The title compound (alternative names 7,8-dimethoxydictammine and 4,7,8-trimethoxyfuro[2,3-
b]quinoline), C
14H
13NO
4, is a natural product extracted from
Adiscanthus fusciflorus (
Rutaceae). Our biochemical tests show that it has inhibitory activity against the enzyme adenine phosphoribosyltransferase (APRT) from Leishmania, a tropical parasite causing endemic disease in poor countries. It crystallizes in the centrosymmetric space group
P2
1/
c, with one molecule in the asymmetric unit, and has at least two C—H
O intermolecular interactions, leading to the formation of centrosymmetric dimers.
Supporting information
CCDC reference: 225768
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.104
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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) and PLATON (Spek, 2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Crystal data top
C14H13NO4 | F(000) = 544 |
Mr = 259.25 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2808 reflections |
a = 7.2429 (1) Å | θ = 3.4–27.5° |
b = 10.4418 (2) Å | µ = 0.11 mm−1 |
c = 15.4618 (3) Å | T = 120 K |
β = 94.353 (1)° | Prism, light yellow |
V = 1165.99 (4) Å3 | 0.32 × 0.18 × 0.16 mm |
Z = 4 | |
Data collection top
KappaCCD diffractometer | Rint = 0.013 |
φ and ω scans | θmax = 27.5°, θmin = 3.8° |
5117 measured reflections | h = −9→9 |
2672 independent reflections | k = −13→13 |
2301 reflections with I > 2σ(I) | l = −20→20 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2061P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.29 e Å−3 |
2672 reflections | Δρmin = −0.22 e Å−3 |
207 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | 0.33424 (12) | 0.57374 (9) | 0.13399 (5) | 0.0194 (2) | |
O1 | 0.42550 (11) | 0.43483 (8) | 0.24532 (5) | 0.0243 (2) | |
O2 | 0.28060 (11) | 0.25320 (7) | −0.03212 (5) | 0.0233 (2) | |
O3 | 0.27979 (10) | 0.81129 (7) | 0.06424 (5) | 0.02058 (19) | |
O4 | 0.13823 (11) | 0.84432 (7) | −0.09956 (5) | 0.0245 (2) | |
C1 | 0.36749 (14) | 0.45696 (11) | 0.15976 (6) | 0.0194 (2) | |
C2 | 0.35529 (13) | 0.33930 (10) | 0.11348 (7) | 0.0192 (2) | |
C3 | 0.29818 (13) | 0.34916 (10) | 0.02597 (7) | 0.0186 (2) | |
C4 | 0.25319 (13) | 0.47355 (10) | −0.00799 (6) | 0.0177 (2) | |
C5 | 0.27531 (13) | 0.58198 (10) | 0.04770 (6) | 0.0175 (2) | |
C6 | 0.18805 (14) | 0.49268 (11) | −0.09582 (7) | 0.0200 (2) | |
C7 | 0.14623 (14) | 0.61268 (11) | −0.12728 (7) | 0.0208 (2) | |
C8 | 0.17206 (14) | 0.72110 (10) | −0.07294 (6) | 0.0186 (2) | |
C9 | 0.23761 (13) | 0.70556 (10) | 0.01291 (7) | 0.0178 (2) | |
C10 | 0.45022 (15) | 0.30320 (11) | 0.25283 (8) | 0.0253 (3) | |
C11 | 0.41129 (14) | 0.24193 (11) | 0.17749 (7) | 0.0234 (2) | |
C12 | 0.32400 (16) | 0.12536 (11) | −0.00303 (8) | 0.0261 (3) | |
C13 | 0.13052 (15) | 0.85758 (11) | 0.11072 (7) | 0.0249 (2) | |
H13A | 0.0434 | 0.9021 | 0.0716 | 0.037* | |
H13B | 0.1777 | 0.9151 | 0.1555 | 0.037* | |
H13C | 0.07 | 0.7867 | 0.1363 | 0.037* | |
C14 | 0.09275 (16) | 0.86442 (11) | −0.19021 (7) | 0.0244 (2) | |
H6 | 0.1727 (18) | 0.4202 (15) | −0.1341 (8) | 0.027 (3)* | |
H7 | 0.0956 (19) | 0.6262 (15) | −0.1894 (10) | 0.035 (4)* | |
H11 | 0.4213 (18) | 0.1499 (14) | 0.1694 (9) | 0.027 (3)* | |
H10 | 0.4961 (18) | 0.2723 (14) | 0.3098 (9) | 0.027 (3)* | |
H12A | 0.454 (2) | 0.1187 (15) | 0.0224 (10) | 0.041* | |
H12B | 0.307 (2) | 0.0721 (16) | −0.0552 (10) | 0.041* | |
H12C | 0.241 (2) | 0.0970 (16) | 0.0400 (10) | 0.041* | |
H14A | 0.189 (2) | 0.8265 (15) | −0.2252 (10) | 0.041* | |
H14B | 0.089 (2) | 0.9608 (17) | −0.1963 (9) | 0.041* | |
H14C | −0.032 (2) | 0.8273 (15) | −0.2072 (10) | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.0198 (4) | 0.0202 (4) | 0.0179 (4) | 0.0013 (3) | −0.0001 (3) | −0.0006 (3) |
O1 | 0.0288 (4) | 0.0239 (4) | 0.0194 (4) | 0.0034 (3) | −0.0040 (3) | 0.0025 (3) |
O2 | 0.0292 (4) | 0.0149 (4) | 0.0253 (4) | 0.0008 (3) | −0.0002 (3) | −0.0024 (3) |
O3 | 0.0217 (4) | 0.0172 (4) | 0.0228 (4) | −0.0003 (3) | 0.0019 (3) | −0.0052 (3) |
O4 | 0.0351 (4) | 0.0183 (4) | 0.0198 (4) | 0.0040 (3) | −0.0003 (3) | 0.0022 (3) |
C1 | 0.0175 (5) | 0.0227 (5) | 0.0178 (5) | 0.0017 (4) | −0.0002 (4) | 0.0017 (4) |
C2 | 0.0155 (5) | 0.0196 (5) | 0.0225 (5) | 0.0002 (4) | 0.0017 (4) | 0.0013 (4) |
C3 | 0.0161 (4) | 0.0180 (5) | 0.0219 (5) | −0.0007 (4) | 0.0024 (4) | −0.0026 (4) |
C4 | 0.0157 (5) | 0.0182 (5) | 0.0195 (5) | −0.0007 (4) | 0.0026 (4) | −0.0012 (4) |
C5 | 0.0150 (4) | 0.0187 (5) | 0.0188 (5) | −0.0002 (4) | 0.0015 (4) | −0.0005 (4) |
C6 | 0.0207 (5) | 0.0205 (5) | 0.0188 (5) | −0.0009 (4) | 0.0012 (4) | −0.0031 (4) |
C7 | 0.0220 (5) | 0.0230 (5) | 0.0172 (5) | 0.0001 (4) | 0.0006 (4) | −0.0010 (4) |
C8 | 0.0191 (5) | 0.0174 (5) | 0.0193 (5) | 0.0012 (4) | 0.0024 (4) | 0.0017 (4) |
C9 | 0.0174 (5) | 0.0171 (5) | 0.0191 (5) | −0.0004 (4) | 0.0016 (4) | −0.0022 (4) |
C10 | 0.0248 (5) | 0.0241 (6) | 0.0265 (6) | 0.0028 (4) | −0.0013 (4) | 0.0063 (4) |
C11 | 0.0214 (5) | 0.0220 (5) | 0.0267 (5) | 0.0018 (4) | 0.0002 (4) | 0.0051 (4) |
C12 | 0.0283 (6) | 0.0155 (5) | 0.0340 (6) | 0.0004 (4) | 0.0002 (5) | −0.0015 (4) |
C13 | 0.0270 (5) | 0.0240 (6) | 0.0240 (5) | 0.0017 (4) | 0.0043 (4) | −0.0052 (4) |
C14 | 0.0280 (6) | 0.0250 (6) | 0.0202 (5) | 0.0045 (4) | 0.0013 (4) | 0.0050 (4) |
Geometric parameters (Å, º) top
N—C1 | 1.2996 (14) | C6—C7 | 1.3697 (15) |
N—C5 | 1.3723 (13) | C6—H6 | 0.962 (15) |
O1—C1 | 1.3769 (12) | C7—C8 | 1.4137 (15) |
O1—C10 | 1.3898 (14) | C7—H7 | 1.012 (15) |
O2—C3 | 1.3452 (12) | C8—C9 | 1.3848 (14) |
O2—C12 | 1.4358 (13) | C10—C11 | 1.3401 (16) |
O3—C9 | 1.3804 (12) | C10—H10 | 0.973 (14) |
O3—C13 | 1.4272 (12) | C11—H11 | 0.973 (15) |
O4—C8 | 1.3674 (13) | C12—H12A | 0.992 (16) |
O4—C14 | 1.4306 (13) | C12—H12B | 0.980 (16) |
C1—C2 | 1.4211 (15) | C12—H12C | 0.976 (15) |
C2—C3 | 1.3883 (15) | C13—H13A | 0.96 |
C2—C11 | 1.4549 (14) | C13—H13B | 0.96 |
C3—C4 | 1.4293 (14) | C13—H13C | 0.96 |
C4—C6 | 1.4176 (14) | C14—H14A | 0.999 (16) |
C4—C5 | 1.4240 (14) | C14—H14B | 1.011 (17) |
C5—C9 | 1.4166 (14) | C14—H14C | 0.998 (16) |
| | | |
C1—N—C5 | 113.18 (9) | C9—C8—C7 | 119.74 (10) |
C1—O1—C10 | 105.92 (8) | O3—C9—C8 | 120.14 (9) |
C3—O2—C12 | 118.42 (8) | O3—C9—C5 | 118.84 (9) |
C9—O3—C13 | 114.67 (8) | C8—C9—C5 | 120.86 (10) |
C8—O4—C14 | 117.11 (8) | C11—C10—O1 | 112.47 (10) |
N—C1—O1 | 119.20 (10) | C11—C10—H10 | 131.6 (9) |
N—C1—C2 | 130.83 (10) | O1—C10—H10 | 115.9 (9) |
O1—C1—C2 | 109.97 (9) | C10—C11—C2 | 106.69 (10) |
C3—C2—C1 | 115.41 (10) | C10—C11—H11 | 124.8 (8) |
C3—C2—C11 | 139.63 (10) | C2—C11—H11 | 128.5 (8) |
C1—C2—C11 | 104.96 (9) | O2—C12—H12A | 111.6 (9) |
O2—C3—C2 | 126.98 (10) | O2—C12—H12B | 105.0 (9) |
O2—C3—C4 | 115.10 (9) | H12A—C12—H12B | 110.1 (12) |
C2—C3—C4 | 117.91 (9) | O2—C12—H12C | 111.3 (10) |
C6—C4—C5 | 118.76 (9) | H12A—C12—H12C | 108.8 (12) |
C6—C4—C3 | 122.00 (9) | H12B—C12—H12C | 110.1 (13) |
C5—C4—C3 | 119.23 (9) | O3—C13—H13A | 109.5 |
N—C5—C9 | 117.59 (9) | O3—C13—H13B | 109.5 |
N—C5—C4 | 123.40 (10) | H13A—C13—H13B | 109.5 |
C9—C5—C4 | 119.01 (9) | O3—C13—H13C | 109.5 |
C7—C6—C4 | 121.18 (10) | H13A—C13—H13C | 109.5 |
C7—C6—H6 | 119.3 (8) | H13B—C13—H13C | 109.5 |
C4—C6—H6 | 119.5 (8) | O4—C14—H14A | 110.7 (9) |
C6—C7—C8 | 120.38 (9) | O4—C14—H14B | 103.9 (8) |
C6—C7—H7 | 121.3 (9) | H14A—C14—H14B | 111.1 (12) |
C8—C7—H7 | 118.3 (9) | O4—C14—H14C | 109.7 (9) |
O4—C8—C9 | 116.07 (9) | H14A—C14—H14C | 111.1 (12) |
O4—C8—C7 | 124.19 (9) | H14B—C14—H14C | 110.1 (12) |
| | | |
C5—N—C1—O1 | −179.22 (8) | C6—C7—C8—O4 | 178.33 (9) |
C5—N—C1—C2 | 1.00 (16) | C6—C7—C8—C9 | −0.90 (15) |
C10—O1—C1—N | −179.69 (9) | C13—O3—C9—C8 | 91.14 (11) |
C10—O1—C1—C2 | 0.13 (11) | C13—O3—C9—C5 | −93.42 (11) |
N—C1—C2—C3 | −0.10 (17) | O4—C8—C9—O3 | −5.38 (14) |
O1—C1—C2—C3 | −179.89 (8) | C7—C8—C9—O3 | 173.90 (8) |
N—C1—C2—C11 | 179.60 (11) | O4—C8—C9—C5 | 179.27 (8) |
O1—C1—C2—C11 | −0.19 (11) | C7—C8—C9—C5 | −1.45 (15) |
C12—O2—C3—C2 | 0.09 (15) | N—C5—C9—O3 | 6.65 (14) |
C12—O2—C3—C4 | 179.76 (8) | C4—C5—C9—O3 | −172.47 (8) |
C1—C2—C3—O2 | 178.01 (9) | N—C5—C9—C8 | −177.94 (8) |
C11—C2—C3—O2 | −1.6 (2) | C4—C5—C9—C8 | 2.94 (15) |
C1—C2—C3—C4 | −1.65 (14) | C1—O1—C10—C11 | −0.02 (12) |
C11—C2—C3—C4 | 178.79 (11) | O1—C10—C11—C2 | −0.10 (12) |
O2—C3—C4—C6 | 2.33 (14) | C3—C2—C11—C10 | 179.76 (13) |
C2—C3—C4—C6 | −177.97 (9) | C1—C2—C11—C10 | 0.17 (11) |
O2—C3—C4—C5 | −177.27 (8) | N—O1—O2—O3 | 2.22 (3) |
C2—C3—C4—C5 | 2.43 (14) | O1—O2—O3—O4 | −173.67 (3) |
C1—N—C5—C9 | −179.19 (8) | O2—O3—O4—C1 | 4.96 (3) |
C1—N—C5—C4 | −0.11 (14) | O3—O4—C1—C2 | −172.58 (8) |
C6—C4—C5—N | 178.82 (9) | O4—C1—C2—C3 | 0.54 (10) |
C3—C4—C5—N | −1.57 (15) | C1—C2—C3—C4 | −1.65 (14) |
C6—C4—C5—C9 | −2.11 (14) | C2—C3—C4—C5 | 2.43 (14) |
C3—C4—C5—C9 | 177.50 (8) | C3—C4—C5—C6 | 179.61 (15) |
C5—C4—C6—C7 | −0.18 (15) | C4—C5—C6—C7 | 179.85 (13) |
C3—C4—C6—C7 | −179.77 (9) | C5—C6—C7—C8 | 1.61 (10) |
C4—C6—C7—C8 | 1.70 (16) | C6—C7—C8—C9 | −0.90 (15) |
C14—O4—C8—C9 | 172.41 (9) | C7—C8—C9—C10 | −1.95 (16) |
C14—O4—C8—C7 | −6.84 (14) | C8—C9—C10—C11 | 3.84 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O3i | 0.97 (1) | 2.47 (1) | 3.315 (1) | 144.8 (11) |
C12—H12A···O3ii | 0.99 (1) | 2.54 (1) | 3.159 (1) | 120.3 (11) |
C10—H10···Ni | 0.97 (1) | 2.53 (1) | 3.290 (1) | 134.9 (11) |
C14—H14A···Niii | 0.99 (1) | 2.69 (1) | 3.403 (1) | 128.0 (11) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+3/2, z−1/2. |