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The title compound (alternative names 7,8-di­methoxy­dictam­mine and 4,7,8-tri­methoxy­furo­[2,3-b]­quinoline), C14H13NO4, 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 P21/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019913/ac6054sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019913/ac6054Isup2.hkl
Contains datablock I

CCDC reference: 225768

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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

Computing details top

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).

(I) top
Crystal data top
C14H13NO4F(000) = 544
Mr = 259.25Dx = 1.477 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2808 reflections
a = 7.2429 (1) Åθ = 3.4–27.5°
b = 10.4418 (2) ŵ = 0.11 mm1
c = 15.4618 (3) ÅT = 120 K
β = 94.353 (1)°Prism, light yellow
V = 1165.99 (4) Å30.32 × 0.18 × 0.16 mm
Z = 4
Data collection top
KappaCCD
diffractometer
Rint = 0.013
φ and ω scansθmax = 27.5°, θmin = 3.8°
5117 measured reflectionsh = 99
2672 independent reflectionsk = 1313
2301 reflections with I > 2σ(I)l = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH 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 = 1.04Δρmax = 0.29 e Å3
2672 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N0.33424 (12)0.57374 (9)0.13399 (5)0.0194 (2)
O10.42550 (11)0.43483 (8)0.24532 (5)0.0243 (2)
O20.28060 (11)0.25320 (7)0.03212 (5)0.0233 (2)
O30.27979 (10)0.81129 (7)0.06424 (5)0.02058 (19)
O40.13823 (11)0.84432 (7)0.09956 (5)0.0245 (2)
C10.36749 (14)0.45696 (11)0.15976 (6)0.0194 (2)
C20.35529 (13)0.33930 (10)0.11348 (7)0.0192 (2)
C30.29818 (13)0.34916 (10)0.02597 (7)0.0186 (2)
C40.25319 (13)0.47355 (10)0.00799 (6)0.0177 (2)
C50.27531 (13)0.58198 (10)0.04770 (6)0.0175 (2)
C60.18805 (14)0.49268 (11)0.09582 (7)0.0200 (2)
C70.14623 (14)0.61268 (11)0.12728 (7)0.0208 (2)
C80.17206 (14)0.72110 (10)0.07294 (6)0.0186 (2)
C90.23761 (13)0.70556 (10)0.01291 (7)0.0178 (2)
C100.45022 (15)0.30320 (11)0.25283 (8)0.0253 (3)
C110.41129 (14)0.24193 (11)0.17749 (7)0.0234 (2)
C120.32400 (16)0.12536 (11)0.00303 (8)0.0261 (3)
C130.13052 (15)0.85758 (11)0.11072 (7)0.0249 (2)
H13A0.04340.90210.07160.037*
H13B0.17770.91510.15550.037*
H13C0.070.78670.13630.037*
C140.09275 (16)0.86442 (11)0.19021 (7)0.0244 (2)
H60.1727 (18)0.4202 (15)0.1341 (8)0.027 (3)*
H70.0956 (19)0.6262 (15)0.1894 (10)0.035 (4)*
H110.4213 (18)0.1499 (14)0.1694 (9)0.027 (3)*
H100.4961 (18)0.2723 (14)0.3098 (9)0.027 (3)*
H12A0.454 (2)0.1187 (15)0.0224 (10)0.041*
H12B0.307 (2)0.0721 (16)0.0552 (10)0.041*
H12C0.241 (2)0.0970 (16)0.0400 (10)0.041*
H14A0.189 (2)0.8265 (15)0.2252 (10)0.041*
H14B0.089 (2)0.9608 (17)0.1963 (9)0.041*
H14C0.032 (2)0.8273 (15)0.2072 (10)0.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0198 (4)0.0202 (4)0.0179 (4)0.0013 (3)0.0001 (3)0.0006 (3)
O10.0288 (4)0.0239 (4)0.0194 (4)0.0034 (3)0.0040 (3)0.0025 (3)
O20.0292 (4)0.0149 (4)0.0253 (4)0.0008 (3)0.0002 (3)0.0024 (3)
O30.0217 (4)0.0172 (4)0.0228 (4)0.0003 (3)0.0019 (3)0.0052 (3)
O40.0351 (4)0.0183 (4)0.0198 (4)0.0040 (3)0.0003 (3)0.0022 (3)
C10.0175 (5)0.0227 (5)0.0178 (5)0.0017 (4)0.0002 (4)0.0017 (4)
C20.0155 (5)0.0196 (5)0.0225 (5)0.0002 (4)0.0017 (4)0.0013 (4)
C30.0161 (4)0.0180 (5)0.0219 (5)0.0007 (4)0.0024 (4)0.0026 (4)
C40.0157 (5)0.0182 (5)0.0195 (5)0.0007 (4)0.0026 (4)0.0012 (4)
C50.0150 (4)0.0187 (5)0.0188 (5)0.0002 (4)0.0015 (4)0.0005 (4)
C60.0207 (5)0.0205 (5)0.0188 (5)0.0009 (4)0.0012 (4)0.0031 (4)
C70.0220 (5)0.0230 (5)0.0172 (5)0.0001 (4)0.0006 (4)0.0010 (4)
C80.0191 (5)0.0174 (5)0.0193 (5)0.0012 (4)0.0024 (4)0.0017 (4)
C90.0174 (5)0.0171 (5)0.0191 (5)0.0004 (4)0.0016 (4)0.0022 (4)
C100.0248 (5)0.0241 (6)0.0265 (6)0.0028 (4)0.0013 (4)0.0063 (4)
C110.0214 (5)0.0220 (5)0.0267 (5)0.0018 (4)0.0002 (4)0.0051 (4)
C120.0283 (6)0.0155 (5)0.0340 (6)0.0004 (4)0.0002 (5)0.0015 (4)
C130.0270 (5)0.0240 (6)0.0240 (5)0.0017 (4)0.0043 (4)0.0052 (4)
C140.0280 (6)0.0250 (6)0.0202 (5)0.0045 (4)0.0013 (4)0.0050 (4)
Geometric parameters (Å, º) top
N—C11.2996 (14)C6—C71.3697 (15)
N—C51.3723 (13)C6—H60.962 (15)
O1—C11.3769 (12)C7—C81.4137 (15)
O1—C101.3898 (14)C7—H71.012 (15)
O2—C31.3452 (12)C8—C91.3848 (14)
O2—C121.4358 (13)C10—C111.3401 (16)
O3—C91.3804 (12)C10—H100.973 (14)
O3—C131.4272 (12)C11—H110.973 (15)
O4—C81.3674 (13)C12—H12A0.992 (16)
O4—C141.4306 (13)C12—H12B0.980 (16)
C1—C21.4211 (15)C12—H12C0.976 (15)
C2—C31.3883 (15)C13—H13A0.96
C2—C111.4549 (14)C13—H13B0.96
C3—C41.4293 (14)C13—H13C0.96
C4—C61.4176 (14)C14—H14A0.999 (16)
C4—C51.4240 (14)C14—H14B1.011 (17)
C5—C91.4166 (14)C14—H14C0.998 (16)
C1—N—C5113.18 (9)C9—C8—C7119.74 (10)
C1—O1—C10105.92 (8)O3—C9—C8120.14 (9)
C3—O2—C12118.42 (8)O3—C9—C5118.84 (9)
C9—O3—C13114.67 (8)C8—C9—C5120.86 (10)
C8—O4—C14117.11 (8)C11—C10—O1112.47 (10)
N—C1—O1119.20 (10)C11—C10—H10131.6 (9)
N—C1—C2130.83 (10)O1—C10—H10115.9 (9)
O1—C1—C2109.97 (9)C10—C11—C2106.69 (10)
C3—C2—C1115.41 (10)C10—C11—H11124.8 (8)
C3—C2—C11139.63 (10)C2—C11—H11128.5 (8)
C1—C2—C11104.96 (9)O2—C12—H12A111.6 (9)
O2—C3—C2126.98 (10)O2—C12—H12B105.0 (9)
O2—C3—C4115.10 (9)H12A—C12—H12B110.1 (12)
C2—C3—C4117.91 (9)O2—C12—H12C111.3 (10)
C6—C4—C5118.76 (9)H12A—C12—H12C108.8 (12)
C6—C4—C3122.00 (9)H12B—C12—H12C110.1 (13)
C5—C4—C3119.23 (9)O3—C13—H13A109.5
N—C5—C9117.59 (9)O3—C13—H13B109.5
N—C5—C4123.40 (10)H13A—C13—H13B109.5
C9—C5—C4119.01 (9)O3—C13—H13C109.5
C7—C6—C4121.18 (10)H13A—C13—H13C109.5
C7—C6—H6119.3 (8)H13B—C13—H13C109.5
C4—C6—H6119.5 (8)O4—C14—H14A110.7 (9)
C6—C7—C8120.38 (9)O4—C14—H14B103.9 (8)
C6—C7—H7121.3 (9)H14A—C14—H14B111.1 (12)
C8—C7—H7118.3 (9)O4—C14—H14C109.7 (9)
O4—C8—C9116.07 (9)H14A—C14—H14C111.1 (12)
O4—C8—C7124.19 (9)H14B—C14—H14C110.1 (12)
C5—N—C1—O1179.22 (8)C6—C7—C8—O4178.33 (9)
C5—N—C1—C21.00 (16)C6—C7—C8—C90.90 (15)
C10—O1—C1—N179.69 (9)C13—O3—C9—C891.14 (11)
C10—O1—C1—C20.13 (11)C13—O3—C9—C593.42 (11)
N—C1—C2—C30.10 (17)O4—C8—C9—O35.38 (14)
O1—C1—C2—C3179.89 (8)C7—C8—C9—O3173.90 (8)
N—C1—C2—C11179.60 (11)O4—C8—C9—C5179.27 (8)
O1—C1—C2—C110.19 (11)C7—C8—C9—C51.45 (15)
C12—O2—C3—C20.09 (15)N—C5—C9—O36.65 (14)
C12—O2—C3—C4179.76 (8)C4—C5—C9—O3172.47 (8)
C1—C2—C3—O2178.01 (9)N—C5—C9—C8177.94 (8)
C11—C2—C3—O21.6 (2)C4—C5—C9—C82.94 (15)
C1—C2—C3—C41.65 (14)C1—O1—C10—C110.02 (12)
C11—C2—C3—C4178.79 (11)O1—C10—C11—C20.10 (12)
O2—C3—C4—C62.33 (14)C3—C2—C11—C10179.76 (13)
C2—C3—C4—C6177.97 (9)C1—C2—C11—C100.17 (11)
O2—C3—C4—C5177.27 (8)N—O1—O2—O32.22 (3)
C2—C3—C4—C52.43 (14)O1—O2—O3—O4173.67 (3)
C1—N—C5—C9179.19 (8)O2—O3—O4—C14.96 (3)
C1—N—C5—C40.11 (14)O3—O4—C1—C2172.58 (8)
C6—C4—C5—N178.82 (9)O4—C1—C2—C30.54 (10)
C3—C4—C5—N1.57 (15)C1—C2—C3—C41.65 (14)
C6—C4—C5—C92.11 (14)C2—C3—C4—C52.43 (14)
C3—C4—C5—C9177.50 (8)C3—C4—C5—C6179.61 (15)
C5—C4—C6—C70.18 (15)C4—C5—C6—C7179.85 (13)
C3—C4—C6—C7179.77 (9)C5—C6—C7—C81.61 (10)
C4—C6—C7—C81.70 (16)C6—C7—C8—C90.90 (15)
C14—O4—C8—C9172.41 (9)C7—C8—C9—C101.95 (16)
C14—O4—C8—C76.84 (14)C8—C9—C10—C113.84 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O3i0.97 (1)2.47 (1)3.315 (1)144.8 (11)
C12—H12A···O3ii0.99 (1)2.54 (1)3.159 (1)120.3 (11)
C10—H10···Ni0.97 (1)2.53 (1)3.290 (1)134.9 (11)
C14—H14A···Niii0.99 (1)2.69 (1)3.403 (1)128.0 (11)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1, z; (iii) x, y+3/2, z1/2.
 

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