organic compounds
N-Butyl-4-butylimino-2-methylpentan-2-aminium (E)-quercetinate
aNational Institute for R&D of Isotopic and Molecular Technologies, PO Box 700, Cluj-Napoca R-400293, Romania
*Correspondence e-mail: mihaela.pop@itim-cj.ro
The title salt, C14H31N2+·C15H9O7−, was obtained in the reaction of quercetin with n-butylamine in a mixture of acetone and hexane. The determination shows that the quercetin donates one of its phenol H atoms to the N-butyl-4-butylimino-2-methylpentan-2-amine molecule. The of the salt is stabilized by intramolecular (N—H⋯N for the cation and O—H⋯O for the anion) and intermolecular hydrogen bonding (N—H⋯O between cation–anion pairs and O—H⋯O between anions). Quercetin molecules form dimers connected into a two-dimensional network. The dihedral angle between the quercetin ring systems is 19.61 (8)°.
Related literature
For the antioxidant activity of quercetin, see: Young et al. (1999). For related structures, see: Clarke et al. (2010); Kavuru et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Supporting information
https://doi.org/10.1107/S1600536812031170/kj2204sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031170/kj2204Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812031170/kj2204Isup3.cml
The title compound (C15H9O7) (C14H31N2) was obtained in the reaction of quercetin with n-butylamine in a mixture of acetone/hexane. A suspension of quercetin dihydrate (0.044 mmol) in a mixture of acetone (2 ml) and hexane (1 ml) was stirred at 333 K for 30 minutes. The suspension was filtered and the clear solution was placed in a vial. The vial containing the quercetin solution was placed in a larger vial containing n-butylamine (2.5 ml). The vial was sealed to allow the slow diffusion of the amine vapors into the acetone/hexane quercetin solution. Yellow crystals of (I) were obtained after three days.
All H atoms were located in a difference map. The hydrogen atoms of the methyl and hydroxyl groups were allowed to rotate to best fit the experimental electron density, whilst keeping fixed angles and distances (d(C-H) = 0.96 Å, d(O-H) = 0.82 Å), with U(H) set to 1.5 Ueq (C,O). The remaining H atoms were placed in the calculated positions with d(C-H) = 0.97 Å (CH2 groups), d(C-H) = 0.93 Å (aromatic ring) and d(N-H) = 0.9 Å. They were included in the
in the riding model approximation, with U(H) set to 1.2 Ueq (C,N).Quercetin belongs to the class of
which are naturally existing polyphenols possessing anti-oxidant activity (Young et al., 1999). forms of quercetin with theobromine and isonicotinic acid were reported (Clarke et al., 2010 and Kavuru et al., 2010). We present here the of the title compound (Fig. 1). Quercetin molecules form nearly planar dimers through hydroxyl-hydroxyl (O4A—H4A···O2Aii, Table 1) supra-molecular homosynthon. The dihedral angle between the quercetin ring systems is 19.61 (8) degrees. The quercetin dimers are further connected via OH···O intermolecular hydrogen bonding involving the phenyl moieties into an infinite two-dimensional network (base vectors [1 0 - 1], [0 - 1 0]), extending parallel to (1 0 1) as shown in Fig. 2. One phenolic OH of quercetin is engaged in hydrogen bonding with one molecule of N-butyl-4-(butylimino)-2-methylpentane-2-amine and it transfers the proton to the basic moiety. Therefore, the title compound is a salt and not a as the ones reported for quercetin so far.For the antioxidant activity of quercetin, see: Young et al. (1999). For related
structures, see: Clarke et al. (2010); Kavuru et al. (2010).Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C14H31N2+·C15H9O7− | F(000) = 1136 |
Mr = 528.63 | Dx = 1.258 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
a = 11.4017 (7) Å | Cell parameters from 9486 reflections |
b = 13.1730 (5) Å | θ = 3.1–28.9° |
c = 19.1961 (9) Å | µ = 0.09 mm−1 |
β = 104.438 (6)° | T = 293 K |
V = 2792.1 (2) Å3 | Prism, yellow |
Z = 4 | 0.3 × 0.2 × 0.1 mm |
SuperNova, Dual, Cu at zero, Eos diffractometer | 6574 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 4881 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 29.0°, θmin = 3.1° |
ω scans | h = −14→15 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010). | k = −16→17 |
Tmin = 0.647, Tmax = 1.000 | l = −24→26 |
25155 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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.233 | H-atom parameters constrained |
S = 1.57 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
6574 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C14H31N2+·C15H9O7− | V = 2792.1 (2) Å3 |
Mr = 528.63 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.4017 (7) Å | µ = 0.09 mm−1 |
b = 13.1730 (5) Å | T = 293 K |
c = 19.1961 (9) Å | 0.3 × 0.2 × 0.1 mm |
β = 104.438 (6)° |
SuperNova, Dual, Cu at zero, Eos diffractometer | 6574 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010). | 4881 reflections with I > 2σ(I) |
Tmin = 0.647, Tmax = 1.000 | Rint = 0.030 |
25155 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.233 | H-atom parameters constrained |
S = 1.57 | Δρmax = 0.41 e Å−3 |
6574 reflections | Δρmin = −0.38 e Å−3 |
352 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 | ||
O3A | 0.72169 (12) | 0.32311 (9) | 0.12724 (7) | 0.0363 (3) | |
O6A | 0.46443 (12) | 0.32713 (10) | 0.28345 (7) | 0.0406 (3) | |
C12A | 0.59541 (17) | 0.32353 (14) | 0.20600 (9) | 0.0348 (4) | |
H12A | 0.5636 | 0.2617 | 0.1867 | 0.042* | |
O4A | 0.94607 (14) | 0.49703 (10) | 0.09262 (8) | 0.0487 (4) | |
H4A | 0.9538 | 0.5572 | 0.1038 | 0.073* | |
C7A | 0.80878 (16) | 0.36415 (13) | 0.09754 (9) | 0.0331 (4) | |
C5A | 0.83343 (17) | 0.29650 (12) | 0.04206 (9) | 0.0325 (4) | |
O5A | 0.87994 (14) | 0.59111 (10) | 0.20140 (8) | 0.0507 (4) | |
O2A | 0.96400 (16) | 0.30683 (10) | −0.11267 (8) | 0.0557 (5) | |
H2A | 0.9692 | 0.2635 | −0.1424 | 0.084* | |
C10A | 0.73580 (17) | 0.46380 (13) | 0.20802 (9) | 0.0351 (4) | |
O7A | 0.73998 (17) | 0.59868 (12) | 0.29219 (9) | 0.0643 (5) | |
H7A | 0.7868 | 0.6201 | 0.2694 | 0.097* | |
C11A | 0.68442 (16) | 0.37099 (13) | 0.18113 (9) | 0.0321 (4) | |
C9A | 0.82744 (17) | 0.50911 (13) | 0.17907 (10) | 0.0365 (4) | |
C14A | 0.60419 (19) | 0.46257 (15) | 0.28970 (10) | 0.0423 (5) | |
H14A | 0.5774 | 0.4929 | 0.3267 | 0.051* | |
C8A | 0.85987 (17) | 0.45473 (13) | 0.12110 (10) | 0.0348 (4) | |
C6A | 0.89019 (16) | 0.33040 (13) | −0.01056 (9) | 0.0332 (4) | |
H6A | 0.9152 | 0.3977 | −0.0100 | 0.040* | |
C13A | 0.55355 (17) | 0.36998 (14) | 0.26088 (9) | 0.0352 (4) | |
C1A | 0.90966 (17) | 0.26601 (13) | −0.06322 (9) | 0.0347 (4) | |
C2A | 0.87269 (19) | 0.16429 (14) | −0.06480 (10) | 0.0407 (5) | |
C4A | 0.79879 (19) | 0.19478 (14) | 0.04075 (11) | 0.0411 (5) | |
H4AA | 0.7619 | 0.1701 | 0.0754 | 0.049* | |
C15A | 0.69287 (19) | 0.50915 (15) | 0.26400 (10) | 0.0421 (5) | |
C3A | 0.8190 (2) | 0.13110 (14) | −0.01161 (11) | 0.0454 (5) | |
H3A | 0.7960 | 0.0634 | −0.0114 | 0.054* | |
N2B | 0.27813 (17) | 0.27896 (12) | 0.16548 (11) | 0.0500 (5) | |
H2BA | 0.3331 | 0.2946 | 0.2065 | 0.060* | |
H2BB | 0.3193 | 0.2632 | 0.1326 | 0.060* | |
N1B | 0.39679 (19) | 0.13238 (17) | 0.10738 (12) | 0.0644 (6) | |
C8B | 0.2110 (2) | 0.18603 (17) | 0.17890 (15) | 0.0600 (6) | |
C12B | 0.2816 (3) | 0.46167 (19) | 0.13476 (16) | 0.0687 (7) | |
H12B | 0.2315 | 0.5220 | 0.1301 | 0.082* | |
H12C | 0.3435 | 0.4675 | 0.1796 | 0.082* | |
C7B | 0.3047 (2) | 0.10201 (17) | 0.20315 (14) | 0.0590 (6) | |
H7BA | 0.3593 | 0.1235 | 0.2480 | 0.071* | |
H7BB | 0.2624 | 0.0423 | 0.2137 | 0.071* | |
C5B | 0.3785 (2) | 0.07113 (18) | 0.15472 (14) | 0.0602 (6) | |
C3B | 0.4607 (3) | 0.1825 (3) | −0.00001 (18) | 0.0922 (10) | |
H3BA | 0.5218 | 0.1684 | −0.0260 | 0.111* | |
H3BB | 0.4758 | 0.2498 | 0.0207 | 0.111* | |
C9B | 0.1187 (2) | 0.1555 (2) | 0.11018 (18) | 0.0795 (9) | |
H9BA | 0.0567 | 0.2065 | 0.0981 | 0.119* | |
H9BB | 0.0829 | 0.0917 | 0.1174 | 0.119* | |
H9BC | 0.1583 | 0.1492 | 0.0717 | 0.119* | |
C13B | 0.3421 (3) | 0.4609 (3) | 0.0749 (2) | 0.0939 (10) | |
H13A | 0.2810 | 0.4594 | 0.0295 | 0.113* | |
H13B | 0.3906 | 0.3998 | 0.0779 | 0.113* | |
C6B | 0.4337 (3) | −0.0340 (2) | 0.16675 (19) | 0.0844 (9) | |
H6BA | 0.3785 | −0.0825 | 0.1389 | 0.127* | |
H6BB | 0.4492 | −0.0512 | 0.2168 | 0.127* | |
H6BC | 0.5083 | −0.0351 | 0.1522 | 0.127* | |
C11B | 0.2045 (3) | 0.37186 (18) | 0.14017 (18) | 0.0738 (8) | |
H11A | 0.1504 | 0.3585 | 0.0934 | 0.089* | |
H11B | 0.1551 | 0.3872 | 0.1733 | 0.089* | |
C10B | 0.1493 (3) | 0.2091 (2) | 0.2401 (2) | 0.0884 (10) | |
H10A | 0.2089 | 0.2323 | 0.2817 | 0.133* | |
H10B | 0.1115 | 0.1486 | 0.2519 | 0.133* | |
H10C | 0.0891 | 0.2609 | 0.2247 | 0.133* | |
C4B | 0.4711 (3) | 0.1058 (3) | 0.05941 (18) | 0.0874 (9) | |
H4BA | 0.4468 | 0.0396 | 0.0385 | 0.105* | |
H4BB | 0.5549 | 0.1012 | 0.0866 | 0.105* | |
C14B | 0.4228 (4) | 0.5531 (3) | 0.0763 (3) | 0.1369 (19) | |
H14B | 0.3809 | 0.6130 | 0.0854 | 0.205* | |
H14C | 0.4425 | 0.5596 | 0.0307 | 0.205* | |
H14D | 0.4958 | 0.5450 | 0.1136 | 0.205* | |
C1B | 0.3270 (6) | 0.2454 (5) | −0.1144 (3) | 0.175 (3) | |
H1BA | 0.3371 | 0.3149 | −0.0990 | 0.263* | |
H1BB | 0.2487 | 0.2368 | −0.1469 | 0.263* | |
H1BC | 0.3887 | 0.2276 | −0.1383 | 0.263* | |
C2B | 0.3368 (4) | 0.1799 (4) | −0.0518 (3) | 0.1251 (14) | |
H2BC | 0.3185 | 0.1106 | −0.0682 | 0.150* | |
H2BD | 0.2769 | 0.2007 | −0.0266 | 0.150* | |
O1A | 0.88657 (18) | 0.09668 (11) | −0.11484 (9) | 0.0658 (5) | |
H1A | 0.9087 | 0.1263 | −0.1469 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3A | 0.0456 (8) | 0.0369 (7) | 0.0352 (7) | −0.0082 (5) | 0.0265 (6) | −0.0079 (5) |
O6A | 0.0461 (8) | 0.0475 (7) | 0.0370 (7) | −0.0029 (6) | 0.0267 (6) | 0.0032 (5) |
C12A | 0.0403 (11) | 0.0365 (9) | 0.0325 (9) | −0.0025 (7) | 0.0181 (8) | −0.0008 (7) |
O4A | 0.0599 (10) | 0.0430 (8) | 0.0573 (9) | −0.0183 (6) | 0.0415 (8) | −0.0152 (6) |
C7A | 0.0378 (10) | 0.0378 (9) | 0.0294 (8) | −0.0020 (7) | 0.0192 (7) | −0.0010 (7) |
C5A | 0.0363 (10) | 0.0352 (9) | 0.0305 (8) | −0.0023 (7) | 0.0171 (7) | −0.0029 (7) |
O5A | 0.0632 (10) | 0.0441 (8) | 0.0543 (9) | −0.0195 (7) | 0.0325 (7) | −0.0165 (6) |
O2A | 0.0947 (12) | 0.0401 (7) | 0.0511 (9) | −0.0205 (7) | 0.0534 (9) | −0.0132 (6) |
C10A | 0.0397 (11) | 0.0392 (9) | 0.0309 (9) | −0.0024 (7) | 0.0172 (7) | −0.0040 (7) |
O7A | 0.0866 (13) | 0.0574 (9) | 0.0655 (10) | −0.0290 (8) | 0.0499 (9) | −0.0337 (8) |
C11A | 0.0389 (10) | 0.0346 (9) | 0.0272 (8) | 0.0015 (7) | 0.0163 (7) | −0.0011 (6) |
C9A | 0.0418 (11) | 0.0376 (9) | 0.0339 (9) | −0.0057 (7) | 0.0167 (8) | −0.0051 (7) |
C14A | 0.0524 (13) | 0.0477 (10) | 0.0352 (9) | −0.0020 (9) | 0.0265 (9) | −0.0090 (8) |
C8A | 0.0381 (10) | 0.0372 (9) | 0.0350 (9) | −0.0030 (7) | 0.0204 (8) | −0.0028 (7) |
C6A | 0.0420 (11) | 0.0308 (8) | 0.0319 (9) | −0.0040 (7) | 0.0184 (7) | −0.0021 (7) |
C13A | 0.0403 (11) | 0.0421 (9) | 0.0286 (8) | 0.0024 (8) | 0.0186 (7) | 0.0049 (7) |
C1A | 0.0433 (11) | 0.0345 (8) | 0.0329 (9) | −0.0043 (7) | 0.0220 (8) | −0.0007 (7) |
C2A | 0.0545 (13) | 0.0367 (9) | 0.0389 (10) | −0.0092 (8) | 0.0265 (9) | −0.0097 (7) |
C4A | 0.0515 (12) | 0.0404 (9) | 0.0404 (10) | −0.0108 (8) | 0.0283 (9) | −0.0051 (8) |
C15A | 0.0517 (13) | 0.0438 (10) | 0.0369 (9) | −0.0076 (8) | 0.0223 (9) | −0.0103 (8) |
C3A | 0.0644 (14) | 0.0340 (9) | 0.0480 (11) | −0.0142 (8) | 0.0335 (10) | −0.0080 (8) |
N2B | 0.0492 (11) | 0.0421 (9) | 0.0576 (11) | 0.0029 (7) | 0.0115 (8) | 0.0013 (8) |
N1B | 0.0646 (14) | 0.0664 (13) | 0.0640 (13) | 0.0019 (10) | 0.0192 (11) | −0.0097 (11) |
C8B | 0.0535 (15) | 0.0461 (12) | 0.0791 (17) | −0.0036 (10) | 0.0140 (12) | 0.0046 (11) |
C12B | 0.0732 (18) | 0.0513 (13) | 0.0774 (18) | 0.0080 (12) | 0.0106 (14) | 0.0126 (12) |
C7B | 0.0611 (16) | 0.0458 (12) | 0.0670 (15) | −0.0023 (10) | 0.0103 (12) | 0.0027 (10) |
C5B | 0.0614 (16) | 0.0512 (13) | 0.0614 (15) | −0.0032 (10) | 0.0031 (12) | −0.0038 (11) |
C3B | 0.088 (2) | 0.121 (3) | 0.0681 (19) | 0.0099 (19) | 0.0205 (17) | −0.0051 (18) |
C9B | 0.0555 (17) | 0.0577 (14) | 0.111 (2) | −0.0062 (12) | −0.0055 (15) | −0.0007 (15) |
C13B | 0.103 (2) | 0.093 (2) | 0.089 (2) | 0.0237 (19) | 0.0301 (19) | 0.0281 (18) |
C6B | 0.093 (2) | 0.0599 (16) | 0.093 (2) | 0.0146 (15) | 0.0105 (17) | −0.0055 (15) |
C11B | 0.0647 (17) | 0.0482 (13) | 0.104 (2) | 0.0104 (11) | 0.0132 (15) | 0.0108 (13) |
C10B | 0.093 (2) | 0.0713 (18) | 0.118 (3) | 0.0025 (16) | 0.059 (2) | 0.0081 (18) |
C4B | 0.093 (2) | 0.097 (2) | 0.0758 (19) | 0.0072 (18) | 0.0288 (17) | −0.0140 (17) |
C14B | 0.108 (3) | 0.126 (3) | 0.183 (5) | −0.001 (2) | 0.046 (3) | 0.079 (3) |
C1B | 0.190 (6) | 0.140 (4) | 0.143 (5) | −0.015 (4) | −0.059 (4) | 0.032 (4) |
C2B | 0.123 (3) | 0.143 (4) | 0.101 (3) | −0.001 (3) | 0.014 (3) | 0.024 (3) |
O1A | 0.1151 (15) | 0.0414 (8) | 0.0631 (10) | −0.0239 (8) | 0.0637 (11) | −0.0208 (7) |
O3A—C7A | 1.373 (2) | C8B—C10B | 1.542 (4) |
O3A—C11A | 1.3667 (19) | C12B—H12B | 0.9700 |
O6A—C13A | 1.326 (2) | C12B—H12C | 0.9700 |
C12A—H12A | 0.9300 | C12B—C13B | 1.481 (4) |
C12A—C11A | 1.375 (2) | C12B—C11B | 1.493 (4) |
C12A—C13A | 1.401 (2) | C7B—H7BA | 0.9700 |
O4A—H4A | 0.8200 | C7B—H7BB | 0.9700 |
O4A—C8A | 1.358 (2) | C7B—C5B | 1.458 (4) |
C7A—C5A | 1.468 (2) | C5B—C6B | 1.515 (4) |
C7A—C8A | 1.355 (2) | C3B—H3BA | 0.9700 |
C5A—C6A | 1.402 (2) | C3B—H3BB | 0.9700 |
C5A—C4A | 1.395 (2) | C3B—C4B | 1.506 (5) |
O5A—C9A | 1.257 (2) | C3B—C2B | 1.512 (6) |
O2A—H2A | 0.8200 | C9B—H9BA | 0.9600 |
O2A—C1A | 1.366 (2) | C9B—H9BB | 0.9600 |
C10A—C11A | 1.398 (2) | C9B—H9BC | 0.9600 |
C10A—C9A | 1.430 (2) | C13B—H13A | 0.9700 |
C10A—C15A | 1.419 (2) | C13B—H13B | 0.9700 |
O7A—H7A | 0.8200 | C13B—C14B | 1.520 (5) |
O7A—C15A | 1.352 (2) | C6B—H6BA | 0.9600 |
C9A—C8A | 1.447 (2) | C6B—H6BB | 0.9600 |
C14A—H14A | 0.9300 | C6B—H6BC | 0.9600 |
C14A—C13A | 1.403 (3) | C11B—H11A | 0.9700 |
C14A—C15A | 1.375 (3) | C11B—H11B | 0.9700 |
C6A—H6A | 0.9300 | C10B—H10A | 0.9600 |
C6A—C1A | 1.379 (2) | C10B—H10B | 0.9600 |
C1A—C2A | 1.403 (2) | C10B—H10C | 0.9600 |
C2A—C3A | 1.385 (2) | C4B—H4BA | 0.9700 |
C2A—O1A | 1.348 (2) | C4B—H4BB | 0.9700 |
C4A—H4AA | 0.9300 | C14B—H14B | 0.9600 |
C4A—C3A | 1.372 (3) | C14B—H14C | 0.9600 |
C3A—H3A | 0.9300 | C14B—H14D | 0.9600 |
N2B—H2BA | 0.9000 | C1B—H1BA | 0.9600 |
N2B—H2BB | 0.9000 | C1B—H1BB | 0.9600 |
N2B—C8B | 1.500 (3) | C1B—H1BC | 0.9600 |
N2B—C11B | 1.495 (3) | C1B—C2B | 1.460 (7) |
N1B—C5B | 1.271 (3) | C2B—H2BC | 0.9700 |
N1B—C4B | 1.441 (4) | C2B—H2BD | 0.9700 |
C8B—C7B | 1.528 (3) | O1A—H1A | 0.8200 |
C8B—C9B | 1.522 (4) | ||
C11A—O3A—C7A | 121.74 (13) | C8B—C7B—H7BB | 107.7 |
C11A—C12A—H12A | 120.6 | H7BA—C7B—H7BB | 107.1 |
C11A—C12A—C13A | 118.81 (16) | C5B—C7B—C8B | 118.6 (2) |
C13A—C12A—H12A | 120.6 | C5B—C7B—H7BA | 107.7 |
C8A—O4A—H4A | 109.5 | C5B—C7B—H7BB | 107.7 |
O3A—C7A—C5A | 110.56 (14) | N1B—C5B—C7B | 120.2 (2) |
C8A—C7A—O3A | 120.22 (15) | N1B—C5B—C6B | 123.6 (3) |
C8A—C7A—C5A | 129.22 (15) | C7B—C5B—C6B | 116.2 (2) |
C6A—C5A—C7A | 122.38 (15) | H3BA—C3B—H3BB | 108.0 |
C4A—C5A—C7A | 119.43 (15) | C4B—C3B—H3BA | 109.3 |
C4A—C5A—C6A | 118.19 (15) | C4B—C3B—H3BB | 109.3 |
C1A—O2A—H2A | 109.5 | C4B—C3B—C2B | 111.5 (3) |
C11A—C10A—C9A | 120.06 (15) | C2B—C3B—H3BA | 109.3 |
C11A—C10A—C15A | 117.13 (16) | C2B—C3B—H3BB | 109.3 |
C15A—C10A—C9A | 122.81 (16) | C8B—C9B—H9BA | 109.5 |
C15A—O7A—H7A | 109.5 | C8B—C9B—H9BB | 109.5 |
O3A—C11A—C12A | 116.66 (15) | C8B—C9B—H9BC | 109.5 |
O3A—C11A—C10A | 120.16 (15) | H9BA—C9B—H9BB | 109.5 |
C12A—C11A—C10A | 123.18 (15) | H9BA—C9B—H9BC | 109.5 |
O5A—C9A—C10A | 123.90 (16) | H9BB—C9B—H9BC | 109.5 |
O5A—C9A—C8A | 119.76 (16) | C12B—C13B—H13A | 109.2 |
C10A—C9A—C8A | 116.34 (15) | C12B—C13B—H13B | 109.2 |
C13A—C14A—H14A | 119.5 | C12B—C13B—C14B | 112.2 (4) |
C15A—C14A—H14A | 119.5 | H13A—C13B—H13B | 107.9 |
C15A—C14A—C13A | 120.90 (16) | C14B—C13B—H13A | 109.2 |
O4A—C8A—C9A | 117.12 (15) | C14B—C13B—H13B | 109.2 |
C7A—C8A—O4A | 121.41 (15) | C5B—C6B—H6BA | 109.5 |
C7A—C8A—C9A | 121.44 (16) | C5B—C6B—H6BB | 109.5 |
C5A—C6A—H6A | 119.3 | C5B—C6B—H6BC | 109.5 |
C1A—C6A—C5A | 121.33 (15) | H6BA—C6B—H6BB | 109.5 |
C1A—C6A—H6A | 119.3 | H6BA—C6B—H6BC | 109.5 |
O6A—C13A—C12A | 119.50 (17) | H6BB—C6B—H6BC | 109.5 |
O6A—C13A—C14A | 120.98 (15) | N2B—C11B—H11A | 109.2 |
C12A—C13A—C14A | 119.50 (16) | N2B—C11B—H11B | 109.2 |
O2A—C1A—C6A | 116.80 (15) | C12B—C11B—N2B | 112.2 (2) |
O2A—C1A—C2A | 123.14 (15) | C12B—C11B—H11A | 109.2 |
C6A—C1A—C2A | 120.06 (15) | C12B—C11B—H11B | 109.2 |
C3A—C2A—C1A | 118.10 (16) | H11A—C11B—H11B | 107.9 |
O1A—C2A—C1A | 123.96 (16) | C8B—C10B—H10A | 109.5 |
O1A—C2A—C3A | 117.94 (16) | C8B—C10B—H10B | 109.5 |
C5A—C4A—H4AA | 119.9 | C8B—C10B—H10C | 109.5 |
C3A—C4A—C5A | 120.12 (16) | H10A—C10B—H10B | 109.5 |
C3A—C4A—H4AA | 119.9 | H10A—C10B—H10C | 109.5 |
O7A—C15A—C10A | 119.52 (17) | H10B—C10B—H10C | 109.5 |
O7A—C15A—C14A | 120.01 (16) | N1B—C4B—C3B | 111.9 (3) |
C14A—C15A—C10A | 120.47 (17) | N1B—C4B—H4BA | 109.2 |
C2A—C3A—H3A | 118.9 | N1B—C4B—H4BB | 109.2 |
C4A—C3A—C2A | 122.19 (17) | C3B—C4B—H4BA | 109.2 |
C4A—C3A—H3A | 118.9 | C3B—C4B—H4BB | 109.2 |
H2BA—N2B—H2BB | 107.3 | H4BA—C4B—H4BB | 107.9 |
C8B—N2B—H2BA | 108.0 | C13B—C14B—H14B | 109.5 |
C8B—N2B—H2BB | 108.0 | C13B—C14B—H14C | 109.5 |
C11B—N2B—H2BA | 108.0 | C13B—C14B—H14D | 109.5 |
C11B—N2B—H2BB | 108.0 | H14B—C14B—H14C | 109.5 |
C11B—N2B—C8B | 117.04 (19) | H14B—C14B—H14D | 109.5 |
C5B—N1B—C4B | 122.0 (2) | H14C—C14B—H14D | 109.5 |
N2B—C8B—C7B | 107.19 (19) | H1BA—C1B—H1BB | 109.5 |
N2B—C8B—C9B | 109.8 (2) | H1BA—C1B—H1BC | 109.5 |
N2B—C8B—C10B | 108.6 (2) | H1BB—C1B—H1BC | 109.5 |
C7B—C8B—C10B | 109.1 (2) | C2B—C1B—H1BA | 109.5 |
C9B—C8B—C7B | 110.7 (2) | C2B—C1B—H1BB | 109.5 |
C9B—C8B—C10B | 111.3 (2) | C2B—C1B—H1BC | 109.5 |
H12B—C12B—H12C | 107.3 | C3B—C2B—H2BC | 108.9 |
C13B—C12B—H12B | 108.2 | C3B—C2B—H2BD | 108.9 |
C13B—C12B—H12C | 108.2 | C1B—C2B—C3B | 113.3 (4) |
C13B—C12B—C11B | 116.4 (3) | C1B—C2B—H2BC | 108.9 |
C11B—C12B—H12B | 108.2 | C1B—C2B—H2BD | 108.9 |
C11B—C12B—H12C | 108.2 | H2BC—C2B—H2BD | 107.7 |
C8B—C7B—H7BA | 107.7 | C2A—O1A—H1A | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2B—H2BA···O6A | 0.9 | 1.87 | 2.765 (2) | 171 |
N2B—H2BB···N1B | 0.9 | 2.05 | 2.749 (3) | 134 |
O7A—H7A···O5A | 0.82 | 1.92 | 2.642 (2) | 147 |
O1A—H1A···O6Ai | 0.82 | 1.73 | 2.544 (2) | 172 |
O2A—H2A···O6Ai | 0.82 | 1.85 | 2.6637 (19) | 173 |
O4A—H4A···O2Aii | 0.82 | 2.01 | 2.771 (2) | 154 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H31N2+·C15H9O7− |
Mr | 528.63 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.4017 (7), 13.1730 (5), 19.1961 (9) |
β (°) | 104.438 (6) |
V (Å3) | 2792.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 |
Data collection | |
Diffractometer | SuperNova, Dual, Cu at zero, Eos |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010). |
Tmin, Tmax | 0.647, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25155, 6574, 4881 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.233, 1.57 |
No. of reflections | 6574 |
No. of parameters | 352 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.38 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2B—H2BA···O6A | 0.9 | 1.87 | 2.765 (2) | 171 |
N2B—H2BB···N1B | 0.9 | 2.05 | 2.749 (3) | 134 |
O7A—H7A···O5A | 0.82 | 1.92 | 2.642 (2) | 147 |
O1A—H1A···O6Ai | 0.82 | 1.73 | 2.544 (2) | 172 |
O2A—H2A···O6Ai | 0.82 | 1.85 | 2.6637 (19) | 173 |
O4A—H4A···O2Aii | 0.82 | 2.01 | 2.771 (2) | 154 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z. |
Acknowledgements
This work was supported by ANCS, project No. POSCCE ID536.
References
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Quercetin belongs to the class of flavonoids which are naturally existing polyphenols possessing anti-oxidant activity (Young et al., 1999). Co-crystal forms of quercetin with theobromine and isonicotinic acid were reported (Clarke et al., 2010 and Kavuru et al., 2010). We present here the crystal structure of the title compound (Fig. 1). Quercetin molecules form nearly planar dimers through hydroxyl-hydroxyl (O4A—H4A···O2Aii, Table 1) supra-molecular homosynthon. The dihedral angle between the quercetin ring systems is 19.61 (8) degrees. The quercetin dimers are further connected via OH···O intermolecular hydrogen bonding involving the phenyl moieties into an infinite two-dimensional network (base vectors [1 0 - 1], [0 - 1 0]), extending parallel to (1 0 1) as shown in Fig. 2. One phenolic OH of quercetin is engaged in hydrogen bonding with one molecule of N-butyl-4-(butylimino)-2-methylpentane-2-amine and it transfers the proton to the basic moiety. Therefore, the title compound is a salt and not a co-crystal as the ones reported for quercetin so far.