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The title mol­ecule, bergapten, a psoralen/furan­ocoumarin derivative, possesses photocarcinogenic and photomutagenic activity. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016011221/su5310sup1.cif
Contains datablocks I, Global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011221/su5310Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016011221/su5310Isup3.cml
Supplementary material

CCDC reference: 1491854

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.055
  • wR factor = 0.138
  • Data-to-parameter ratio = 48.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00591 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.294 Check
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed .. ! Info PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 2 Note PLAT931_ALERT_5_G Found Twin Law ( 0 0 1)[ ] Estimated BASF 0.40 Check PLAT996_ALERT_1_G Non-Standard SHELXL LIST 4 Style FCF Supplied .. ! Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

4-Methoxy-7H-furo[3,2-g]chromen-7-one top
Crystal data top
C12H8O4Dx = 1.508 Mg m3
Mr = 216.18Melting point: 469 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 3.8486 (8) ÅCell parameters from 870 reflections
b = 14.676 (2) Åθ = 2.8–27.9°
c = 16.866 (3) ŵ = 0.12 mm1
β = 92.12 (2)°T = 299 K
V = 952.0 (3) Å3Needle, colourless
Z = 40.44 × 0.08 × 0.02 mm
F(000) = 448
Data collection top
Oxford Diffraction Xcalibur with a Sapphire CCD detector
diffractometer
7096 independent reflections
Radiation source: fine-focus sealed tube3811 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.08
Rotation method data acquisition using ω and phi scans.θmax = 25.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)'
h = 44
Tmin = 0.951, Tmax = 0.998k = 1717
7096 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.0738P)2]
where P = (Fo2 + 2Fc2)/3
7096 reflections(Δ/σ)max = 0.002
147 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7447 (9)0.00489 (18)0.37565 (18)0.0525 (10)
O20.3156 (8)0.26727 (18)0.50579 (14)0.0399 (9)
O30.7860 (9)0.28906 (17)0.24893 (16)0.0510 (10)
O40.1046 (9)0.3863 (2)0.56614 (18)0.0617 (11)
C10.6682 (13)0.0956 (3)0.3822 (3)0.0392 (13)
C20.8854 (13)0.0043 (3)0.3016 (3)0.0534 (15)
H20.96190.05950.28140.064*
C30.8989 (13)0.0740 (3)0.2626 (3)0.0477 (14)
H30.98320.08330.21230.057*
C40.7573 (13)0.1417 (3)0.3137 (2)0.0369 (12)
C50.6975 (12)0.2354 (3)0.3111 (2)0.0344 (12)
C60.5523 (11)0.2781 (3)0.3757 (2)0.0304 (11)
C70.4677 (11)0.2262 (3)0.4418 (2)0.0348 (12)
C80.5234 (12)0.1339 (3)0.4477 (3)0.0397 (13)
H80.46790.10030.49220.048*
C90.4692 (12)0.3738 (3)0.3771 (3)0.0373 (13)
H90.52210.41010.33390.045*
C100.3191 (12)0.4114 (3)0.4385 (2)0.0431 (13)
H100.26540.47320.43710.052*
C110.2370 (13)0.3592 (3)0.5074 (3)0.0433 (13)
C120.6549 (14)0.2653 (3)0.1726 (2)0.0652 (17)
H12A0.79360.21730.15160.098*
H12B0.66300.31750.13840.098*
H12C0.41870.24500.17580.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.075 (3)0.0265 (17)0.056 (2)0.0074 (19)0.006 (2)0.0024 (16)
O20.054 (2)0.0343 (18)0.0321 (16)0.0034 (18)0.0073 (19)0.0003 (14)
O30.081 (3)0.0419 (18)0.0300 (17)0.0206 (19)0.005 (2)0.0006 (15)
O40.089 (3)0.052 (2)0.045 (2)0.018 (2)0.025 (2)0.0027 (18)
C10.045 (4)0.029 (3)0.043 (3)0.000 (3)0.007 (3)0.000 (2)
C20.063 (4)0.040 (3)0.058 (3)0.009 (3)0.010 (3)0.013 (3)
C30.054 (4)0.041 (3)0.048 (3)0.001 (3)0.007 (3)0.006 (2)
C40.040 (3)0.032 (3)0.039 (3)0.002 (3)0.001 (3)0.0073 (19)
C50.036 (3)0.037 (3)0.030 (2)0.006 (3)0.001 (3)0.001 (2)
C60.029 (3)0.029 (2)0.033 (2)0.002 (2)0.002 (2)0.001 (2)
C70.041 (3)0.033 (3)0.031 (2)0.002 (3)0.005 (2)0.002 (2)
C80.049 (4)0.033 (3)0.038 (3)0.002 (3)0.004 (3)0.008 (2)
C90.047 (3)0.030 (3)0.035 (3)0.004 (2)0.002 (3)0.005 (2)
C100.056 (4)0.029 (2)0.044 (3)0.004 (3)0.001 (3)0.003 (2)
C110.046 (4)0.036 (3)0.048 (3)0.007 (3)0.006 (3)0.001 (2)
C120.099 (5)0.060 (3)0.037 (3)0.013 (4)0.001 (3)0.003 (2)
Geometric parameters (Å, º) top
O1—C11.369 (5)C4—C51.394 (6)
O1—C21.386 (5)C5—C61.391 (5)
O2—C71.385 (4)C6—C71.398 (5)
O2—C111.383 (5)C6—C91.442 (5)
O3—C51.365 (4)C7—C81.374 (5)
O3—C121.409 (4)C8—H80.9300
O4—C111.200 (5)C9—C101.325 (5)
C1—C81.376 (5)C9—H90.9300
C1—C41.393 (6)C10—C111.435 (5)
C2—C31.327 (6)C10—H100.9300
C2—H20.9300C12—H12A0.9600
C3—C41.435 (6)C12—H12B0.9600
C3—H30.9300C12—H12C0.9600
C1—O1—C2105.1 (3)C8—C7—O2116.2 (4)
C7—O2—C11122.6 (3)C8—C7—C6123.7 (4)
C5—O3—C12117.9 (3)O2—C7—C6120.1 (4)
O1—C1—C8123.8 (4)C1—C8—C7114.2 (4)
O1—C1—C4110.2 (4)C1—C8—H8122.9
C8—C1—C4126.0 (4)C7—C8—H8122.9
C3—C2—O1112.7 (4)C10—C9—C6121.4 (4)
C3—C2—H2123.7C10—C9—H9119.3
O1—C2—H2123.7C6—C9—H9119.3
C2—C3—C4106.2 (4)C9—C10—C11121.7 (4)
C2—C3—H3126.9C9—C10—H10119.1
C4—C3—H3126.9C11—C10—H10119.1
C5—C4—C1117.3 (4)O4—C11—O2116.1 (4)
C5—C4—C3136.9 (4)O4—C11—C10127.2 (4)
C1—C4—C3105.8 (4)O2—C11—C10116.8 (4)
O3—C5—C6117.4 (4)O3—C12—H12A109.5
O3—C5—C4123.2 (4)O3—C12—H12B109.5
C6—C5—C4119.4 (4)H12A—C12—H12B109.5
C5—C6—C7119.4 (4)O3—C12—H12C109.5
C5—C6—C9123.2 (4)H12A—C12—H12C109.5
C7—C6—C9117.4 (4)H12B—C12—H12C109.5
C2—O1—C1—C8179.8 (5)C4—C5—C6—C9177.6 (4)
C2—O1—C1—C40.3 (5)C11—O2—C7—C8178.5 (4)
C1—O1—C2—C30.2 (6)C11—O2—C7—C60.9 (6)
O1—C2—C3—C40.0 (6)C5—C6—C7—C80.8 (6)
O1—C1—C4—C5179.6 (4)C9—C6—C7—C8178.3 (4)
C8—C1—C4—C50.5 (7)C5—C6—C7—O2178.5 (4)
O1—C1—C4—C30.3 (5)C9—C6—C7—O21.1 (6)
C8—C1—C4—C3179.8 (5)O1—C1—C8—C7179.9 (5)
C2—C3—C4—C5179.2 (6)C4—C1—C8—C70.1 (7)
C2—C3—C4—C10.2 (6)O2—C7—C8—C1178.7 (4)
C12—O3—C5—C6126.8 (4)C6—C7—C8—C10.6 (7)
C12—O3—C5—C455.5 (6)C5—C6—C9—C10177.4 (5)
C1—C4—C5—O3177.3 (4)C7—C6—C9—C100.1 (7)
C3—C4—C5—O31.7 (9)C6—C9—C10—C111.1 (7)
C1—C4—C5—C60.3 (7)C7—O2—C11—O4179.7 (4)
C3—C4—C5—C6179.3 (5)C7—O2—C11—C100.3 (6)
O3—C5—C6—C7178.0 (4)C9—C10—C11—O4179.3 (5)
C4—C5—C6—C70.3 (6)C9—C10—C11—O21.3 (7)
O3—C5—C6—C94.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.932.493.406 (5)170
C3—H3···O4ii0.932.573.484 (6)170
C10—H10···O4iii0.932.513.387 (5)158
C12—H12A···O4ii0.962.443.376 (5)165
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y+1/2, z1/2; (iii) x, y+1, z+1.
 

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