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The title compound (alternative name 5,8-di­methoxy­psoralen), C13H10O5, is a natural product extracted from Adiscanthus fusciflorus (Rutaceae). Our biochemical tests show that this compound 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/S1600536803019925/ac6055sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019925/ac6055Isup2.hkl
Contains datablock I

CCDC reference: 225769

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.124
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H10 O5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

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
C13H10O5F(000) = 512
Mr = 246.21Dx = 1.53 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2772 reflections
a = 16.9357 (5) Åθ = 1.0–27.5°
b = 4.3669 (1) ŵ = 0.12 mm1
c = 16.2558 (4) ÅT = 120 K
β = 117.218 (1)°Prism, light yellow
V = 1069.10 (5) Å30.28 × 0.16 × 0.05 mm
Z = 4
Data collection top
KappaCCD
diffractometer
Rint = 0.023
φ and ω scansθmax = 27.5°, θmin = 2.5°
4114 measured reflectionsh = 2122
2450 independent reflectionsk = 45
1841 reflections with I > 2σ(I)l = 2120
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0713P)2 + 0.1752P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.124(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.23 e Å3
2450 reflectionsΔρmin = 0.3 e Å3
197 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
O10.25821 (7)0.3321 (2)0.15311 (7)0.0290 (3)
O20.08783 (6)1.0025 (3)0.24125 (7)0.0324 (3)
O30.33339 (8)0.0004 (2)0.11387 (8)0.0366 (3)
O40.09680 (7)0.6081 (3)0.10486 (7)0.0350 (3)
O50.39331 (6)0.8340 (2)0.44430 (7)0.0268 (3)
C10.33592 (11)0.1792 (3)0.17207 (10)0.0288 (3)
C20.41263 (10)0.2493 (3)0.25869 (11)0.0283 (3)
C30.40727 (9)0.4432 (3)0.31994 (10)0.0249 (3)
C40.32509 (9)0.5916 (3)0.30127 (9)0.0231 (3)
C50.31677 (9)0.7921 (3)0.36502 (9)0.0231 (3)
C60.23412 (9)0.9258 (3)0.34167 (9)0.0239 (3)
C70.16400 (9)0.8570 (3)0.25405 (10)0.0268 (3)
C80.16904 (9)0.6663 (3)0.18827 (10)0.0271 (3)
C90.25149 (9)0.5312 (3)0.21538 (10)0.0248 (3)
C100.19474 (10)1.1281 (4)0.38392 (11)0.0289 (3)
C110.10984 (10)1.1639 (4)0.32247 (11)0.0336 (4)
C120.39212 (10)1.0369 (4)0.51305 (10)0.0271 (3)
C130.09892 (11)0.7760 (4)0.02912 (11)0.0371 (4)
H12A0.3524 (14)0.951 (5)0.5385 (13)0.056*
H12B0.4561 (14)1.050 (5)0.5612 (13)0.056*
H12C0.3734 (13)1.249 (5)0.4877 (13)0.056*
H13A0.1549 (14)0.721 (5)0.0262 (13)0.056*
H13B0.0463 (14)0.713 (5)0.0271 (14)0.056*
H13C0.0966 (13)1.003 (6)0.0418 (13)0.056*
H30.4575 (11)0.486 (4)0.3790 (11)0.028 (4)*
H20.4666 (12)0.144 (4)0.2690 (11)0.034 (4)*
H110.0613 (11)1.279 (4)0.3229 (11)0.032 (4)*
H100.2229 (11)1.225 (4)0.4447 (12)0.035 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0350 (6)0.0248 (5)0.0288 (5)0.0057 (4)0.0159 (5)0.0061 (4)
O20.0219 (5)0.0350 (6)0.0388 (6)0.0003 (4)0.0127 (4)0.0017 (5)
O30.0556 (7)0.0274 (6)0.0362 (6)0.0048 (5)0.0292 (5)0.0063 (5)
O40.0284 (5)0.0386 (6)0.0300 (6)0.0096 (5)0.0065 (4)0.0029 (5)
O50.0241 (5)0.0284 (6)0.0247 (5)0.0007 (4)0.0084 (4)0.0040 (4)
C10.0405 (8)0.0210 (7)0.0331 (8)0.0032 (6)0.0239 (7)0.0006 (6)
C20.0334 (8)0.0228 (7)0.0352 (8)0.0001 (6)0.0213 (7)0.0009 (6)
C30.0266 (7)0.0213 (7)0.0290 (7)0.0032 (6)0.0146 (6)0.0012 (6)
C40.0250 (7)0.0204 (7)0.0255 (7)0.0041 (5)0.0129 (6)0.0005 (6)
C50.0224 (6)0.0206 (7)0.0256 (7)0.0036 (5)0.0105 (6)0.0010 (6)
C60.0241 (7)0.0208 (7)0.0278 (7)0.0036 (6)0.0126 (6)0.0004 (6)
C70.0222 (7)0.0250 (7)0.0338 (8)0.0025 (6)0.0134 (6)0.0018 (6)
C80.0241 (7)0.0278 (8)0.0256 (7)0.0081 (6)0.0082 (6)0.0023 (6)
C90.0304 (7)0.0209 (7)0.0260 (7)0.0059 (6)0.0155 (6)0.0026 (6)
C100.0292 (7)0.0272 (8)0.0337 (8)0.0004 (6)0.0173 (6)0.0013 (6)
C110.0289 (7)0.0354 (9)0.0398 (8)0.0015 (7)0.0186 (7)0.0019 (7)
C120.0314 (8)0.0244 (7)0.0248 (7)0.0012 (6)0.0122 (6)0.0029 (6)
C130.0330 (9)0.0427 (10)0.0291 (8)0.0024 (8)0.0085 (7)0.0015 (7)
Geometric parameters (Å, º) top
O1—C91.3781 (17)C4—C51.412 (2)
O1—C11.3789 (19)C5—C61.3993 (19)
O2—C71.3658 (17)C6—C71.4078 (19)
O2—C111.3888 (19)C6—C101.455 (2)
O3—C11.2145 (18)C7—C81.388 (2)
O4—C81.3721 (17)C8—C91.389 (2)
O4—C131.447 (2)C10—C111.333 (2)
O5—C51.3590 (16)C10—H100.976 (18)
O5—C121.4336 (17)C11—H110.966 (18)
C1—C21.446 (2)C12—H12A1.01 (2)
C2—C31.341 (2)C12—H12B1.01 (2)
C2—H20.966 (18)C12—H12C1.00 (2)
C3—C41.436 (2)C13—H13A1.00 (2)
C3—H30.967 (16)C13—H13B0.98 (2)
C4—C91.4072 (19)C13—H13C1.02 (2)
C9—O1—C1122.16 (11)O4—C8—C7122.09 (13)
C7—O2—C11105.49 (11)O4—C8—C9123.19 (13)
C8—O4—C13112.89 (11)C7—C8—C9114.68 (13)
C5—O5—C12118.37 (11)O1—C9—C8116.35 (12)
O3—C1—O1116.64 (14)O1—C9—C4120.91 (13)
O3—C1—C2126.23 (14)C8—C9—C4122.74 (13)
O1—C1—C2117.13 (12)C11—C10—C6106.74 (14)
C3—C2—C1121.37 (14)C11—C10—H10124.6 (10)
C3—C2—H2123.4 (10)C6—C10—H10128.7 (10)
C1—C2—H2115.2 (10)C10—C11—O2112.42 (14)
C2—C3—C4121.06 (14)C10—C11—H11133.3 (10)
C2—C3—H3122.2 (10)O2—C11—H11114.3 (10)
C4—C3—H3116.7 (10)O5—C12—H12A109.8 (12)
C9—C4—C5120.26 (13)O5—C12—H12B104.3 (12)
C9—C4—C3117.27 (13)H12A—C12—H12B112.6 (16)
C5—C4—C3122.48 (13)O5—C12—H12C111.4 (11)
O5—C5—C6127.08 (12)H12A—C12—H12C111.6 (17)
O5—C5—C4114.05 (12)H12B—C12—H12C106.9 (17)
C6—C5—C4118.87 (12)O4—C13—H13A108.2 (12)
C5—C6—C7117.50 (13)O4—C13—H13B106.6 (12)
C5—C6—C10137.99 (13)H13A—C13—H13B111.5 (16)
C7—C6—C10104.50 (12)O4—C13—H13C107.7 (11)
O2—C7—C8123.24 (13)H13A—C13—H13C111.6 (17)
O2—C7—C6110.85 (12)H13B—C13—H13C111.1 (17)
C8—C7—C6125.91 (13)
C9—O1—C1—O3177.04 (12)C6—C7—C8—C91.5 (2)
C9—O1—C1—C23.43 (19)C1—O1—C9—C8178.98 (12)
O3—C1—C2—C3177.32 (14)C1—O1—C9—C41.16 (19)
O1—C1—C2—C33.2 (2)O4—C8—C9—O10.4 (2)
C1—C2—C3—C40.7 (2)C7—C8—C9—O1177.84 (12)
C2—C3—C4—C91.7 (2)O4—C8—C9—C4179.73 (12)
C2—C3—C4—C5178.70 (13)C7—C8—C9—C42.3 (2)
C12—O5—C5—C60.3 (2)C5—C4—C9—O1178.89 (12)
C12—O5—C5—C4179.20 (11)C3—C4—C9—O11.45 (19)
C9—C4—C5—O5178.82 (12)C5—C4—C9—C81.3 (2)
C3—C4—C5—O50.82 (19)C3—C4—C9—C8178.39 (13)
C9—C4—C5—C60.8 (2)C5—C6—C10—C11179.33 (17)
C3—C4—C5—C6179.60 (12)C7—C6—C10—C110.24 (16)
O5—C5—C6—C7178.03 (13)C6—C10—C11—O20.09 (18)
C4—C5—C6—C71.49 (19)C7—O2—C11—C100.40 (17)
O5—C5—C6—C103.0 (3)O1—O2—O4—O52.02 (5)
C4—C5—C6—C10177.52 (16)O2—O4—O5—C1177.46 (5)
C11—O2—C7—C8178.94 (14)O4—O5—C1—C2177.19 (11)
C11—O2—C7—C60.55 (15)O5—C1—C2—C30.57 (9)
C5—C6—C7—O2179.81 (12)C1—C2—C3—C40.7 (2)
C10—C6—C7—O20.50 (15)C2—C3—C4—C5178.70 (13)
C5—C6—C7—C80.3 (2)C3—C4—C5—C6179.60 (12)
C10—C6—C7—C8178.98 (14)C4—C5—C6—C71.49 (19)
C13—O4—C8—C7103.24 (16)C5—C6—C7—C80.3 (2)
C13—O4—C8—C979.52 (18)C6—C7—C8—C91.5 (2)
O2—C7—C8—O40.4 (2)C7—C8—C9—C100.14 (9)
C6—C7—C8—O4179.00 (13)C8—C9—C10—C111.91 (12)
O2—C7—C8—C9177.88 (12)C9—C10—C11—C1227.4 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O5i1.01 (2)2.64 (2)3.420 (1)134.2 (14)
C13—H13B···O4ii0.98 (2)2.58 (2)3.455 (2)149.4 (16)
C12—H12A···O3iii1.01 (2)2.41 (2)3.264 (1)141.3 (16)
C12—H12C···O3iv1.00 (2)2.67 (2)3.043 (1)102.0 (13)
C11—H11···O2v0.96 (1)2.45 (1)3.360 (1)156.7 (13)
Symmetry codes: (i) x+1, y2, z+1; (ii) x, y1, z; (iii) x, y1/2, z+1/2; (iv) x, y3/2, z+1/2; (v) x, y1/2, z+1/2.
 

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