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Unlike a previously reported structure for racemic naringenin [systematic name: 2,3-di­hydro-5,6-di­hydroxy-2-(4-hydroxy­phenyl)-4H-1-benzo­pyran-4-one], C15H12O5, both S and R enantiomers appear to occupy somewhat randomly the four crystallographic sites of the unit cell in an approximate 3:1/1:3 ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680202278X/cf6230sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680202278X/cf6230Isup2.hkl
Contains datablock I

CCDC reference: 202996

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.067
  • wR factor = 0.155
  • Data-to-parameter ratio = 15.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
RINTA_01 Alert B The value of Rint is greater than 0.15 Rint given 0.158
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek,2001).

2,3-Dihydro-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one top
Crystal data top
C15H12O5F(000) = 568
Mr = 272.25Dx = 1.482 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 4.8740 (5) ÅCell parameters from 13970 reflections
b = 15.2610 (15) Åθ = 2.9–27.5°
c = 16.423 (2) ŵ = 0.11 mm1
β = 92.375 (5)°T = 120 K
V = 1220.5 (2) Å3Needle, colourless
Z = 40.38 × 0.06 × 0.04 mm
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
2701 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode1099 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.158
Detector resolution: 3.89 pixels mm-1θmax = 27.5°, θmin = 3.7°
φ and ω scansh = 66
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
k = 1819
Tmin = 0.959, Tmax = 0.996l = 2020
11748 measured reflections
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
2701 reflections(Δ/σ)max < 0.001
170 parametersΔρmax = 0.21 e Å3
20 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.6345 (4)0.53263 (14)0.34853 (13)0.0308 (6)
O20.1441 (5)0.31118 (16)0.20343 (14)0.0363 (6)
H20.09900.29980.25110.044*
O30.7955 (5)0.47286 (17)0.06527 (14)0.0425 (7)
H30.92020.51020.07370.051*
O41.0686 (5)0.59448 (17)0.14732 (14)0.0394 (7)
O5A0.9458 (11)0.7747 (3)0.6503 (3)0.033 (2)*0.775 (8)
H5A0.82000.81220.65200.039*0.775 (8)
C2A0.8986 (9)0.5767 (3)0.3593 (3)0.0302 (14)*0.775 (8)
H2A1.04400.53080.36600.036*0.775 (8)
C3A0.9565 (15)0.6295 (5)0.2838 (4)0.037 (3)*0.775 (8)
H3A0.82570.67900.27920.045*0.775 (8)
H3B1.14420.65420.28950.045*0.775 (8)
C1A'0.8991 (12)0.6294 (3)0.4359 (3)0.0270 (13)*0.775 (8)
C2A'0.7198 (11)0.6976 (4)0.4453 (3)0.0330 (14)*0.775 (8)
H2A'0.58660.71040.40310.040*0.775 (8)
C3A'0.7304 (12)0.7485 (4)0.5160 (3)0.0336 (17)*0.775 (8)
H3A'0.60740.79620.52160.040*0.775 (8)
C4A'0.9202 (19)0.7290 (7)0.5775 (4)0.0261 (14)*0.775 (8)
C5A'1.1014 (13)0.6611 (5)0.5693 (4)0.0358 (16)*0.775 (8)
H5A'1.23320.64830.61180.043*0.775 (8)
C6A'1.0914 (11)0.6114 (3)0.4986 (3)0.0321 (14)*0.775 (8)
H6A'1.21730.56450.49300.038*0.775 (8)
O5B0.899 (4)0.7676 (12)0.6539 (9)0.031 (7)*0.225 (8)
H5B0.88800.82240.65050.038*0.225 (8)
C2B0.756 (3)0.6186 (10)0.3414 (8)0.025 (5)*0.225 (8)
H2B0.61380.65680.31350.030*0.225 (8)
C3B1.002 (4)0.6187 (16)0.2887 (12)0.018 (7)*0.225 (8)
H3X1.15500.58670.31680.022*0.225 (8)
H3Y1.06230.67970.27970.022*0.225 (8)
C1B'0.803 (4)0.6545 (13)0.4257 (8)0.029 (3)*0.225 (8)
C2B'0.653 (4)0.7248 (12)0.4493 (9)0.029 (3)*0.225 (8)
H2B'0.52060.74940.41180.035*0.225 (8)
C3B'0.686 (4)0.7607 (14)0.5248 (10)0.029 (3)*0.225 (8)
H3B'0.56600.80580.54130.035*0.225 (8)
C4B'0.892 (7)0.732 (2)0.5768 (14)0.029 (3)*0.225 (8)
C5B'1.057 (4)0.6613 (15)0.5576 (11)0.029 (3)*0.225 (8)
H5B'1.19520.63960.59480.035*0.225 (8)
C6B'1.008 (4)0.6231 (11)0.4788 (10)0.029 (3)*0.225 (8)
H6B'1.11810.57520.46270.035*0.225 (8)
C40.9327 (7)0.5759 (2)0.2079 (2)0.0303 (9)
C50.6660 (7)0.4584 (2)0.1346 (2)0.0332 (9)
C60.4647 (7)0.3942 (2)0.1341 (2)0.0346 (9)
H60.41600.36310.08550.041*
C70.3366 (7)0.3765 (2)0.2055 (2)0.0299 (9)
C80.3964 (6)0.4220 (2)0.2772 (2)0.0295 (9)
H80.30510.40820.32560.035*
C90.5906 (6)0.4876 (2)0.2770 (2)0.0276 (9)
C100.7324 (6)0.5072 (2)0.2061 (2)0.0284 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0330 (14)0.0286 (15)0.0307 (15)0.0057 (11)0.0010 (11)0.0028 (11)
O20.0407 (14)0.0354 (15)0.0325 (15)0.0077 (12)0.0008 (12)0.0027 (13)
O30.0478 (17)0.053 (2)0.0277 (15)0.0108 (13)0.0086 (13)0.0055 (12)
O40.0477 (16)0.0389 (16)0.0321 (15)0.0048 (12)0.0106 (13)0.0006 (13)
C40.034 (2)0.030 (2)0.027 (2)0.0077 (17)0.0029 (17)0.0022 (17)
C50.035 (2)0.036 (2)0.030 (2)0.0053 (18)0.0042 (18)0.0001 (18)
C60.039 (2)0.035 (2)0.029 (2)0.0012 (18)0.0041 (18)0.0023 (18)
C70.0274 (19)0.028 (2)0.033 (2)0.0036 (17)0.0038 (17)0.0027 (17)
C80.0263 (19)0.034 (2)0.028 (2)0.0019 (17)0.0006 (15)0.0006 (18)
C90.0263 (19)0.025 (2)0.031 (2)0.0058 (16)0.0033 (17)0.0031 (17)
C100.0251 (18)0.029 (2)0.031 (2)0.0007 (16)0.0021 (16)0.0017 (17)
Geometric parameters (Å, º) top
O1—C91.370 (4)O5B—H5B0.840
O1—C2B1.446 (14)C2B—C3B1.508 (15)
O1—C2A1.457 (5)C2B—C1B'1.499 (14)
O2—C71.368 (4)C2B—H2B1.000
O2—H20.840C3B—C41.50 (2)
O3—C51.343 (4)C3B—H3X0.990
O3—H30.840C3B—H3Y0.990
O4—C41.251 (4)C1B'—C2B'1.365 (16)
O5A—C4A'1.385 (5)C1B'—C6B'1.384 (16)
O5A—H5A0.840C2B'—C3B'1.359 (15)
C2A—C3A1.515 (7)C2B'—H2B'0.950
C2A—C1A'1.493 (6)C3B'—C4B'1.363 (15)
C2A—H2A1.000C3B'—H3B'0.950
C3A—C41.491 (8)C4B'—C5B'1.388 (15)
C3A—H3A0.990C5B'—C6B'1.431 (15)
C3A—H3B0.990C5B'—H5B'0.950
C1A'—C2A'1.372 (6)C6B'—H6B'0.950
C1A'—C6A'1.391 (6)C4—C101.432 (5)
C2A'—C3A'1.396 (6)C5—C61.386 (5)
C2A'—H2A'0.950C5—C101.417 (5)
C3A'—C4A'1.374 (6)C6—C71.378 (5)
C3A'—H3A'0.950C6—H60.950
C4A'—C5A'1.371 (6)C7—C81.388 (5)
C5A'—C6A'1.386 (6)C8—C91.378 (5)
C5A'—H5A'0.950C8—H80.950
C6A'—H6A'0.950C9—C101.411 (4)
O5B—C4B'1.378 (14)
C9—O1—C2B115.8 (5)C2B—C3B—H3Y109.5
C9—O1—C2A116.2 (3)C4—C3B—H3Y109.5
C7—O2—H2109.5H3X—C3B—H3Y108.1
C5—O3—H3109.5C2B'—C1B'—C6B'118.4 (12)
C4A'—O5A—H5A109.5C2B'—C1B'—C2B119.0 (14)
O1—C2A—C3A109.9 (4)C6B'—C1B'—C2B122.4 (15)
O1—C2A—C1A'108.8 (3)C3B'—C2B'—C1B'122.0 (14)
C3A—C2A—C1A'114.2 (4)C3B'—C2B'—H2B'119.0
O1—C2A—H2A107.9C1B'—C2B'—H2B'119.0
C3A—C2A—H2A107.9C2B'—C3B'—C4B'119.9 (16)
C1A'—C2A—H2A107.9C2B'—C3B'—H3B'120.1
C4—C3A—C2A112.5 (5)C4B'—C3B'—H3B'120.1
C4—C3A—H3A109.1C3B'—C4B'—O5B116.0 (15)
C2A—C3A—H3A109.1C3B'—C4B'—C5B'121.8 (15)
C4—C3A—H3B109.1O5B—C4B'—C5B'121.4 (16)
C2A—C3A—H3B109.1C4B'—C5B'—C6B'116.4 (15)
H3A—C3A—H3B107.8C4B'—C5B'—H5B'121.8
C2A'—C1A'—C6A'118.7 (4)C6B'—C5B'—H5B'121.8
C2A'—C1A'—C2A121.6 (5)C1B'—C6B'—C5B'121.1 (14)
C6A'—C1A'—C2A119.6 (5)C1B'—C6B'—H6B'119.4
C1A'—C2A'—C3A'120.9 (5)C5B'—C6B'—H6B'119.4
C1A'—C2A'—H2A'119.5O4—C4—C10122.1 (3)
C3A'—C2A'—H2A'119.5O4—C4—C3A121.0 (4)
C4A'—C3A'—C2A'119.4 (5)C10—C4—C3A116.6 (4)
C4A'—C3A'—H3A'120.3O4—C4—C3B119.8 (7)
C2A'—C3A'—H3A'120.3C10—C4—C3B117.7 (7)
C5A'—C4A'—C3A'120.5 (5)O3—C5—C6118.0 (3)
C5A'—C4A'—O5A115.5 (5)O3—C5—C10121.1 (3)
C3A'—C4A'—O5A124.0 (5)C6—C5—C10120.9 (3)
C4A'—C5A'—C6A'119.7 (5)C7—C6—C5118.6 (3)
C4A'—C5A'—H5A'120.1C7—C6—H6120.7
C6A'—C5A'—H5A'120.1C5—C6—H6120.7
C5A'—C6A'—C1A'120.7 (4)O2—C7—C6117.1 (3)
C5A'—C6A'—H6A'119.7O2—C7—C8120.4 (3)
C1A'—C6A'—H6A'119.7C6—C7—C8122.5 (3)
C4B'—O5B—H5B109.5C9—C8—C7118.8 (3)
C3B—C2B—O1112.6 (13)C9—C8—H8120.6
C3B—C2B—C1B'115.7 (13)C7—C8—H8120.6
O1—C2B—C1B'107.8 (11)O1—C9—C8116.4 (3)
C3B—C2B—H2B106.8O1—C9—C10122.5 (3)
O1—C2B—H2B106.8C8—C9—C10121.1 (3)
C1B'—C2B—H2B106.8C9—C10—C5118.0 (3)
C2B—C3B—C4110.6 (13)C9—C10—C4119.7 (3)
C2B—C3B—H3X109.5C5—C10—C4122.3 (3)
C4—C3B—H3X109.5
C9—O1—C2A—C3A48.7 (5)C2B'—C1B'—C6B'—C5B'2 (3)
C9—O1—C2A—C1A'174.3 (3)C2B—C1B'—C6B'—C5B'177.0 (18)
O1—C2A—C3A—C453.1 (7)C4B'—C5B'—C6B'—C1B'1 (4)
C1A'—C2A—C3A—C4175.6 (5)C2A—C3A—C4—O4151.8 (4)
O1—C2A—C1A'—C2A'62.8 (5)C2A—C3A—C4—C1032.9 (7)
C3A—C2A—C1A'—C2A'60.3 (6)C2B—C3B—C4—O4156.0 (12)
O1—C2A—C1A'—C6A'119.4 (4)C2B—C3B—C4—C1031 (2)
C3A—C2A—C1A'—C6A'117.5 (6)O3—C5—C6—C7177.8 (3)
C6A'—C1A'—C2A'—C3A'0.4 (8)C10—C5—C6—C72.3 (5)
C2A—C1A'—C2A'—C3A'177.4 (5)C5—C6—C7—O2178.3 (3)
C1A'—C2A'—C3A'—C4A'1.1 (11)C5—C6—C7—C81.7 (5)
C2A'—C3A'—C4A'—C5A'1.1 (15)O2—C7—C8—C9179.8 (3)
C2A'—C3A'—C4A'—O5A179.4 (9)C6—C7—C8—C90.2 (5)
C3A'—C4A'—C5A'—C6A'0.6 (16)C2B—O1—C9—C8158.2 (7)
O5A—C4A'—C5A'—C6A'179.9 (8)C2A—O1—C9—C8157.5 (3)
C4A'—C5A'—C6A'—C1A'0.1 (11)C2B—O1—C9—C1020.9 (8)
C2A'—C1A'—C6A'—C5A'0.2 (8)C2A—O1—C9—C1023.3 (5)
C2A—C1A'—C6A'—C5A'178.0 (6)C7—C8—C9—O1177.6 (3)
C9—O1—C2B—C3B47.7 (15)C7—C8—C9—C101.6 (5)
C9—O1—C2B—C1B'176.5 (9)O1—C9—C10—C5178.1 (3)
O1—C2B—C3B—C452 (2)C8—C9—C10—C51.0 (5)
C1B'—C2B—C3B—C4176.3 (14)O1—C9—C10—C40.7 (5)
C3B—C2B—C1B'—C2B'120.7 (19)C8—C9—C10—C4179.9 (3)
O1—C2B—C1B'—C2B'112.3 (15)O3—C5—C10—C9179.1 (3)
C3B—C2B—C1B'—C6B'55 (2)C6—C5—C10—C91.0 (5)
O1—C2B—C1B'—C6B'72.4 (17)O3—C5—C10—C42.1 (5)
C6B'—C1B'—C2B'—C3B'4 (3)C6—C5—C10—C4177.9 (3)
C2B—C1B'—C2B'—C3B'179.8 (19)O4—C4—C10—C9178.3 (3)
C1B'—C2B'—C3B'—C4B'6 (4)C3A—C4—C10—C96.5 (6)
C2B'—C3B'—C4B'—O5B176 (3)C3B—C4—C10—C95.7 (12)
C2B'—C3B'—C4B'—C5B'5 (6)O4—C4—C10—C52.9 (5)
C3B'—C4B'—C5B'—C6B'3 (5)C3A—C4—C10—C5172.3 (5)
O5B—C4B'—C5B'—C6B'173 (3)C3B—C4—C10—C5175.5 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.841.892.624 (3)145
O2—H2···O5Ai0.842.002.788 (6)156
O5A—H5A···O4ii0.841.882.713 (6)172
O5B—H5B···O4ii0.842.012.651 (18)133
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1/2, y+3/2, z+1/2.
 

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