Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020430/hb2387sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020430/hb2387Isup2.hkl |
CCDC reference: 648072
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.041
- wR factor = 0.103
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2W - H2WA ... 1.03 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C14A .. O1' .. 2.98 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: 2'-(4-dimethylaminobenzylidene)pyrazine-2-carbohydrazide (Shi & Yuan, 2006); N'-(3-ethoxy-4-hydroxybenzylidene)isonicotino-hydrazide (Qian et al., 2006); 2'-(1,3-benzodioxol-5-ylmethylene)-2-methoxybenzo- hydrazide (Jing & Yu, 2007). For background literature, see: Roma et al. (2000); Maguire et al. (1994); Zhang & Jenekhe (2000); El-Masry et al. (2000); Pandey et al. (1999); Singh et al. (1988); Hodnett et al. (1970); Desai et al. (2001); Aydogan et al. (2001); Taggi et al. (2002).
For related literature, see: Zhang & Jenekhe (2000).
A mixture of 4-hydrazino-8-(trifluoromethyl)quinoline (1.13 g, 0.005 mol) and salicylaldehyde (0.61 g, 0.005 mol) in 15 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for three hours. On cooling, the solid that separated was filtered and recrystallized from a (1:1 v/v) DMF & acetone mixture to yield crystals of (I) (m.p.: Above 523 K). Analysis for C34H34F6N6O10S: Found (Calculated): C: 48.87 (48.99); H: 4.02 (4.08); N: 10.01 (10.09): S: 3.78% (3.84%)
The hydroxyphenyl ring of one molecule is disordered over two sites by a twofold rotation. Thus, the hydroxyl group is found in both ortho positions with site occupation factors of 0.778 (5) and 0.222 (5). H atoms were found in a difference map, but those bonded to C were refined using a riding model with C—H = 0.95 Å, and Uiso(H) = 1.2Ueq(C). H atoms bonded to O were freely refined, except for the minor component of the disordered hydroxyl H atoms which was refined using a riding model with O—H = 0.84 Å, and Uiso(H) = 1.2Ueq(O). The torsion angle about the C—O bond was allowed to refine.
It is well known that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with interesting biological activities. A large variety of quinoline derivatives have been used as antimalarial, anti-inflammatory agents, antiasthmatic, antibacterial, antihypertensive and tyrokinase PDGF-RTK inhibiting agents. Furthermore, poly-substituted quinolines have been found to undergo hierarchical self-assembly into a variety of nano- and mesostructures with enhanced electronic and photonic functions.
Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions. On the industrial scale, they have wide range of applications such as dyes and pigments.
The title compound, (I), a new Schiff base was synthesized and its crystal structure has been determined. The geometric parameters for (I) are in the usual ranges. There are two organic molecules in the asymmetric unit. The dihedral angles between the mean planes of their two aromatic ring systems are 10.94 (9)° and 7.14 (8)°, respectively. The crystal packing is stabilized by many N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1).
For related structures, see: 2'-(4-dimethylaminobenzylidene)pyrazine-2-carbohydrazide (Shi & Yuan, 2006); N'-(3-ethoxy-4-hydroxybenzylidene)isonicotino-hydrazide (Qian et al., 2006); 2'-(1,3-benzodioxol-5-ylmethylene)-2-methoxybenzo- hydrazide (Jing & Yu, 2007). For background literature, see: Roma et al. (2000); Maguire et al. (1994); Zhang & Jenekhe (2000); El-Masry et al. (2000); Pandey et al. (1999); Singh et al. (1988); Hodnett et al. (1970); Desai et al. (2001); Aydogan et al. (2001); Taggi et al. (2002).
For related literature, see: Zhang & Jenekhe (2000).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.
Fig. 1. Perspective view of (I); displacement ellipsoids are at the 50% probability level (arbitrary spheres for the H atoms). |
2C17H13F3N3O+·SO42−·4H2O | Z = 2 |
Mr = 832.73 | F(000) = 860 |
Triclinic, P1 | Dx = 1.531 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.210 (2) Å | Cell parameters from 13707 reflections |
b = 12.084 (2) Å | θ = 3.5–25.1° |
c = 14.919 (3) Å | µ = 0.19 mm−1 |
α = 84.64 (4)° | T = 173 K |
β = 68.16 (4)° | Block, colourless |
γ = 74.38 (3)° | 0.24 × 0.23 × 0.19 mm |
V = 1806.6 (8) Å3 |
Stoe IPDSII two-circle diffractometer | 6759 independent reflections |
Radiation source: fine-focus sealed tube | 5130 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 25.7°, θmin = 3.4° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −13→13 |
Tmin = 0.958, Tmax = 0.968 | k = −14→14 |
25452 measured reflections | l = −18→18 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3 |
6759 reflections | (Δ/σ)max = 0.001 |
581 parameters | Δρmax = 0.22 e Å−3 |
1 restraint | Δρmin = −0.43 e Å−3 |
2C17H13F3N3O+·SO42−·4H2O | γ = 74.38 (3)° |
Mr = 832.73 | V = 1806.6 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.210 (2) Å | Mo Kα radiation |
b = 12.084 (2) Å | µ = 0.19 mm−1 |
c = 14.919 (3) Å | T = 173 K |
α = 84.64 (4)° | 0.24 × 0.23 × 0.19 mm |
β = 68.16 (4)° |
Stoe IPDSII two-circle diffractometer | 6759 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 5130 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.968 | Rint = 0.059 |
25452 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 1 restraint |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.22 e Å−3 |
6759 reflections | Δρmin = −0.43 e Å−3 |
581 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 | Occ. (<1) | |
O1 | 1.3775 (2) | −0.22947 (19) | 0.22630 (14) | 0.0412 (7) | 0.778 (5) |
H1O | 1.318 (5) | −0.172 (4) | 0.211 (3) | 0.081 (14)* | 0.778 (5) |
O1' | 1.1034 (6) | −0.2603 (7) | 0.5458 (5) | 0.052 (3) | 0.222 (5) |
H1' | 1.0558 | −0.2007 | 0.5307 | 0.062* | 0.222 (5) |
N1 | 0.52896 (17) | 0.09054 (14) | 0.60698 (12) | 0.0243 (3) | |
H1 | 0.454 (3) | 0.116 (2) | 0.6551 (18) | 0.039 (7)* | |
N2 | 0.90860 (16) | −0.03268 (14) | 0.40931 (13) | 0.0241 (3) | |
H2 | 0.932 (2) | −0.0153 (19) | 0.3513 (17) | 0.027 (6)* | |
N3 | 1.00050 (15) | −0.11454 (14) | 0.43810 (12) | 0.0256 (4) | |
F1 | 0.31984 (13) | 0.33610 (11) | 0.61261 (10) | 0.0474 (4) | |
F2 | 0.23127 (13) | 0.30820 (15) | 0.51411 (10) | 0.0577 (4) | |
F3 | 0.26362 (11) | 0.17934 (11) | 0.61711 (9) | 0.0396 (3) | |
C1 | 0.62302 (19) | 0.01488 (17) | 0.63286 (14) | 0.0265 (4) | |
H1B | 0.6005 | −0.0089 | 0.6983 | 0.032* | |
C2 | 0.74900 (19) | −0.02940 (16) | 0.56998 (13) | 0.0252 (4) | |
H2B | 0.8118 | −0.0832 | 0.5914 | 0.030* | |
C3 | 0.78468 (18) | 0.00583 (15) | 0.47277 (13) | 0.0213 (4) | |
C4 | 0.68345 (18) | 0.08474 (15) | 0.44273 (13) | 0.0222 (4) | |
C5 | 0.55447 (18) | 0.12711 (16) | 0.51282 (13) | 0.0218 (4) | |
C6 | 0.45417 (19) | 0.20490 (16) | 0.48440 (14) | 0.0258 (4) | |
C7 | 0.4832 (2) | 0.23695 (19) | 0.38910 (15) | 0.0335 (5) | |
H7 | 0.4167 | 0.2892 | 0.3703 | 0.040* | |
C8 | 0.6095 (2) | 0.1934 (2) | 0.31951 (15) | 0.0383 (5) | |
H8 | 0.6270 | 0.2148 | 0.2538 | 0.046* | |
C9 | 0.7080 (2) | 0.12030 (19) | 0.34560 (14) | 0.0308 (4) | |
H9 | 0.7937 | 0.0931 | 0.2980 | 0.037* | |
C10 | 0.3180 (2) | 0.25691 (18) | 0.55618 (15) | 0.0301 (4) | |
C11 | 1.11525 (19) | −0.14833 (17) | 0.37231 (14) | 0.0272 (4) | |
H11 | 1.1313 | −0.1141 | 0.3103 | 0.033* | |
C12 | 1.22281 (19) | −0.23742 (16) | 0.38853 (14) | 0.0250 (4) | |
C13 | 1.3457 (2) | −0.27358 (18) | 0.31309 (15) | 0.0308 (4) | |
H13 | 1.3620 | −0.2358 | 0.2526 | 0.037* | 0.222 (5) |
C14 | 1.4443 (2) | −0.3651 (2) | 0.32688 (18) | 0.0395 (5) | |
H14 | 1.5272 | −0.3896 | 0.2755 | 0.047* | |
C15 | 1.4219 (2) | −0.4200 (2) | 0.41452 (18) | 0.0428 (6) | |
H15 | 1.4887 | −0.4834 | 0.4226 | 0.051* | |
C16 | 1.3023 (2) | −0.3834 (2) | 0.49132 (18) | 0.0432 (6) | |
H16 | 1.2880 | −0.4202 | 0.5522 | 0.052* | |
C17 | 1.2044 (2) | −0.29276 (18) | 0.47793 (16) | 0.0339 (5) | |
H17 | 1.1229 | −0.2675 | 0.5304 | 0.041* | 0.778 (5) |
O1A | 0.32607 (15) | 0.20844 (12) | 0.20878 (11) | 0.0347 (3) | |
H1OA | 0.269 (3) | 0.169 (2) | 0.219 (2) | 0.052 (8)* | |
N1A | 0.85453 (16) | 0.67791 (15) | −0.06464 (11) | 0.0249 (3) | |
H1A | 0.892 (2) | 0.732 (2) | −0.0841 (17) | 0.037 (7)* | |
N2A | 0.64348 (17) | 0.43207 (15) | 0.04510 (12) | 0.0271 (4) | |
H2A | 0.676 (2) | 0.358 (2) | 0.0356 (17) | 0.036 (6)* | |
N3A | 0.51353 (16) | 0.46623 (14) | 0.11072 (11) | 0.0272 (4) | |
F1A | 1.26581 (13) | 0.57259 (14) | −0.23741 (11) | 0.0570 (4) | |
F2A | 1.09414 (14) | 0.68921 (14) | −0.25668 (10) | 0.0513 (4) | |
F3A | 1.12818 (13) | 0.69213 (13) | −0.12537 (9) | 0.0452 (3) | |
C1A | 0.72595 (18) | 0.70800 (17) | −0.00552 (13) | 0.0253 (4) | |
H1A1 | 0.6845 | 0.7869 | 0.0101 | 0.030* | |
C2A | 0.65299 (19) | 0.62951 (17) | 0.03271 (13) | 0.0255 (4) | |
H2A1 | 0.5631 | 0.6539 | 0.0750 | 0.031* | |
C3A | 0.71164 (19) | 0.51209 (16) | 0.00923 (13) | 0.0243 (4) | |
C4A | 0.85016 (19) | 0.47867 (17) | −0.05538 (13) | 0.0254 (4) | |
C5A | 0.92011 (19) | 0.56478 (17) | −0.09054 (13) | 0.0249 (4) | |
C6A | 1.0574 (2) | 0.53261 (19) | −0.15102 (13) | 0.0309 (5) | |
C7A | 1.1190 (2) | 0.4183 (2) | −0.17435 (15) | 0.0387 (5) | |
H7A | 1.2107 | 0.3967 | −0.2134 | 0.046* | |
C8A | 1.0493 (2) | 0.3342 (2) | −0.14170 (16) | 0.0411 (6) | |
H8A | 1.0935 | 0.2562 | −0.1595 | 0.049* | |
C9A | 0.9176 (2) | 0.36283 (18) | −0.08410 (15) | 0.0344 (5) | |
H9A | 0.8710 | 0.3046 | −0.0631 | 0.041* | |
C10A | 1.1356 (2) | 0.6208 (2) | −0.19247 (14) | 0.0339 (5) | |
C11A | 0.4553 (2) | 0.38410 (17) | 0.14187 (14) | 0.0277 (4) | |
H11A | 0.5008 | 0.3080 | 0.1185 | 0.033* | |
C12A | 0.3197 (2) | 0.40731 (17) | 0.21290 (14) | 0.0269 (4) | |
C13A | 0.2583 (2) | 0.31612 (17) | 0.24648 (15) | 0.0288 (4) | |
C14A | 0.1308 (2) | 0.33696 (19) | 0.31723 (16) | 0.0346 (5) | |
H14A | 0.0902 | 0.2752 | 0.3409 | 0.042* | |
C15A | 0.0632 (2) | 0.4472 (2) | 0.35304 (18) | 0.0400 (5) | |
H15A | −0.0232 | 0.4605 | 0.4014 | 0.048* | |
C16A | 0.1210 (2) | 0.5386 (2) | 0.31869 (18) | 0.0407 (5) | |
H16A | 0.0739 | 0.6143 | 0.3425 | 0.049* | |
C17A | 0.2477 (2) | 0.51808 (19) | 0.24951 (16) | 0.0340 (5) | |
H17A | 0.2871 | 0.5806 | 0.2262 | 0.041* | |
S1 | 0.86919 (5) | 0.97050 (4) | 0.84026 (3) | 0.02299 (12) | |
O1S | 0.98907 (14) | 1.01484 (12) | 0.79747 (10) | 0.0305 (3) | |
O2S | 0.87614 (14) | 0.89968 (12) | 0.92511 (10) | 0.0322 (3) | |
O3S | 0.85853 (15) | 0.90418 (13) | 0.76706 (10) | 0.0355 (3) | |
O4S | 0.75019 (14) | 1.07005 (13) | 0.87035 (11) | 0.0379 (4) | |
O1W | 0.2831 (2) | 0.81279 (15) | 0.96894 (15) | 0.0537 (5) | |
H1WA | 0.280 (3) | 0.843 (3) | 1.019 (3) | 0.069 (10)* | |
H1WB | 0.239 (4) | 0.863 (3) | 0.938 (3) | 0.084 (11)* | |
O2W | 0.50009 (19) | 0.0371 (2) | 0.89926 (14) | 0.0581 (5) | |
H2WA | 0.521 (8) | −0.051 (8) | 0.906 (6) | 0.26 (4)* | |
H2WB | 0.582 (4) | 0.054 (3) | 0.893 (3) | 0.095 (12)* | |
O3W | 0.15544 (16) | 0.01500 (14) | 0.89528 (12) | 0.0356 (4) | |
H3WA | 0.125 (3) | 0.047 (3) | 0.949 (3) | 0.069 (10)* | |
H3WB | 0.091 (3) | 0.022 (3) | 0.873 (2) | 0.069 (9)* | |
O4W | 0.34561 (17) | 0.13431 (16) | 0.78822 (11) | 0.0397 (4) | |
H4WA | 0.395 (4) | 0.111 (3) | 0.818 (3) | 0.089 (13)* | |
H4WB | 0.283 (4) | 0.093 (3) | 0.817 (2) | 0.074 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0259 (11) | 0.0488 (13) | 0.0276 (11) | 0.0117 (9) | −0.0022 (8) | 0.0072 (9) |
O1' | 0.019 (4) | 0.076 (6) | 0.032 (4) | 0.010 (3) | 0.000 (3) | 0.031 (4) |
N1 | 0.0198 (8) | 0.0262 (8) | 0.0223 (8) | −0.0021 (7) | −0.0045 (7) | −0.0034 (7) |
N2 | 0.0205 (8) | 0.0259 (9) | 0.0237 (9) | −0.0008 (7) | −0.0095 (7) | 0.0012 (7) |
N3 | 0.0200 (8) | 0.0256 (8) | 0.0309 (9) | 0.0001 (7) | −0.0127 (7) | −0.0009 (7) |
F1 | 0.0396 (8) | 0.0431 (8) | 0.0521 (8) | −0.0084 (6) | −0.0038 (6) | −0.0251 (6) |
F2 | 0.0277 (7) | 0.0840 (11) | 0.0456 (8) | 0.0193 (7) | −0.0176 (6) | −0.0047 (7) |
F3 | 0.0223 (6) | 0.0421 (7) | 0.0479 (7) | −0.0074 (5) | −0.0047 (6) | −0.0049 (6) |
C1 | 0.0263 (10) | 0.0266 (10) | 0.0238 (9) | −0.0029 (8) | −0.0089 (8) | 0.0013 (8) |
C2 | 0.0240 (10) | 0.0240 (10) | 0.0257 (10) | −0.0005 (8) | −0.0108 (8) | 0.0004 (8) |
C3 | 0.0195 (9) | 0.0190 (9) | 0.0262 (9) | −0.0032 (7) | −0.0096 (8) | −0.0031 (7) |
C4 | 0.0218 (9) | 0.0218 (9) | 0.0236 (9) | −0.0039 (7) | −0.0098 (8) | −0.0014 (7) |
C5 | 0.0207 (9) | 0.0215 (9) | 0.0247 (9) | −0.0035 (7) | −0.0101 (8) | −0.0042 (7) |
C6 | 0.0225 (10) | 0.0261 (10) | 0.0297 (10) | −0.0015 (8) | −0.0125 (8) | −0.0050 (8) |
C7 | 0.0270 (11) | 0.0377 (12) | 0.0351 (11) | 0.0020 (9) | −0.0177 (9) | 0.0014 (9) |
C8 | 0.0310 (12) | 0.0522 (14) | 0.0257 (11) | 0.0006 (10) | −0.0123 (9) | 0.0044 (10) |
C9 | 0.0219 (10) | 0.0393 (12) | 0.0249 (10) | −0.0009 (9) | −0.0065 (8) | 0.0014 (9) |
C10 | 0.0253 (10) | 0.0312 (11) | 0.0346 (11) | −0.0002 (9) | −0.0155 (9) | −0.0043 (9) |
C11 | 0.0245 (10) | 0.0267 (10) | 0.0283 (10) | −0.0016 (8) | −0.0104 (8) | 0.0002 (8) |
C12 | 0.0215 (10) | 0.0213 (9) | 0.0331 (10) | 0.0000 (8) | −0.0140 (8) | −0.0032 (8) |
C13 | 0.0257 (10) | 0.0313 (11) | 0.0346 (11) | 0.0006 (8) | −0.0143 (9) | −0.0047 (9) |
C14 | 0.0270 (11) | 0.0409 (12) | 0.0478 (13) | 0.0072 (9) | −0.0181 (10) | −0.0140 (11) |
C15 | 0.0383 (13) | 0.0344 (12) | 0.0598 (15) | 0.0068 (10) | −0.0331 (12) | −0.0010 (11) |
C16 | 0.0420 (14) | 0.0413 (13) | 0.0506 (14) | −0.0050 (11) | −0.0278 (12) | 0.0109 (11) |
C17 | 0.0287 (12) | 0.0332 (11) | 0.0401 (12) | −0.0039 (9) | −0.0162 (10) | 0.0028 (9) |
O1A | 0.0327 (8) | 0.0241 (7) | 0.0488 (9) | −0.0058 (6) | −0.0182 (7) | 0.0030 (6) |
N1A | 0.0222 (8) | 0.0281 (9) | 0.0211 (8) | −0.0020 (7) | −0.0075 (7) | 0.0021 (7) |
N2A | 0.0290 (9) | 0.0226 (9) | 0.0272 (9) | −0.0015 (7) | −0.0104 (7) | −0.0013 (7) |
N3A | 0.0249 (9) | 0.0294 (9) | 0.0261 (8) | −0.0041 (7) | −0.0097 (7) | −0.0008 (7) |
F1A | 0.0204 (7) | 0.0686 (10) | 0.0597 (9) | −0.0010 (6) | 0.0036 (6) | −0.0009 (8) |
F2A | 0.0483 (8) | 0.0716 (10) | 0.0438 (8) | −0.0236 (7) | −0.0285 (7) | 0.0298 (7) |
F3A | 0.0381 (7) | 0.0619 (9) | 0.0347 (7) | −0.0152 (6) | −0.0101 (6) | −0.0003 (6) |
C1A | 0.0216 (9) | 0.0273 (10) | 0.0219 (9) | 0.0025 (8) | −0.0072 (8) | −0.0039 (8) |
C2A | 0.0195 (9) | 0.0280 (10) | 0.0220 (9) | 0.0016 (8) | −0.0047 (8) | −0.0020 (8) |
C3A | 0.0255 (10) | 0.0271 (10) | 0.0186 (9) | 0.0008 (8) | −0.0111 (8) | −0.0002 (7) |
C4A | 0.0256 (10) | 0.0279 (10) | 0.0165 (9) | 0.0040 (8) | −0.0080 (8) | −0.0005 (7) |
C5A | 0.0236 (10) | 0.0298 (10) | 0.0153 (8) | 0.0042 (8) | −0.0085 (8) | 0.0018 (7) |
C6A | 0.0237 (10) | 0.0427 (12) | 0.0183 (9) | 0.0035 (9) | −0.0074 (8) | 0.0012 (8) |
C7A | 0.0270 (11) | 0.0473 (13) | 0.0244 (10) | 0.0120 (10) | −0.0044 (9) | −0.0017 (9) |
C8A | 0.0408 (13) | 0.0332 (12) | 0.0311 (11) | 0.0118 (10) | −0.0063 (10) | −0.0039 (9) |
C9A | 0.0369 (12) | 0.0288 (11) | 0.0268 (10) | 0.0049 (9) | −0.0083 (9) | −0.0014 (8) |
C10A | 0.0209 (10) | 0.0493 (13) | 0.0221 (10) | 0.0024 (9) | −0.0059 (8) | 0.0034 (9) |
C11A | 0.0319 (11) | 0.0258 (10) | 0.0311 (10) | −0.0060 (8) | −0.0193 (9) | 0.0027 (8) |
C12A | 0.0292 (10) | 0.0281 (10) | 0.0298 (10) | −0.0076 (8) | −0.0178 (9) | 0.0015 (8) |
C13A | 0.0312 (11) | 0.0266 (10) | 0.0364 (11) | −0.0063 (8) | −0.0227 (9) | 0.0040 (8) |
C14A | 0.0302 (11) | 0.0342 (11) | 0.0446 (12) | −0.0119 (9) | −0.0174 (10) | 0.0034 (9) |
C15A | 0.0270 (11) | 0.0438 (13) | 0.0490 (14) | −0.0090 (10) | −0.0117 (10) | −0.0068 (11) |
C16A | 0.0344 (12) | 0.0354 (12) | 0.0531 (14) | −0.0068 (10) | −0.0147 (11) | −0.0140 (10) |
C17A | 0.0348 (12) | 0.0307 (11) | 0.0418 (12) | −0.0116 (9) | −0.0168 (10) | −0.0027 (9) |
S1 | 0.0192 (2) | 0.0248 (2) | 0.0228 (2) | −0.00320 (18) | −0.00665 (18) | −0.00071 (18) |
O1S | 0.0268 (7) | 0.0397 (8) | 0.0277 (7) | −0.0130 (6) | −0.0113 (6) | 0.0064 (6) |
O2S | 0.0354 (8) | 0.0335 (8) | 0.0252 (7) | −0.0094 (6) | −0.0085 (6) | 0.0039 (6) |
O3S | 0.0429 (9) | 0.0366 (8) | 0.0314 (8) | −0.0144 (7) | −0.0143 (7) | −0.0036 (6) |
O4S | 0.0277 (8) | 0.0406 (9) | 0.0373 (8) | 0.0068 (7) | −0.0120 (7) | −0.0061 (7) |
O1W | 0.0787 (14) | 0.0294 (9) | 0.0528 (11) | 0.0094 (9) | −0.0367 (11) | −0.0120 (8) |
O2W | 0.0390 (10) | 0.0758 (14) | 0.0551 (11) | −0.0068 (10) | −0.0198 (9) | 0.0093 (10) |
O3W | 0.0351 (9) | 0.0434 (9) | 0.0304 (8) | −0.0074 (7) | −0.0153 (7) | −0.0025 (7) |
O4W | 0.0249 (8) | 0.0587 (11) | 0.0285 (8) | −0.0048 (8) | −0.0051 (7) | −0.0025 (7) |
O1—C13 | 1.311 (3) | N2A—C3A | 1.343 (3) |
O1—H1O | 0.90 (5) | N2A—N3A | 1.393 (2) |
O1'—C17 | 1.201 (6) | N2A—H2A | 0.88 (3) |
O1'—H1' | 0.8400 | N3A—C11A | 1.290 (3) |
N1—C1 | 1.347 (3) | F1A—C10A | 1.344 (2) |
N1—C5 | 1.380 (3) | F2A—C10A | 1.339 (2) |
N1—H1 | 0.88 (3) | F3A—C10A | 1.346 (3) |
N2—C3 | 1.341 (3) | C1A—C2A | 1.365 (3) |
N2—N3 | 1.388 (2) | C1A—H1A1 | 0.9500 |
N2—H2 | 0.83 (2) | C2A—C3A | 1.410 (3) |
N3—C11 | 1.280 (3) | C2A—H2A1 | 0.9500 |
F1—C10 | 1.341 (2) | C3A—C4A | 1.458 (3) |
F2—C10 | 1.335 (2) | C4A—C5A | 1.416 (3) |
F3—C10 | 1.347 (3) | C4A—C9A | 1.420 (3) |
C1—C2 | 1.365 (3) | C5A—C6A | 1.430 (3) |
C1—H1B | 0.9500 | C6A—C7A | 1.380 (3) |
C2—C3 | 1.410 (3) | C6A—C10A | 1.505 (3) |
C2—H2B | 0.9500 | C7A—C8A | 1.389 (4) |
C3—C4 | 1.454 (3) | C7A—H7A | 0.9500 |
C4—C9 | 1.418 (3) | C8A—C9A | 1.369 (3) |
C4—C5 | 1.422 (3) | C8A—H8A | 0.9500 |
C5—C6 | 1.428 (3) | C9A—H9A | 0.9500 |
C6—C7 | 1.378 (3) | C11A—C12A | 1.463 (3) |
C6—C10 | 1.505 (3) | C11A—H11A | 0.9500 |
C7—C8 | 1.402 (3) | C12A—C17A | 1.403 (3) |
C7—H7 | 0.9500 | C12A—C13A | 1.410 (3) |
C8—C9 | 1.371 (3) | C13A—C14A | 1.398 (3) |
C8—H8 | 0.9500 | C14A—C15A | 1.387 (3) |
C9—H9 | 0.9500 | C14A—H14A | 0.9500 |
C11—C12 | 1.463 (3) | C15A—C16A | 1.391 (3) |
C11—H11 | 0.9500 | C15A—H15A | 0.9500 |
C12—C13 | 1.404 (3) | C16A—C17A | 1.383 (3) |
C12—C17 | 1.404 (3) | C16A—H16A | 0.9500 |
C13—C14 | 1.399 (3) | C17A—H17A | 0.9500 |
C13—H13 | 0.9500 | S1—O3S | 1.4701 (15) |
C14—C15 | 1.377 (4) | S1—O2S | 1.4752 (15) |
C14—H14 | 0.9500 | S1—O1S | 1.4786 (15) |
C15—C16 | 1.392 (4) | S1—O4S | 1.4897 (16) |
C15—H15 | 0.9500 | O1W—H1WA | 0.85 (3) |
C16—C17 | 1.386 (3) | O1W—H1WB | 0.88 (4) |
C16—H16 | 0.9500 | O2W—H2WA | 1.04 (9) |
C17—H17 | 0.9500 | O2W—H2WB | 0.96 (4) |
O1A—C13A | 1.369 (3) | O3W—H3WA | 0.83 (4) |
O1A—H1OA | 0.86 (3) | O3W—H3WB | 0.88 (4) |
N1A—C1A | 1.349 (3) | O4W—H4WA | 0.81 (4) |
N1A—C5A | 1.380 (3) | O4W—H4WB | 0.91 (4) |
N1A—H1A | 0.85 (3) | ||
C13—O1—H1O | 120 (3) | C5A—N1A—H1A | 122.5 (17) |
C17—O1'—H1' | 109.5 | C3A—N2A—N3A | 118.62 (17) |
C1—N1—C5 | 121.24 (17) | C3A—N2A—H2A | 125.6 (16) |
C1—N1—H1 | 114.2 (16) | N3A—N2A—H2A | 115.5 (16) |
C5—N1—H1 | 124.5 (16) | C11A—N3A—N2A | 114.67 (17) |
C3—N2—N3 | 119.40 (17) | N1A—C1A—C2A | 122.61 (18) |
C3—N2—H2 | 123.2 (16) | N1A—C1A—H1A1 | 118.7 |
N3—N2—H2 | 117.1 (16) | C2A—C1A—H1A1 | 118.7 |
C11—N3—N2 | 115.17 (17) | C1A—C2A—C3A | 119.73 (18) |
N1—C1—C2 | 123.41 (18) | C1A—C2A—H2A1 | 120.1 |
N1—C1—H1B | 118.3 | C3A—C2A—H2A1 | 120.1 |
C2—C1—H1B | 118.3 | N2A—C3A—C2A | 121.69 (18) |
C1—C2—C3 | 119.09 (18) | N2A—C3A—C4A | 120.16 (17) |
C1—C2—H2B | 120.5 | C2A—C3A—C4A | 118.16 (18) |
C3—C2—H2B | 120.5 | C5A—C4A—C9A | 118.79 (18) |
N2—C3—C2 | 121.02 (17) | C5A—C4A—C3A | 118.82 (17) |
N2—C3—C4 | 120.64 (17) | C9A—C4A—C3A | 122.40 (19) |
C2—C3—C4 | 118.34 (17) | N1A—C5A—C4A | 119.19 (17) |
C9—C4—C5 | 118.53 (17) | N1A—C5A—C6A | 121.44 (19) |
C9—C4—C3 | 122.43 (17) | C4A—C5A—C6A | 119.36 (18) |
C5—C4—C3 | 119.04 (17) | C7A—C6A—C5A | 119.4 (2) |
N1—C5—C4 | 118.83 (17) | C7A—C6A—C10A | 119.03 (19) |
N1—C5—C6 | 121.51 (17) | C5A—C6A—C10A | 121.59 (19) |
C4—C5—C6 | 119.66 (17) | C6A—C7A—C8A | 121.2 (2) |
C7—C6—C5 | 119.53 (18) | C6A—C7A—H7A | 119.4 |
C7—C6—C10 | 118.45 (18) | C8A—C7A—H7A | 119.4 |
C5—C6—C10 | 121.99 (17) | C9A—C8A—C7A | 120.6 (2) |
C6—C7—C8 | 120.90 (19) | C9A—C8A—H8A | 119.7 |
C6—C7—H7 | 119.5 | C7A—C8A—H8A | 119.7 |
C8—C7—H7 | 119.5 | C8A—C9A—C4A | 120.7 (2) |
C9—C8—C7 | 120.48 (19) | C8A—C9A—H9A | 119.7 |
C9—C8—H8 | 119.8 | C4A—C9A—H9A | 119.7 |
C7—C8—H8 | 119.8 | F2A—C10A—F1A | 106.92 (17) |
C8—C9—C4 | 120.88 (19) | F2A—C10A—F3A | 105.39 (18) |
C8—C9—H9 | 119.6 | F1A—C10A—F3A | 105.61 (17) |
C4—C9—H9 | 119.6 | F2A—C10A—C6A | 112.75 (17) |
F2—C10—F1 | 106.85 (17) | F1A—C10A—C6A | 112.27 (19) |
F2—C10—F3 | 105.94 (17) | F3A—C10A—C6A | 113.31 (16) |
F1—C10—F3 | 105.51 (16) | N3A—C11A—C12A | 120.48 (18) |
F2—C10—C6 | 112.75 (17) | N3A—C11A—H11A | 119.8 |
F1—C10—C6 | 112.05 (16) | C12A—C11A—H11A | 119.8 |
F3—C10—C6 | 113.18 (17) | C17A—C12A—C13A | 118.32 (19) |
N3—C11—C12 | 122.74 (18) | C17A—C12A—C11A | 122.14 (19) |
N3—C11—H11 | 118.6 | C13A—C12A—C11A | 119.54 (18) |
C12—C11—H11 | 118.6 | O1A—C13A—C14A | 121.48 (19) |
C13—C12—C17 | 118.20 (18) | O1A—C13A—C12A | 118.72 (19) |
C13—C12—C11 | 120.45 (18) | C14A—C13A—C12A | 119.80 (19) |
C17—C12—C11 | 121.28 (18) | C15A—C14A—C13A | 120.4 (2) |
O1—C13—C14 | 114.9 (2) | C15A—C14A—H14A | 119.8 |
O1—C13—C12 | 125.01 (19) | C13A—C14A—H14A | 119.8 |
C14—C13—C12 | 120.1 (2) | C14A—C15A—C16A | 120.5 (2) |
C14—C13—H13 | 119.9 | C14A—C15A—H15A | 119.8 |
C12—C13—H13 | 119.9 | C16A—C15A—H15A | 119.8 |
C15—C14—C13 | 120.4 (2) | C17A—C16A—C15A | 119.3 (2) |
C15—C14—H14 | 119.8 | C17A—C16A—H16A | 120.4 |
C13—C14—H14 | 119.8 | C15A—C16A—H16A | 120.4 |
C14—C15—C16 | 120.6 (2) | C16A—C17A—C12A | 121.7 (2) |
C14—C15—H15 | 119.7 | C16A—C17A—H17A | 119.2 |
C16—C15—H15 | 119.7 | C12A—C17A—H17A | 119.2 |
C17—C16—C15 | 119.2 (2) | O3S—S1—O2S | 111.38 (9) |
C17—C16—H16 | 120.4 | O3S—S1—O1S | 109.47 (9) |
C15—C16—H16 | 120.4 | O2S—S1—O1S | 109.60 (9) |
O1'—C17—C16 | 118.2 (4) | O3S—S1—O4S | 108.09 (9) |
O1'—C17—C12 | 120.3 (4) | O2S—S1—O4S | 109.72 (9) |
C16—C17—C12 | 121.5 (2) | O1S—S1—O4S | 108.52 (9) |
C16—C17—H17 | 119.3 | H1WA—O1W—H1WB | 111 (3) |
C12—C17—H17 | 119.3 | H2WA—O2W—H2WB | 103 (5) |
C13A—O1A—H1OA | 107.9 (19) | H3WA—O3W—H3WB | 110 (3) |
C1A—N1A—C5A | 121.48 (18) | H4WA—O4W—H4WB | 101 (3) |
C1A—N1A—H1A | 116.0 (17) | ||
C3—N2—N3—C11 | 178.41 (17) | C11—C12—C17—C16 | 174.8 (2) |
C5—N1—C1—C2 | 1.1 (3) | C3A—N2A—N3A—C11A | −179.78 (16) |
N1—C1—C2—C3 | 0.7 (3) | C5A—N1A—C1A—C2A | 0.4 (3) |
N3—N2—C3—C2 | 4.5 (3) | N1A—C1A—C2A—C3A | −1.1 (3) |
N3—N2—C3—C4 | −175.15 (15) | N3A—N2A—C3A—C2A | −3.1 (3) |
C1—C2—C3—N2 | 177.82 (17) | N3A—N2A—C3A—C4A | 176.57 (15) |
C1—C2—C3—C4 | −2.5 (3) | C1A—C2A—C3A—N2A | −179.91 (17) |
N2—C3—C4—C9 | 3.0 (3) | C1A—C2A—C3A—C4A | 0.4 (3) |
C2—C3—C4—C9 | −176.66 (17) | N2A—C3A—C4A—C5A | −178.81 (16) |
N2—C3—C4—C5 | −177.67 (16) | C2A—C3A—C4A—C5A | 0.9 (2) |
C2—C3—C4—C5 | 2.6 (2) | N2A—C3A—C4A—C9A | 1.0 (3) |
C1—N1—C5—C4 | −0.9 (3) | C2A—C3A—C4A—C9A | −179.33 (18) |
C1—N1—C5—C6 | 178.29 (17) | C1A—N1A—C5A—C4A | 1.0 (3) |
C9—C4—C5—N1 | 178.35 (16) | C1A—N1A—C5A—C6A | −178.22 (17) |
C3—C4—C5—N1 | −1.0 (2) | C9A—C4A—C5A—N1A | 178.65 (17) |
C9—C4—C5—C6 | −0.9 (3) | C3A—C4A—C5A—N1A | −1.6 (3) |
C3—C4—C5—C6 | 179.83 (16) | C9A—C4A—C5A—C6A | −2.1 (3) |
N1—C5—C6—C7 | −178.44 (18) | C3A—C4A—C5A—C6A | 177.65 (16) |
C4—C5—C6—C7 | 0.7 (3) | N1A—C5A—C6A—C7A | 179.49 (18) |
N1—C5—C6—C10 | 3.8 (3) | C4A—C5A—C6A—C7A | 0.3 (3) |
C4—C5—C6—C10 | −177.00 (17) | N1A—C5A—C6A—C10A | −2.4 (3) |
C5—C6—C7—C8 | 0.6 (3) | C4A—C5A—C6A—C10A | 178.40 (17) |
C10—C6—C7—C8 | 178.4 (2) | C5A—C6A—C7A—C8A | 1.3 (3) |
C6—C7—C8—C9 | −1.8 (4) | C10A—C6A—C7A—C8A | −176.86 (19) |
C7—C8—C9—C4 | 1.7 (3) | C6A—C7A—C8A—C9A | −1.0 (3) |
C5—C4—C9—C8 | −0.3 (3) | C7A—C8A—C9A—C4A | −1.0 (3) |
C3—C4—C9—C8 | 178.94 (19) | C5A—C4A—C9A—C8A | 2.5 (3) |
C7—C6—C10—F2 | 14.8 (3) | C3A—C4A—C9A—C8A | −177.29 (19) |
C5—C6—C10—F2 | −167.38 (17) | C7A—C6A—C10A—F2A | 111.4 (2) |
C7—C6—C10—F1 | −105.8 (2) | C5A—C6A—C10A—F2A | −66.7 (2) |
C5—C6—C10—F1 | 72.0 (2) | C7A—C6A—C10A—F1A | −9.4 (3) |
C7—C6—C10—F3 | 135.07 (19) | C5A—C6A—C10A—F1A | 172.50 (17) |
C5—C6—C10—F3 | −47.2 (2) | C7A—C6A—C10A—F3A | −128.9 (2) |
N2—N3—C11—C12 | −177.54 (16) | C5A—C6A—C10A—F3A | 53.0 (2) |
N3—C11—C12—C13 | 178.24 (18) | N2A—N3A—C11A—C12A | 178.52 (15) |
N3—C11—C12—C17 | 1.3 (3) | N3A—C11A—C12A—C17A | 0.3 (3) |
C17—C12—C13—O1 | −179.4 (2) | N3A—C11A—C12A—C13A | −179.57 (17) |
C11—C12—C13—O1 | 3.6 (3) | C17A—C12A—C13A—O1A | 177.83 (17) |
C17—C12—C13—C14 | 2.2 (3) | C11A—C12A—C13A—O1A | −2.3 (3) |
C11—C12—C13—C14 | −174.81 (18) | C17A—C12A—C13A—C14A | −2.4 (3) |
O1—C13—C14—C15 | −178.9 (2) | C11A—C12A—C13A—C14A | 177.42 (17) |
C12—C13—C14—C15 | −0.3 (3) | O1A—C13A—C14A—C15A | −178.85 (19) |
C13—C14—C15—C16 | −1.7 (3) | C12A—C13A—C14A—C15A | 1.4 (3) |
C14—C15—C16—C17 | 1.7 (4) | C13A—C14A—C15A—C16A | 0.4 (3) |
C15—C16—C17—O1' | −177.9 (6) | C14A—C15A—C16A—C17A | −1.1 (4) |
C15—C16—C17—C12 | 0.3 (3) | C15A—C16A—C17A—C12A | 0.0 (3) |
C13—C12—C17—O1' | 175.9 (6) | C13A—C12A—C17A—C16A | 1.7 (3) |
C11—C12—C17—O1' | −7.1 (6) | C11A—C12A—C17A—C16A | −178.12 (19) |
C13—C12—C17—C16 | −2.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4Si | 0.90 (5) | 1.87 (5) | 2.715 (3) | 156 (4) |
O1′—H1′···N3 | 0.84 | 1.84 | 2.602 (7) | 149 |
N1—H1···O4W | 0.88 (3) | 1.90 (3) | 2.713 (3) | 153 (2) |
N2—H2···O1Si | 0.83 (2) | 2.06 (2) | 2.873 (2) | 166 (2) |
O1A—H1OA···O3Sii | 0.86 (3) | 1.81 (3) | 2.671 (2) | 175 (3) |
N1A—H1A···O2Siii | 0.85 (3) | 2.00 (3) | 2.740 (2) | 146 (2) |
N2A—H2A···O1Wii | 0.88 (3) | 1.99 (3) | 2.855 (3) | 169 (2) |
O1W—H1WA···O4Siv | 0.85 (3) | 1.92 (4) | 2.752 (3) | 170 (3) |
O1W—H1WB···O3Wv | 0.88 (4) | 1.99 (4) | 2.831 (3) | 158 (3) |
O2W—H2WA···O1Avi | 1.04 (9) | 2.48 (9) | 3.262 (3) | 132 (6) |
O2W—H2WB···O4Svii | 0.96 (4) | 1.85 (4) | 2.806 (3) | 173 (3) |
O3W—H3WA···O2Sviii | 0.83 (4) | 2.03 (4) | 2.825 (2) | 158 (3) |
O3W—H3WB···O1Six | 0.88 (4) | 1.91 (4) | 2.763 (2) | 165 (3) |
O4W—H4WA···O2W | 0.81 (4) | 1.99 (4) | 2.793 (3) | 171 (4) |
O4W—H4WB···O3W | 0.91 (4) | 1.90 (4) | 2.805 (3) | 170 (3) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+1, −y+2, −z+2; (v) x, y+1, z; (vi) −x+1, −y, −z+1; (vii) x, y−1, z; (viii) −x+1, −y+1, −z+2; (ix) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | 2C17H13F3N3O+·SO42−·4H2O |
Mr | 832.73 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 11.210 (2), 12.084 (2), 14.919 (3) |
α, β, γ (°) | 84.64 (4), 68.16 (4), 74.38 (3) |
V (Å3) | 1806.6 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.24 × 0.23 × 0.19 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.958, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25452, 6759, 5130 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.103, 0.99 |
No. of reflections | 6759 |
No. of parameters | 581 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.43 |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4Si | 0.90 (5) | 1.87 (5) | 2.715 (3) | 156 (4) |
O1'—H1'···N3 | 0.84 | 1.84 | 2.602 (7) | 149 |
N1—H1···O4W | 0.88 (3) | 1.90 (3) | 2.713 (3) | 153 (2) |
N2—H2···O1Si | 0.83 (2) | 2.06 (2) | 2.873 (2) | 166 (2) |
O1A—H1OA···O3Sii | 0.86 (3) | 1.81 (3) | 2.671 (2) | 175 (3) |
N1A—H1A···O2Siii | 0.85 (3) | 2.00 (3) | 2.740 (2) | 146 (2) |
N2A—H2A···O1Wii | 0.88 (3) | 1.99 (3) | 2.855 (3) | 169 (2) |
O1W—H1WA···O4Siv | 0.85 (3) | 1.92 (4) | 2.752 (3) | 170 (3) |
O1W—H1WB···O3Wv | 0.88 (4) | 1.99 (4) | 2.831 (3) | 158 (3) |
O2W—H2WA···O1Avi | 1.04 (9) | 2.48 (9) | 3.262 (3) | 132 (6) |
O2W—H2WB···O4Svii | 0.96 (4) | 1.85 (4) | 2.806 (3) | 173 (3) |
O3W—H3WA···O2Sviii | 0.83 (4) | 2.03 (4) | 2.825 (2) | 158 (3) |
O3W—H3WB···O1Six | 0.88 (4) | 1.91 (4) | 2.763 (2) | 165 (3) |
O4W—H4WA···O2W | 0.81 (4) | 1.99 (4) | 2.793 (3) | 171 (4) |
O4W—H4WB···O3W | 0.91 (4) | 1.90 (4) | 2.805 (3) | 170 (3) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+1, −y+2, −z+2; (v) x, y+1, z; (vi) −x+1, −y, −z+1; (vii) x, y−1, z; (viii) −x+1, −y+1, −z+2; (ix) x−1, y−1, z. |
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It is well known that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with interesting biological activities. A large variety of quinoline derivatives have been used as antimalarial, anti-inflammatory agents, antiasthmatic, antibacterial, antihypertensive and tyrokinase PDGF-RTK inhibiting agents. Furthermore, poly-substituted quinolines have been found to undergo hierarchical self-assembly into a variety of nano- and mesostructures with enhanced electronic and photonic functions.
Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions. On the industrial scale, they have wide range of applications such as dyes and pigments.
The title compound, (I), a new Schiff base was synthesized and its crystal structure has been determined. The geometric parameters for (I) are in the usual ranges. There are two organic molecules in the asymmetric unit. The dihedral angles between the mean planes of their two aromatic ring systems are 10.94 (9)° and 7.14 (8)°, respectively. The crystal packing is stabilized by many N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1).