Disordered 6-hydroxy­flavanone

In contrast to the previously reported crystal structure of 6-hydroxy­flavanone [Shoja et al. (1998). Z. Kristallogr. New Cryst. Struct. 213, 373-374], in the title crystal structure, C₁₅H₁₂O₃, both S and R enanti­omers appear to occupy randomly the four crystallographic sites of the unit cell in an approximate 3:1/1:3 ratio.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.095
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT770_ALERT_2_A Suspect C-H Bond in CIF:      C2     -H3C     ..       1.53 Ang.

Author Response: C2 and H3C belong to two disordered enantiomers of titled compounds.

Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      28.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C6A'   ..  C6A'    ..       3.05 Ang.

Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11

   1 ALERT level A = In general: serious problem
   2 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1999); software used to prepare material for publication: SHELXL97.

6-hydroxyflavanone

Crystal data

C15H12O3	F(000) = 504
Mr = 240.25	Dx = 1.392 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6521 reflections
a = 5.251 (2) Å	θ = 3.5–28.4°
b = 21.809 (4) Å	µ = 0.10 mm^−1
c = 10.025 (3) Å	T = 100 K
β = 93.34 (3)°	Block, colourless
V = 1146.1 (6) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Kuma KM-4-CCD diffractometer	1456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 26.0°, θmin = 3.5°
ω scans	h = −6→6
7454 measured reflections	k = −26→26
2233 independent reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0531P)^2] where P = (Fo^2 + 2Fc^2)/3
2233 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.23 e Å^−3
163 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3495 (2)	0.56939 (5)	0.61820 (11)	0.0267 (3)
O2	−0.0853 (2)	0.71417 (5)	0.73598 (11)	0.0248 (3)
O3	0.5143 (2)	0.79817 (5)	0.39979 (10)	0.0237 (3)
H3H	0.6575	0.7973	0.3448	0.028*
C3	0.0311 (3)	0.60871 (7)	0.76399 (17)	0.0264 (4)
H3A	0.1399	0.6076	0.8480	0.032*	0.75
H3B	−0.1471	0.6014	0.7870	0.032*	0.75
H3C	−0.1226	0.5895	0.7284	0.032*	0.25
H3D	0.0168	0.6134	0.8585	0.032*	0.25
C4	0.0486 (3)	0.67144 (7)	0.70286 (15)	0.0195 (4)
C5	0.2878 (3)	0.73532 (7)	0.54479 (15)	0.0200 (4)
H5A	0.1922	0.7701	0.5695	0.024*
C6	0.4715 (3)	0.74157 (7)	0.45305 (15)	0.0188 (4)
C7	0.6093 (3)	0.69005 (7)	0.41596 (15)	0.0213 (4)
H7A	0.7357	0.6942	0.3525	0.026*
C8	0.5639 (3)	0.63334 (7)	0.47054 (15)	0.0221 (4)
H8A	0.6574	0.5986	0.4440	0.027*
C9	0.3807 (3)	0.62707 (7)	0.56467 (15)	0.0187 (4)
C10	0.2406 (3)	0.67792 (7)	0.60216 (15)	0.0180 (4)
C2	0.1114 (4)	0.55802 (10)	0.6745 (2)	0.0240 (5)	0.75
H2	−0.0203	0.5553	0.5986	0.029*	0.75
C1'	0.1257 (5)	0.49562 (11)	0.7400 (3)	0.0196 (5)	0.75
C2'	−0.0657 (5)	0.45332 (12)	0.7124 (3)	0.0234 (6)	0.75
H2'	−0.2039	0.4633	0.6508	0.028*	0.75
C3'	−0.0577 (7)	0.39612 (15)	0.7741 (4)	0.0249 (7)	0.75
H3'	−0.1910	0.3674	0.7547	0.030*	0.75
C4'	0.1426 (10)	0.38073 (15)	0.8633 (5)	0.0240 (10)	0.75
H4'	0.1478	0.3416	0.9053	0.029*	0.75
C5'	0.3357 (8)	0.42287 (16)	0.8910 (4)	0.0270 (8)	0.75
H5'	0.4744	0.4127	0.9521	0.032*	0.75
C6'	0.3273 (6)	0.47996 (12)	0.8296 (3)	0.0252 (6)	0.75
H6'	0.4607	0.5086	0.8489	0.030*	0.75
C2A	0.2379 (12)	0.5677 (3)	0.7425 (6)	0.0136 (12)*	0.25
H2A	0.3774	0.5825	0.8067	0.016*	0.25
C1A'	0.2028 (15)	0.5022 (3)	0.7822 (7)	0.0148 (18)*	0.25
C2A'	−0.0070 (14)	0.4687 (4)	0.7323 (8)	0.023 (2)*	0.25
H2A'	−0.1319	0.4876	0.6734	0.028*	0.25
C3A'	−0.034 (2)	0.4077 (4)	0.7686 (13)	0.029 (2)*	0.25
H3A'	−0.1773	0.3848	0.7346	0.034*	0.25
C4A'	0.149 (3)	0.3801 (3)	0.8548 (16)	0.025 (3)*	0.25
H4A'	0.1304	0.3384	0.8796	0.030*	0.25
C5A'	0.359 (2)	0.4136 (4)	0.9047 (12)	0.023 (2)*	0.25
H5A'	0.4834	0.3947	0.9636	0.028*	0.25
C6A'	0.3855 (13)	0.4746 (4)	0.8683 (7)	0.023 (2)*	0.25
H6A'	0.5289	0.4975	0.9024	0.028*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0313 (7)	0.0187 (6)	0.0318 (7)	0.0028 (5)	0.0160 (5)	0.0042 (5)
O2	0.0254 (6)	0.0210 (7)	0.0292 (6)	0.0049 (5)	0.0106 (5)	−0.0001 (5)
O3	0.0260 (6)	0.0193 (6)	0.0270 (6)	−0.0016 (5)	0.0116 (5)	0.0034 (5)
C3	0.0280 (10)	0.0224 (10)	0.0300 (10)	0.0014 (8)	0.0126 (7)	0.0005 (8)
C4	0.0192 (9)	0.0201 (9)	0.0195 (9)	0.0008 (8)	0.0030 (7)	−0.0010 (7)
C5	0.0213 (9)	0.0162 (9)	0.0229 (9)	0.0032 (7)	0.0042 (7)	−0.0018 (7)
C6	0.0203 (9)	0.0184 (9)	0.0176 (9)	−0.0007 (7)	0.0016 (7)	0.0021 (7)
C7	0.0208 (9)	0.0241 (9)	0.0196 (9)	−0.0008 (7)	0.0065 (7)	−0.0021 (8)
C8	0.0229 (9)	0.0184 (9)	0.0258 (9)	0.0057 (7)	0.0082 (7)	−0.0017 (8)
C9	0.0202 (8)	0.0173 (8)	0.0190 (9)	−0.0001 (7)	0.0039 (7)	0.0008 (7)
C10	0.0168 (8)	0.0195 (9)	0.0179 (8)	0.0006 (7)	0.0030 (6)	−0.0014 (7)
C2	0.0195 (12)	0.0228 (12)	0.0303 (13)	−0.0011 (10)	0.0072 (10)	0.0006 (10)
C1'	0.0188 (13)	0.0185 (12)	0.0223 (13)	0.0007 (11)	0.0070 (10)	−0.0011 (10)
C2'	0.0215 (13)	0.0232 (15)	0.0260 (14)	0.0014 (12)	0.0049 (10)	0.0005 (12)
C3'	0.0229 (14)	0.0206 (15)	0.0321 (15)	−0.0038 (12)	0.0095 (11)	0.0024 (13)
C4'	0.0304 (15)	0.0176 (14)	0.0254 (16)	−0.0011 (10)	0.0129 (11)	0.0022 (10)
C5'	0.0264 (15)	0.0262 (18)	0.0282 (17)	0.0043 (13)	−0.0001 (11)	−0.0018 (12)
C6'	0.0250 (14)	0.0216 (13)	0.0295 (16)	−0.0078 (13)	0.0041 (13)	−0.0034 (13)

Geometric parameters (Å, º)

O1—C9	1.3812 (17)	C2—H2	1.0000
O1—C2A	1.408 (6)	C1'—C2'	1.381 (4)
O1—C2	1.423 (2)	C1'—C6'	1.390 (4)
O2—C4	1.2249 (17)	C2'—C3'	1.392 (4)
O3—C6	1.3687 (18)	C2'—H2'	0.9500
O3—H3H	0.9580	C3'—C4'	1.382 (3)
C3—C2A	1.432 (6)	C3'—H3'	0.9500
C3—C2	1.499 (3)	C4'—C5'	1.384 (3)
C3—C4	1.504 (2)	C4'—H4'	0.9500
C3—H3A	0.9900	C5'—C6'	1.389 (4)
C3—H3B	0.9900	C5'—H5'	0.9500
C3—H3C	0.9600	C6'—H6'	0.9500
C3—H3D	0.9600	C2A—C1A'	1.497 (8)
C4—C10	1.474 (2)	C2A—H2A	1.0000
C5—C6	1.378 (2)	C1A'—C2A'	1.3900
C5—C10	1.406 (2)	C1A'—C6A'	1.3900
C5—H5A	0.9500	C2A'—C3A'	1.3900
C6—C7	1.399 (2)	C2A'—H2A'	0.9500
C7—C8	1.379 (2)	C3A'—C4A'	1.3900
C7—H7A	0.9500	C3A'—H3A'	0.9500
C8—C9	1.393 (2)	C4A'—C5A'	1.3900
C8—H8A	0.9500	C4A'—H4A'	0.9500
C9—C10	1.395 (2)	C5A'—C6A'	1.3900
C2—C1'	1.511 (3)	C5A'—H5A'	0.9500
C2—H3C	1.5327	C6A'—H6A'	0.9500
C9—O1—C2A	115.6 (3)	C3—C2—H2	107.0
C9—O1—C2	116.10 (14)	C1'—C2—H2	107.0
C6—O3—H3H	111.0	C2'—C1'—C6'	118.9 (2)
C2A—C3—C4	116.2 (3)	C2'—C1'—C2	119.8 (2)
C2—C3—C4	113.64 (14)	C6'—C1'—C2	121.2 (2)
C2—C3—H3A	108.8	C1'—C2'—C3'	120.5 (2)
C4—C3—H3A	108.8	C1'—C2'—H2'	119.8
C2A—C3—H3B	132.0	C3'—C2'—H2'	119.8
C2—C3—H3B	108.8	C4'—C3'—C2'	120.5 (3)
C4—C3—H3B	108.8	C4'—C3'—H3'	119.7
H3A—C3—H3B	107.7	C2'—C3'—H3'	119.7
C2A—C3—H3C	107.4	C3'—C4'—C5'	119.3 (3)
C4—C3—H3C	108.5	C3'—C4'—H4'	120.4
H3A—C3—H3C	137.4	C5'—C4'—H4'	120.4
C2A—C3—H3D	108.6	C6'—C5'—C4'	120.2 (3)
C2—C3—H3D	135.2	C6'—C5'—H5'	119.9
C4—C3—H3D	108.4	C4'—C5'—H5'	119.9
H3C—C3—H3D	107.5	C5'—C6'—C1'	120.7 (2)
O2—C4—C10	122.60 (14)	C5'—C6'—H6'	119.7
O2—C4—C3	122.14 (14)	C1'—C6'—H6'	119.7
C10—C4—C3	115.26 (13)	O1—C2A—C3	118.4 (4)
C6—C5—C10	120.54 (14)	O1—C2A—C1A'	108.9 (5)
C6—C5—H5A	119.7	C3—C2A—C1A'	116.7 (5)
C10—C5—H5A	119.7	O1—C2A—H2A	103.6
O3—C6—C5	119.14 (14)	C3—C2A—H2A	103.6
O3—C6—C7	121.44 (14)	C1A'—C2A—H2A	103.6
C5—C6—C7	119.42 (15)	C2A'—C1A'—C6A'	120.0
C8—C7—C6	120.73 (15)	C2A'—C1A'—C2A	120.9 (6)
C8—C7—H7A	119.6	C6A'—C1A'—C2A	119.1 (6)
C6—C7—H7A	119.6	C3A'—C2A'—C1A'	120.0
C7—C8—C9	119.94 (15)	C3A'—C2A'—H2A'	120.0
C7—C8—H8A	120.0	C1A'—C2A'—H2A'	120.0
C9—C8—H8A	120.0	C2A'—C3A'—C4A'	120.0
O1—C9—C8	117.06 (14)	C2A'—C3A'—H3A'	120.0
O1—C9—C10	122.89 (14)	C4A'—C3A'—H3A'	120.0
C8—C9—C10	120.05 (14)	C5A'—C4A'—C3A'	120.0
C9—C10—C5	119.31 (14)	C5A'—C4A'—H4A'	120.0
C9—C10—C4	120.05 (14)	C3A'—C4A'—H4A'	120.0
C5—C10—C4	120.63 (14)	C4A'—C5A'—C6A'	120.0
O1—C2—C3	113.13 (16)	C4A'—C5A'—H5A'	120.0
O1—C2—C1'	107.87 (17)	C6A'—C5A'—H5A'	120.0
C3—C2—C1'	114.39 (18)	C5A'—C6A'—C1A'	120.0
O1—C2—H3C	143.4	C5A'—C6A'—H6A'	120.0
C1'—C2—H3C	105.7	C1A'—C6A'—H6A'	120.0
O1—C2—H2	107.0
C2A—C3—C4—O2	−164.7 (3)	O1—C2—C1'—C2'	−130.0 (2)
C2—C3—C4—O2	153.73 (16)	C3—C2—C1'—C2'	103.2 (3)
C2A—C3—C4—C10	14.4 (4)	O1—C2—C1'—C6'	50.9 (3)
C2—C3—C4—C10	−27.2 (2)	C3—C2—C1'—C6'	−75.9 (3)
C10—C5—C6—O3	−179.48 (13)	C6'—C1'—C2'—C3'	0.5 (3)
C10—C5—C6—C7	0.8 (2)	C2—C1'—C2'—C3'	−178.7 (3)
O3—C6—C7—C8	−179.99 (14)	C1'—C2'—C3'—C4'	−0.4 (3)
C5—C6—C7—C8	−0.3 (2)	C2'—C3'—C4'—C5'	0.1 (3)
C6—C7—C8—C9	−0.6 (2)	C3'—C4'—C5'—C6'	0.1 (3)
C2A—O1—C9—C8	158.0 (3)	C4'—C5'—C6'—C1'	0.1 (3)
C2—O1—C9—C8	−158.30 (16)	C2'—C1'—C6'—C5'	−0.4 (3)
C2A—O1—C9—C10	−21.2 (4)	C2—C1'—C6'—C5'	178.8 (3)
C2—O1—C9—C10	22.5 (2)	C9—O1—C2A—C3	40.1 (6)
C7—C8—C9—O1	−178.24 (13)	C2—O1—C2A—C3	−60.5 (4)
C7—C8—C9—C10	1.0 (2)	C9—O1—C2A—C1A'	176.5 (4)
O1—C9—C10—C5	178.71 (13)	C2—O1—C2A—C1A'	75.9 (5)
C8—C9—C10—C5	−0.5 (2)	C2—C3—C2A—O1	58.6 (4)
O1—C9—C10—C4	−0.1 (2)	C4—C3—C2A—O1	−36.8 (6)
C8—C9—C10—C4	−179.34 (14)	C2—C3—C2A—C1A'	−74.5 (6)
C6—C5—C10—C9	−0.4 (2)	C4—C3—C2A—C1A'	−169.9 (4)
C6—C5—C10—C4	178.44 (14)	O1—C2A—C1A'—C2A'	−82.3 (7)
O2—C4—C10—C9	−177.51 (14)	C3—C2A—C1A'—C2A'	54.9 (8)
C3—C4—C10—C9	3.4 (2)	O1—C2A—C1A'—C6A'	96.7 (7)
O2—C4—C10—C5	3.7 (2)	C3—C2A—C1A'—C6A'	−126.1 (6)
C3—C4—C10—C5	−175.46 (14)	C6A'—C1A'—C2A'—C3A'	0.0
C9—O1—C2—C3	−46.5 (2)	C2A—C1A'—C2A'—C3A'	178.9 (8)
C2A—O1—C2—C3	52.7 (4)	C1A'—C2A'—C3A'—C4A'	0.0
C9—O1—C2—C1'	−174.09 (17)	C2A'—C3A'—C4A'—C5A'	0.0
C2A—O1—C2—C1'	−74.8 (4)	C3A'—C4A'—C5A'—C6A'	0.0
C2A—C3—C2—O1	−53.9 (4)	C4A'—C5A'—C6A'—C1A'	0.0
C4—C3—C2—O1	48.9 (2)	C2A'—C1A'—C6A'—C5A'	0.0
C2A—C3—C2—C1'	70.2 (4)	C2A—C1A'—C6A'—C5A'	−179.0 (8)
C4—C3—C2—C1'	172.97 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3H···O2^i	0.96	1.80	2.7553 (17)	172.7

Symmetry code: (i) x+1, −y+3/2, z−1/2.