), to exist as the phenylhydrazone tautomer rather than in the azo form (Sawicki, 1957). The non-H atoms in (I) are effectivlely co-planar and the dihedral angle between the N1/C1—C9 and C10—C15 ring planes is 1.33 (10)°. An intramolecular N3—H···O2 hydrogen bond contributes to the stability of the observed conformation; an intramolecular C12—H···O3 interaction is also noted. Intermolecular C8—H···O1 interactions lead to the formation of supramolecular chains aligned along the b axis (Fig. 2 & Table 1). These stack side-by-side to form layers and interactions between these layers are of the type C—H···O and C—H···N and involve the methyl groups (Fig. 3).
A very closely related molecule characterized in the tautomeric form shown in the Scheme has been observed previously in a dimeric dibenzyltin structure (Basu Baul et al., 2005).
For related literature, see: Sawicki (1957); Basu Baul, Mizar, Lyčka et al. (2006); Basu Baul, Mizar, Song et al. (2006). For a related structure, see: Basu Baul et al. (2005).
Data collection: CrystalClear (Rigaku Americas Corporation, 2005); cell refinement: CrystalClear (Rigaku Americas Corporation, 2005); data reduction: CrystalClear (Rigaku Americas Corporation, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C17H13N3O3 | F(000) = 1280 |
Mr = 307.30 | Dx = 1.525 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 7939 reflections |
a = 26.695 (3) Å | θ = 2.6–29.6° |
b = 8.2513 (9) Å | µ = 0.11 mm−1 |
c = 13.5873 (16) Å | T = 98 K |
β = 116.589 (5)° | Prism, red |
V = 2676.3 (5) Å3 | 0.35 × 0.13 × 0.05 mm |
Z = 8 |
Rigaku AFC12K/SATURN724 diffractometer | 2329 independent reflections |
Radiation source: fine-focus sealed tube | 2165 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = 0→31 |
Tmin = 0.798, Tmax = 1 | k = −9→9 |
4109 measured reflections | l = −16→14 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.36 | w = 1/[σ2(Fo2) + (0.0357P)2 + 4.7653P] where P = (Fo2 + 2Fc2)/3 |
2329 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C17H13N3O3 | V = 2676.3 (5) Å3 |
Mr = 307.30 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 26.695 (3) Å | µ = 0.11 mm−1 |
b = 8.2513 (9) Å | T = 98 K |
c = 13.5873 (16) Å | 0.35 × 0.13 × 0.05 mm |
β = 116.589 (5)° |
Rigaku AFC12K/SATURN724 diffractometer | 2329 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2165 reflections with I > 2σ(I) |
Tmin = 0.798, Tmax = 1 | Rint = 0.024 |
4109 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.36 | Δρmax = 0.24 e Å−3 |
2329 reflections | Δρmin = −0.23 e Å−3 |
209 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 | ||
O1 | 0.34053 (7) | 1.3572 (2) | −0.08723 (14) | 0.0274 (4) | |
O2 | 0.61943 (7) | 1.0578 (2) | 0.29517 (13) | 0.0204 (4) | |
O3 | 0.69937 (6) | 0.9308 (2) | 0.39955 (13) | 0.0206 (4) | |
N1 | 0.30057 (8) | 1.0510 (3) | −0.15349 (16) | 0.0214 (5) | |
N2 | 0.48060 (8) | 0.8551 (3) | 0.09386 (16) | 0.0196 (5) | |
N3 | 0.53313 (8) | 0.8769 (3) | 0.16930 (16) | 0.0215 (5) | |
H3N | 0.5460 | 0.9756 | 0.1903 | 0.026* | |
C1 | 0.37145 (10) | 1.2430 (3) | −0.04737 (19) | 0.0203 (5) | |
C2 | 0.42878 (10) | 1.2680 (3) | 0.0373 (2) | 0.0252 (6) | |
H2 | 0.4414 | 1.3755 | 0.0604 | 0.030* | |
C3 | 0.46412 (10) | 1.1451 (3) | 0.0834 (2) | 0.0254 (6) | |
H3 | 0.5011 | 1.1680 | 0.1378 | 0.030* | |
C4 | 0.44828 (9) | 0.9807 (3) | 0.05351 (19) | 0.0189 (5) | |
C5 | 0.39130 (10) | 0.9464 (3) | −0.02835 (18) | 0.0187 (5) | |
C6 | 0.37130 (10) | 0.7905 (3) | −0.05822 (19) | 0.0214 (5) | |
H6 | 0.3953 | 0.7003 | −0.0262 | 0.026* | |
C7 | 0.31712 (10) | 0.7666 (3) | −0.13366 (19) | 0.0232 (6) | |
H7 | 0.3028 | 0.6601 | −0.1546 | 0.028* | |
C8 | 0.28330 (10) | 0.9001 (3) | −0.17926 (19) | 0.0232 (6) | |
H8 | 0.2456 | 0.8822 | −0.2320 | 0.028* | |
C9 | 0.35390 (10) | 1.0730 (3) | −0.07851 (19) | 0.0198 (5) | |
C10 | 0.56749 (10) | 0.7457 (3) | 0.21470 (19) | 0.0203 (5) | |
C11 | 0.62287 (10) | 0.7696 (3) | 0.29446 (19) | 0.0191 (5) | |
C12 | 0.65655 (10) | 0.6352 (3) | 0.3393 (2) | 0.0220 (6) | |
H12 | 0.6940 | 0.6503 | 0.3941 | 0.026* | |
C13 | 0.63740 (11) | 0.4825 (3) | 0.3067 (2) | 0.0273 (6) | |
H13 | 0.6611 | 0.3919 | 0.3387 | 0.033* | |
C14 | 0.58308 (11) | 0.4604 (3) | 0.2267 (2) | 0.0317 (6) | |
H14 | 0.5697 | 0.3539 | 0.2025 | 0.038* | |
C15 | 0.54847 (10) | 0.5896 (3) | 0.1819 (2) | 0.0277 (6) | |
H15 | 0.5110 | 0.5723 | 0.1279 | 0.033* | |
C16 | 0.64564 (10) | 0.9334 (3) | 0.32801 (19) | 0.0180 (5) | |
C17 | 0.72608 (10) | 1.0850 (3) | 0.4336 (2) | 0.0230 (5) | |
H17A | 0.7156 | 1.1550 | 0.3691 | 0.034* | |
H17B | 0.7668 | 1.0704 | 0.4703 | 0.034* | |
H17C | 0.7141 | 1.1354 | 0.4849 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0231 (9) | 0.0265 (10) | 0.0283 (10) | 0.0061 (8) | 0.0075 (8) | 0.0022 (8) |
O2 | 0.0177 (8) | 0.0177 (9) | 0.0228 (9) | 0.0024 (7) | 0.0066 (7) | 0.0004 (7) |
O3 | 0.0147 (8) | 0.0211 (9) | 0.0202 (8) | −0.0003 (7) | 0.0026 (7) | −0.0005 (7) |
N1 | 0.0138 (10) | 0.0327 (12) | 0.0159 (10) | 0.0013 (9) | 0.0050 (8) | −0.0004 (9) |
N2 | 0.0147 (10) | 0.0246 (11) | 0.0180 (10) | −0.0007 (9) | 0.0062 (8) | −0.0007 (9) |
N3 | 0.0143 (10) | 0.0199 (11) | 0.0247 (11) | −0.0008 (8) | 0.0038 (8) | 0.0003 (9) |
C1 | 0.0169 (12) | 0.0255 (13) | 0.0197 (12) | 0.0033 (11) | 0.0093 (10) | 0.0021 (10) |
C2 | 0.0222 (13) | 0.0220 (13) | 0.0293 (14) | −0.0037 (11) | 0.0094 (11) | −0.0024 (11) |
C3 | 0.0173 (12) | 0.0280 (14) | 0.0235 (13) | −0.0019 (11) | 0.0025 (10) | −0.0007 (11) |
C4 | 0.0166 (12) | 0.0208 (13) | 0.0187 (12) | 0.0011 (10) | 0.0074 (10) | 0.0024 (10) |
C5 | 0.0178 (12) | 0.0271 (14) | 0.0136 (11) | −0.0016 (10) | 0.0091 (10) | −0.0011 (10) |
C6 | 0.0214 (13) | 0.0238 (13) | 0.0185 (12) | 0.0003 (10) | 0.0084 (10) | 0.0005 (10) |
C7 | 0.0240 (13) | 0.0245 (13) | 0.0193 (12) | −0.0062 (11) | 0.0081 (10) | −0.0032 (10) |
C8 | 0.0174 (12) | 0.0335 (15) | 0.0176 (12) | −0.0044 (11) | 0.0069 (10) | −0.0035 (11) |
C9 | 0.0149 (11) | 0.0289 (14) | 0.0155 (11) | 0.0004 (10) | 0.0067 (10) | −0.0009 (10) |
C10 | 0.0173 (12) | 0.0225 (13) | 0.0207 (12) | 0.0001 (10) | 0.0081 (10) | 0.0028 (10) |
C11 | 0.0170 (12) | 0.0215 (13) | 0.0189 (11) | 0.0003 (10) | 0.0082 (10) | 0.0006 (10) |
C12 | 0.0190 (12) | 0.0235 (14) | 0.0212 (12) | 0.0023 (10) | 0.0069 (10) | 0.0024 (10) |
C13 | 0.0250 (14) | 0.0199 (13) | 0.0321 (14) | 0.0040 (11) | 0.0085 (12) | 0.0050 (11) |
C14 | 0.0273 (14) | 0.0191 (13) | 0.0420 (16) | −0.0034 (11) | 0.0094 (12) | 0.0007 (12) |
C15 | 0.0184 (12) | 0.0257 (14) | 0.0326 (14) | −0.0021 (11) | 0.0056 (11) | 0.0003 (12) |
C16 | 0.0176 (12) | 0.0215 (13) | 0.0154 (11) | 0.0012 (10) | 0.0079 (9) | 0.0011 (10) |
C17 | 0.0191 (12) | 0.0214 (13) | 0.0244 (13) | −0.0048 (10) | 0.0061 (10) | −0.0018 (11) |
O1—C1 | 1.209 (3) | C6—C7 | 1.362 (3) |
O2—C16 | 1.210 (3) | C6—H6 | 0.9500 |
O3—C16 | 1.325 (3) | C7—C8 | 1.382 (4) |
O3—C17 | 1.431 (3) | C7—H7 | 0.9500 |
N1—C8 | 1.320 (3) | C8—H8 | 0.9500 |
N1—C9 | 1.341 (3) | C10—C15 | 1.383 (4) |
N2—N3 | 1.327 (3) | C10—C11 | 1.402 (3) |
N2—C4 | 1.302 (3) | C11—C12 | 1.385 (3) |
N3—C10 | 1.373 (3) | C11—C16 | 1.468 (3) |
N3—H3N | 0.8800 | C12—C13 | 1.357 (4) |
C1—C2 | 1.460 (3) | C12—H12 | 0.9500 |
C1—C9 | 1.479 (4) | C13—C14 | 1.381 (4) |
C2—C3 | 1.335 (4) | C13—H13 | 0.9500 |
C2—H2 | 0.9500 | C14—C15 | 1.363 (4) |
C3—C4 | 1.424 (4) | C14—H14 | 0.9500 |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.455 (3) | C17—H17A | 0.9800 |
C5—C6 | 1.383 (4) | C17—H17B | 0.9800 |
C5—C9 | 1.394 (3) | C17—H17C | 0.9800 |
C16—O3—C17 | 116.24 (19) | N1—C9—C5 | 123.7 (2) |
C8—N1—C9 | 117.1 (2) | N1—C9—C1 | 116.0 (2) |
C4—N2—N3 | 119.3 (2) | C5—C9—C1 | 120.3 (2) |
N2—N3—C10 | 120.2 (2) | N3—C10—C15 | 120.9 (2) |
N2—N3—H3N | 119.9 | N3—C10—C11 | 119.8 (2) |
C10—N3—H3N | 119.9 | C15—C10—C11 | 119.2 (2) |
O1—C1—C2 | 120.5 (2) | C12—C11—C10 | 118.7 (2) |
O1—C1—C9 | 123.1 (2) | C12—C11—C16 | 120.2 (2) |
C2—C1—C9 | 116.4 (2) | C10—C11—C16 | 121.1 (2) |
C3—C2—C1 | 122.2 (2) | C13—C12—C11 | 121.6 (2) |
C3—C2—H2 | 118.9 | C13—C12—H12 | 119.2 |
C1—C2—H2 | 118.9 | C11—C12—H12 | 119.2 |
C2—C3—C4 | 122.2 (2) | C12—C13—C14 | 119.3 (2) |
C2—C3—H3 | 118.9 | C12—C13—H13 | 120.4 |
C4—C3—H3 | 118.9 | C14—C13—H13 | 120.4 |
N2—C4—C3 | 125.6 (2) | C15—C14—C13 | 120.7 (2) |
N2—C4—C5 | 115.8 (2) | C15—C14—H14 | 119.6 |
C3—C4—C5 | 118.6 (2) | C13—C14—H14 | 119.6 |
C6—C5—C9 | 117.1 (2) | C14—C15—C10 | 120.5 (2) |
C6—C5—C4 | 122.7 (2) | C14—C15—H15 | 119.8 |
C9—C5—C4 | 120.2 (2) | C10—C15—H15 | 119.8 |
C7—C6—C5 | 119.7 (2) | O2—C16—O3 | 122.8 (2) |
C7—C6—H6 | 120.1 | O2—C16—C11 | 125.2 (2) |
C5—C6—H6 | 120.1 | O3—C16—C11 | 112.0 (2) |
C6—C7—C8 | 118.9 (2) | O3—C17—H17A | 109.5 |
C6—C7—H7 | 120.6 | O3—C17—H17B | 109.5 |
C8—C7—H7 | 120.6 | H17A—C17—H17B | 109.5 |
N1—C8—C7 | 123.5 (2) | O3—C17—H17C | 109.5 |
N1—C8—H8 | 118.2 | H17A—C17—H17C | 109.5 |
C7—C8—H8 | 118.2 | H17B—C17—H17C | 109.5 |
C4—N2—N3—C10 | 178.5 (2) | O1—C1—C9—N1 | −1.1 (3) |
O1—C1—C2—C3 | 179.9 (2) | C2—C1—C9—N1 | 177.7 (2) |
C9—C1—C2—C3 | 1.1 (4) | O1—C1—C9—C5 | −179.1 (2) |
C1—C2—C3—C4 | −0.3 (4) | C2—C1—C9—C5 | −0.3 (3) |
N3—N2—C4—C3 | −0.1 (4) | N2—N3—C10—C15 | 0.9 (4) |
N3—N2—C4—C5 | −179.75 (19) | N2—N3—C10—C11 | −179.9 (2) |
C2—C3—C4—N2 | 179.2 (2) | N3—C10—C11—C12 | 179.7 (2) |
C2—C3—C4—C5 | −1.2 (4) | C15—C10—C11—C12 | −1.0 (4) |
N2—C4—C5—C6 | 3.1 (3) | N3—C10—C11—C16 | −2.1 (3) |
C3—C4—C5—C6 | −176.5 (2) | C15—C10—C11—C16 | 177.1 (2) |
N2—C4—C5—C9 | −178.3 (2) | C10—C11—C12—C13 | 0.9 (4) |
C3—C4—C5—C9 | 2.0 (3) | C16—C11—C12—C13 | −177.3 (2) |
C9—C5—C6—C7 | 0.0 (3) | C11—C12—C13—C14 | 0.3 (4) |
C4—C5—C6—C7 | 178.5 (2) | C12—C13—C14—C15 | −1.3 (4) |
C5—C6—C7—C8 | 0.3 (4) | C13—C14—C15—C10 | 1.1 (4) |
C9—N1—C8—C7 | −0.3 (4) | N3—C10—C15—C14 | 179.3 (3) |
C6—C7—C8—N1 | −0.2 (4) | C11—C10—C15—C14 | 0.1 (4) |
C8—N1—C9—C5 | 0.6 (3) | C17—O3—C16—O2 | −2.4 (3) |
C8—N1—C9—C1 | −177.3 (2) | C17—O3—C16—C11 | 177.35 (19) |
C6—C5—C9—N1 | −0.5 (3) | C12—C11—C16—O2 | −178.7 (2) |
C4—C5—C9—N1 | −179.1 (2) | C10—C11—C16—O2 | 3.2 (4) |
C6—C5—C9—C1 | 177.4 (2) | C12—C11—C16—O3 | 1.6 (3) |
C4—C5—C9—C1 | −1.2 (3) | C10—C11—C16—O3 | −176.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2 | 0.88 | 1.96 | 2.633 (3) | 132 |
C12—H12···O3 | 0.95 | 2.32 | 2.662 (3) | 101 |
C8—H8···O1i | 0.95 | 2.51 | 3.425 (3) | 161 |
C17—H17B···O1ii | 0.98 | 2.49 | 3.227 (4) | 132 |
C17—H17C···N1iii | 0.98 | 2.59 | 3.379 (3) | 138 |
Symmetry codes: (i) −x+1/2, y−1/2, −z−1/2; (ii) x+1/2, −y+5/2, z+1/2; (iii) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H13N3O3 |
Mr | 307.30 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 98 |
a, b, c (Å) | 26.695 (3), 8.2513 (9), 13.5873 (16) |
β (°) | 116.589 (5) |
V (Å3) | 2676.3 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.35 × 0.13 × 0.05 |
Data collection | |
Diffractometer | Rigaku AFC12K/SATURN724 |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.798, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4109, 2329, 2165 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.132, 1.36 |
No. of reflections | 2329 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.23 |
Computer programs: CrystalClear (Rigaku Americas Corporation, 2005), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2 | 0.88 | 1.96 | 2.633 (3) | 132 |
C12—H12···O3 | 0.95 | 2.32 | 2.662 (3) | 101 |
C8—H8···O1i | 0.95 | 2.51 | 3.425 (3) | 161 |
C17—H17B···O1ii | 0.98 | 2.49 | 3.227 (4) | 132 |
C17—H17C···N1iii | 0.98 | 2.59 | 3.379 (3) | 138 |
Symmetry codes: (i) −x+1/2, y−1/2, −z−1/2; (ii) x+1/2, −y+5/2, z+1/2; (iii) −x+1, y, −z+1/2. |
The title compound, C17H13O3N3 (I) was prepared during an on-going study of the coordination chemistry of organotin(IV) 5-[(E)-2-((aryl)-1-diazenyl)quinolin-8-olates] (Basu Baul, Mizar, Lyčka et al. (2006); Basu Baul, Mizar, Song et al. (2006).
The crystal structure shows (I), (Fig. 1), to exist as the phenylhydrazone tautomer rather than in the azo form (Sawicki, 1957). The non-H atoms in (I) are effectivlely co-planar and the dihedral angle between the N1/C1—C9 and C10—C15 ring planes is 1.33 (10)°. An intramolecular N3—H···O2 hydrogen bond contributes to the stability of the observed conformation; an intramolecular C12—H···O3 interaction is also noted. Intermolecular C8—H···O1 interactions lead to the formation of supramolecular chains aligned along the b axis (Fig. 2 & Table 1). These stack side-by-side to form layers and interactions between these layers are of the type C—H···O and C—H···N and involve the methyl groups (Fig. 3).
A very closely related molecule characterized in the tautomeric form shown in the Scheme has been observed previously in a dimeric dibenzyltin structure (Basu Baul et al., 2005).