Structural analysis and multipole modelling of quercetin monohydrate – a quantitative and comparative study

The multipolar atom model, constructed by transferring the charge-density parameters from an experimental or theoretical database, is considered to be an easy replacement of the widely used independent atom model. The present study on a new crystal structure of quercetin monohydrate [2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one monohydrate], a plant flavonoid, determined by X-ray diffraction, demonstrates that the transferred multipolar atom model approach greatly improves several factors: the accuracy of atomic positions and the magnitudes of atomic displacement parameters, the residual electron densities and the crystallographic figures of merit. The charge-density features, topological analysis and electrostatic interaction energies obtained from the multipole models based on experimental database transfer and periodic quantum mechanical calculations are found to compare well. This quantitative and comparative study shows that in the absence of high-resolution diffraction data, the database transfer approach can be applied to the multipolar electron density features very accurately.

Computing details

For all structures, data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36); cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36); data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36); program(s) used to solve structure: SHELXL97; program(s) used to refine structure: MoPro (J. Appl. Cryst. 2005, 38, 38-54); molecular graphics: MoPro (J. Appl. Cryst. 2005, 38, 38-54); software used to prepare material for publication: MoPro (J. Appl. Cryst. 2005, 38, 38-54).

2(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one monohydrate (IAM_R)

Crystal data

C15H10O7·H2O	F(000) = 664
Mr = 320.24	Dx = 1.672 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 15541 reflections
a = 8.737 (1) Å	θ = 5.1–76.3°
b = 4.852 (1) Å	µ = 0.14 mm^−1
c = 30.160 (1) Å	T = 110 K
β = 95.52 (1)°	, yellow
V = 1272.6 (3) Å^3	0.35 × 0.19 × 0.16 mm
Z = 4

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	2652 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2565 reflections with > 2.0σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 10.4508 pixels mm^-1	θmax = 76.3°, θmin = 5.1°
ω scans	h = −11→10
Absorption correction: multi-scan 'Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'	k = 0→6
Tmin = 0.672, Tmax = 1.000	l = 0→37
69706 measured reflections

Refinement

Refinement on F	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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 2.19	w = 1/[3.68*σ^2(Fo^2) + 0.001*Yo^2]
2652 reflections	(Δ/^σ)max < 0.001
256 parameters	Δ^ρmax = 0.39 e Å−3
29 restraints	Δ^ρmin =^−0.24 e Å−3

Special details

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27–08-2009 CrysAlis171. NET) (compiled Aug 27 2009,17:19:36)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O13	0.8862 (1)	1.3941 (2)	0.13774 (3)	0.0180 (3)
H13	0.87238	1.36317	0.10595	0.02696*
O4	0.3500 (1)	0.4013 (2)	0.02118 (3)	0.0194 (3)
O1	0.4277 (1)	0.4791 (2)	0.15585 (3)	0.0149 (2)
O7	0.0842 (1)	−0.2282 (2)	0.18251 (3)	0.0173 (3)
H7	0.01524	−0.35998	0.16710	0.02603*
O5	0.1485 (1)	0.0174 (2)	0.03260 (3)	0.0219 (3)
H5	0.21707	0.14063	0.01890	0.03260*
O14	0.9106 (1)	1.3765 (2)	0.22600 (3)	0.0191 (3)
H14	0.91184	1.33948	0.25753	0.02850*
O3	0.5503 (1)	0.7861 (2)	0.05557 (3)	0.0219 (3)
H3	0.53059	0.71546	0.02560	0.03287*
O1W	0.8684 (1)	0.3663 (3)	0.04755 (3)	0.0275 (3)
H1W	0.92960	0.24275	0.03134	0.04093*
H2W	0.79359	0.43369	0.02437	0.04093*
C10	0.2939 (1)	0.2526 (3)	0.09277 (4)	0.0146 (3)
C2	0.5048 (1)	0.6462 (3)	0.12888 (4)	0.0145 (3)
C8	0.2556 (1)	0.1239 (3)	0.16907 (4)	0.0155 (3)
H8	0.28052	0.14895	0.20467	0.01849*
C9	0.3251 (1)	0.2851 (3)	0.13890 (4)	0.0140 (3)
C6	0.1125 (1)	−0.1104 (3)	0.10634 (4)	0.0162 (3)
H6	0.02851	−0.26208	0.09381	0.01939*
C11	0.6075 (1)	0.8395 (3)	0.15433 (4)	0.0147 (3)
C7	0.1496 (1)	−0.0724 (3)	0.15230 (4)	0.0150 (3)
C3	0.4790 (1)	0.6200 (3)	0.08340 (4)	0.0160 (3)
C4	0.3723 (1)	0.4215 (3)	0.06347 (4)	0.0157 (4)
C12	0.6987 (1)	1.0277 (3)	0.13288 (4)	0.0151 (3)
H12	0.69547	1.02737	0.09694	0.01794*
C13	0.7962 (1)	1.2075 (3)	0.15739 (4)	0.0150 (3)
C14	0.8073 (1)	1.2034 (3)	0.20396 (4)	0.0155 (3)
C5	0.1844 (1)	0.0502 (3)	0.07718 (4)	0.0158 (4)
C16	0.6162 (2)	0.8414 (3)	0.20101 (4)	0.0170 (4)
H16	0.54952	0.69230	0.21758	0.02019*
C15	0.7147 (2)	1.0239 (3)	0.22524 (4)	0.0176 (4)
H15	0.72023	1.02763	0.26123	0.02068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0202 (5)	0.0181 (5)	0.0155 (4)	−0.0071 (4)	0.0030 (4)	−0.0003 (4)
O4	0.0226 (5)	0.0236 (6)	0.0120 (4)	−0.0049 (4)	0.0023 (3)	−0.0006 (4)
O1	0.0160 (4)	0.0148 (5)	0.0139 (4)	−0.0041 (3)	0.0012 (3)	−0.0001 (4)
O7	0.0194 (5)	0.0174 (5)	0.0152 (4)	−0.0056 (4)	0.0029 (3)	0.0013 (4)
O5	0.0263 (5)	0.0263 (6)	0.0128 (5)	−0.0101 (4)	0.0004 (4)	−0.0024 (4)
O14	0.0210 (5)	0.0204 (5)	0.0156 (4)	−0.0071 (4)	−0.0006 (4)	−0.0003 (4)
O3	0.0281 (5)	0.0249 (6)	0.0129 (4)	−0.0113 (4)	0.0047 (4)	−0.0008 (4)
O1W	0.0304 (6)	0.0349 (7)	0.0165 (5)	0.0046 (5)	−0.0012 (4)	−0.0012 (4)
C10	0.0144 (6)	0.0146 (7)	0.0147 (6)	−0.0001 (5)	0.0019 (5)	−0.0004 (5)
C2	0.0141 (6)	0.0133 (7)	0.0162 (6)	−0.0003 (5)	0.0026 (4)	0.0007 (5)
C8	0.0169 (6)	0.0159 (7)	0.0137 (6)	0.0006 (5)	0.0018 (5)	0.0000 (5)
C9	0.0137 (6)	0.0125 (7)	0.0156 (6)	−0.0001 (5)	0.0005 (4)	−0.0021 (5)
C6	0.0157 (6)	0.0151 (7)	0.0177 (6)	−0.0019 (5)	0.0019 (5)	−0.0020 (5)
C11	0.0138 (6)	0.0136 (7)	0.0166 (6)	−0.0004 (5)	0.0008 (5)	−0.0007 (5)
C7	0.0139 (6)	0.0144 (7)	0.0167 (6)	0.0014 (5)	0.0030 (5)	0.0016 (5)
C3	0.0165 (6)	0.0152 (7)	0.0164 (6)	−0.0025 (5)	0.0042 (5)	0.0006 (5)
C4	0.0162 (6)	0.0171 (7)	0.0137 (6)	0.0007 (5)	0.0017 (5)	−0.0009 (5)
C12	0.0150 (6)	0.0155 (7)	0.0147 (6)	0.0007 (5)	0.0012 (5)	0.0005 (5)
C13	0.0140 (6)	0.0133 (7)	0.0176 (6)	−0.0005 (5)	0.0032 (4)	0.0018 (5)
C14	0.0151 (6)	0.0139 (7)	0.0171 (6)	0.0000 (5)	−0.0005 (5)	−0.0009 (5)
C5	0.0166 (6)	0.0173 (7)	0.0133 (6)	0.0003 (5)	0.0008 (5)	−0.0020 (5)
C16	0.0172 (6)	0.0166 (7)	0.0170 (6)	−0.0020 (5)	0.0016 (5)	0.0013 (5)
C15	0.0188 (6)	0.0185 (7)	0.0153 (6)	−0.0022 (5)	0.0009 (5)	0.0004 (5)

Geometric parameters (Å, º)

O13—C13	1.371 (2)	C2—C3	1.374 (2)
O13—H13	0.966	C2—C11	1.464 (2)
O4—C4	1.275 (2)	C8—C9	1.384 (2)
O1—C9	1.365 (2)	C8—C7	1.390 (2)
O1—C2	1.371 (2)	C8—H8	1.082
O7—C7	1.353 (2)	C6—C5	1.372 (2)
O7—H7	0.966	C6—C7	1.405 (2)
O5—C5	1.360 (2)	C6—H6	1.081
O5—H5	0.967	C11—C16	1.403 (2)
O14—C14	1.358 (2)	C11—C12	1.409 (2)
O14—H14	0.967	C3—C4	1.432 (2)
O3—C3	1.358 (2)	C12—C13	1.383 (2)
O3—H3	0.966	C12—H12	1.082
O1W—H2W	0.967	C13—C14	1.399 (2)
O1W—H1W	0.967	C14—C15	1.388 (2)
C10—C9	1.401 (2)	C16—C15	1.391 (2)
C10—C5	1.419 (2)	C16—H16	1.081
C10—C4	1.428 (2)	C15—H15	1.082
O13—C13—C14	117.1 (1)	C2—C3—C4	121.3 (1)
O13—C13—C12	122.4 (1)	C2—C11—C16	120.1 (1)
H13—O13—C13	107.7	C2—C11—C12	121.3 (1)
O4—C4—C3	120.2 (1)	C8—C7—C6	122.1 (2)
O4—C4—C10	122.6 (1)	H8—C8—C9	122.0
O1—C9—C10	120.5 (1)	H8—C8—C7	120.1
O1—C9—C8	117.2 (1)	C9—C10—C5	117.9 (1)
O1—C2—C3	119.7 (2)	C9—C10—C4	119.4 (2)
O1—C2—C11	112.3 (1)	C9—C8—C7	117.8 (2)
O7—C7—C8	116.6 (1)	H6—C6—C5	120.0
O7—C7—C6	121.2 (2)	H6—C6—C7	121.2
H7—O7—C7	109.3	C11—C2—C3	128.0 (2)
O5—C5—C10	119.5 (1)	C11—C16—C15	120.2 (1)
O5—C5—C6	119.4 (1)	C11—C16—H16	118.7
H5—O5—C5	104.9	C11—C12—C13	120.7 (1)
O14—C14—C13	117.5 (1)	C11—C12—H12	119.9
O14—C14—C15	123.4 (2)	C7—C6—C5	118.8 (2)
H14—O14—C14	108.1	C4—C10—C5	122.7 (2)
O3—C3—C2	121.4 (1)	C12—C13—C14	120.5 (1)
O3—C3—C4	117.3 (1)	C12—C11—C16	118.6 (1)
H3—O3—C3	108.4	H12—C12—C13	119.4
H1W—O1W—H2W	102.3	C13—C14—C15	119.1 (1)
C10—C9—C8	122.3 (1)	C14—C15—C16	121.0 (2)
C10—C5—C6	121.1 (2)	C14—C15—H15	118.8
C10—C4—C3	117.3 (1)	C16—C15—H15	120.2
C2—O1—C9	121.9 (1)	H16—C16—C15	121.1
O13—C13—C14—O14	−2.5 (1)	C10—C9—O1—C2	−0.7 (1)
O13—C13—C14—C15	178.0 (1)	C10—C9—C8—C7	−1.2 (1)
O13—C13—C12—C11	−179.8 (1)	C10—C9—C8—H8	179.7
O13—C13—C12—H12	2.3	C10—C5—C6—C7	−0.3 (1)
H13—O13—C13—C14	175.6	C10—C5—C6—H6	179.3
H13—O13—C13—C12	−3.9	C10—C4—C3—C2	0.09 (12)
O4—C4—C3—O3	1.7 (1)	C2—O1—C9—C8	178.84 (10)
O4—C4—C3—C2	179.9 (1)	C2—C11—C16—C15	179.5 (1)
O4—C4—C10—C9	179.5 (1)	C2—C11—C16—H16	2.5
O4—C4—C10—C5	−0.4 (1)	C2—C11—C12—C13	−179.4 (1)
O1—C9—C10—C5	−179.1 (1)	C2—C11—C12—H12	−1.5
O1—C9—C10—C4	1.0 (1)	C8—C9—C10—C5	1.4 (1)
O1—C9—C8—C7	179.3 (1)	C8—C9—C10—C4	−178.5 (1)
O1—C9—C8—H8	0.1	C8—C7—C6—C5	0.6 (1)
O1—C2—C3—O3	178.37 (10)	C8—C7—C6—H6	−179.1
O1—C2—C3—C4	0.2 (1)	H8—C8—C7—C6	179.4
O1—C2—C11—C16	−1.0 (1)	C9—O1—C2—C3	0.11 (11)
O1—C2—C11—C12	179.3 (1)	C9—O1—C2—C11	179.5 (1)
O7—C7—C8—C9	179.6 (1)	C9—C10—C5—C6	−0.6 (1)
O7—C7—C8—H8	−1.2	C9—C10—C4—C3	−0.7 (1)
O7—C7—C6—C5	−178.8 (1)	C9—C8—C7—C6	0.2 (1)
O7—C7—C6—H6	1.5	C6—C5—C10—C4	179.3 (1)
H7—O7—C7—C8	−178.3	C11—C2—C3—C4	−179.1 (1)
H7—O7—C7—C6	1.1	C11—C16—C15—C14	−1.0 (1)
O5—C5—C10—C9	178.5 (1)	C11—C16—C15—H15	179.1
O5—C5—C10—C4	−1.7 (1)	C11—C12—C13—C14	0.8 (1)
O5—C5—C6—C7	−179.4 (1)	C3—C2—C11—C16	178.3 (1)
O5—C5—C6—H6	0.3	C3—C2—C11—C12	−1.3 (1)
H5—O5—C5—C10	4.7	C3—C4—C10—C5	179.4 (1)
H5—O5—C5—C6	−176.2	C12—C13—C14—C15	−2.5 (1)
O14—C14—C13—C12	177.0 (1)	C12—C11—C16—C15	−0.8 (1)
O14—C14—C15—C16	−176.8 (1)	C12—C11—C16—H16	−177.8
O14—C14—C15—H15	3.1	H12—C12—C13—C14	−177.2
H14—O14—C14—C13	−175.0	H12—C12—C11—C16	178.9
H14—O14—C14—C15	4.4	C13—C14—C15—C16	2.7 (1)
O3—C3—C2—C11	−0.9 (1)	C13—C14—C15—H15	−177.4
O3—C3—C4—C10	−178.1 (1)	C13—C12—C11—C16	0.9 (1)
H3—O3—C3—C2	170.5	C14—C15—C16—H16	175.9
H3—O3—C3—C4	−11.3	H16—C16—C15—H15	−4.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O13^i	0.97	1.81	2.779 (1)	180
O7—H7···O14^i	0.97	2.44	2.843 (1)	105
O5—H5···O4	0.97	1.71	2.608 (1)	152
O5—H5···C4	0.97	2.27	2.861 (2)	119
O3—H3···O4	0.97	2.19	2.697 (1)	112
C12—H12···O3	1.08	2.06	2.812 (2)	124
O13—H13···O1W^ii	0.97	1.76	2.713 (1)	169
O1W—H1W···O5^iii	0.97	2.20	3.045 (2)	145
O1W—H1W···O5^iv	0.97	2.35	3.043 (1)	128
O3—H3···O4^v	0.97	1.92	2.708 (1)	137
O1W—H2W···O4^v	0.97	1.94	2.906 (1)	175
O14—H14···O7^vi	0.97	1.84	2.802 (1)	179

Symmetry codes: (i) x−1, y−2, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z; (vi) −x+1, y+3/2, −z+1/2.

2(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one monohydrate (TAAM_R)

Crystal data

C15H10O7·H2O	F(000) = 664
Mr = 320.24	Dx = 1.672 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 15541 reflections
a = 8.737 (1) Å	θ = 5.1–76.3°
b = 4.852 (1) Å	µ = 0.14 mm^−1
c = 30.160 (1) Å	T = 110 K
β = 95.52 (1)°	, yellow
V = 1272.6 (3) Å^3	0.35 × 0.19 × 0.16 mm
Z = 4

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	2652 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2565 reflections with > 2.0σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 10.4508 pixels mm^-1	θmax = 76.3°, θmin = 5.1°
ω scans	h = −11→10
Absorption correction: multi-scan 'Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'	k = 0→6
Tmin = 0.672, Tmax = 1.000	l = 0→37
69706 measured reflections

Refinement

Refinement on F	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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.028	H-atom parameters constrained
S = 1.11	w = 1/[3.68*σ^2(Fo^2) + 0.001*Yo^2]
2652 reflections	(Δ/^σ)max = 0.001
256 parameters	Δ^ρmax = 0.14 e Å−3
29 restraints	Δ^ρmin =^−0.16 e Å−3

Special details

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27–08-2009 CrysAlis171. NET) (compiled Aug 27 2009,17:19:36)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O13	0.88599 (5)	1.3936 (1)	0.13768 (2)	0.0152 (1)
H13	0.86918	1.36825	0.10578	0.02282*
O4	0.35000 (6)	0.4012 (1)	0.02120 (2)	0.0169 (1)
O1	0.42748 (5)	0.4792 (1)	0.15574 (2)	0.0125 (1)
O7	0.08417 (5)	−0.2284 (1)	0.18247 (2)	0.0149 (1)
H7	0.01450	−0.36211	0.16786	0.02240*
O5	0.14876 (6)	0.0175 (1)	0.03267 (2)	0.0190 (1)
H5	0.21370	0.14674	0.01881	0.02841*
O14	0.91044 (5)	1.3763 (1)	0.22603 (2)	0.0165 (1)
H14	0.91306	1.33213	0.25736	0.02459*
O3	0.55024 (6)	0.7854 (1)	0.05548 (2)	0.0192 (1)
H3	0.53348	0.70411	0.02614	0.02887*
O1W	0.86825 (6)	0.3664 (1)	0.04754 (2)	0.0249 (2)
H1W	0.93040	0.24759	0.03076	0.03726*
H2W	0.78945	0.42970	0.02513	0.03719*
C10	0.29383 (7)	0.2530 (1)	0.09283 (2)	0.0121 (2)
C2	0.50453 (7)	0.6458 (1)	0.12889 (2)	0.0119 (2)
C8	0.25570 (7)	0.1235 (1)	0.16917 (2)	0.0127 (2)
H8	0.28383	0.14527	0.20474	0.01529*
C9	0.32559 (7)	0.2857 (1)	0.13891 (2)	0.0113 (2)
C6	0.11207 (8)	−0.1109 (1)	0.10636 (2)	0.0134 (2)
H6	0.02892	−0.26471	0.09399	0.01616*
C11	0.60748 (7)	0.8393 (1)	0.15426 (2)	0.0121 (2)
C7	0.14945 (7)	−0.0732 (1)	0.15241 (2)	0.0123 (2)
C3	0.47918 (8)	0.6203 (1)	0.08332 (2)	0.0134 (2)
C4	0.37211 (7)	0.4214 (1)	0.06348 (2)	0.0130 (2)
C12	0.69859 (7)	1.0275 (1)	0.13281 (2)	0.0127 (2)
H12	0.69401	1.02917	0.09681	0.01522*
C13	0.79638 (7)	1.2080 (1)	0.15733 (2)	0.0124 (2)
C14	0.80768 (7)	1.2040 (1)	0.20404 (2)	0.0131 (2)
C5	0.18439 (7)	0.0505 (1)	0.07699 (2)	0.0134 (2)
C16	0.61611 (8)	0.8416 (2)	0.20099 (2)	0.0145 (2)
H16	0.54607	0.69940	0.21794	0.01738*
C15	0.71447 (8)	1.0236 (2)	0.22533 (2)	0.0148 (2)
H15	0.71964	1.03238	0.26133	0.01773*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0171 (2)	0.0158 (3)	0.0126 (2)	−0.0057 (2)	0.0021 (2)	−0.0004 (2)
O4	0.0199 (3)	0.0211 (3)	0.0097 (2)	−0.0065 (2)	0.0017 (2)	−0.0008 (2)
O1	0.0140 (2)	0.0127 (2)	0.0107 (2)	−0.0035 (2)	0.0008 (2)	−0.00013 (17)
O7	0.0170 (2)	0.0148 (3)	0.0129 (2)	−0.0049 (2)	0.0020 (2)	0.0008 (2)
O5	0.0225 (3)	0.0228 (3)	0.0116 (2)	−0.0093 (2)	0.0005 (2)	−0.0021 (2)
O14	0.0185 (2)	0.0175 (3)	0.0132 (2)	−0.0067 (2)	−0.0002 (2)	−0.00015 (19)
O3	0.0244 (3)	0.0214 (3)	0.0120 (2)	−0.0108 (2)	0.0045 (2)	−0.0012 (2)
O1W	0.0281 (3)	0.0320 (3)	0.0141 (2)	0.0042 (2)	−0.0016 (2)	−0.0017 (2)
C10	0.0128 (3)	0.0125 (3)	0.0107 (3)	−0.0026 (2)	0.0009 (2)	−0.0005 (2)
C2	0.0123 (3)	0.0119 (3)	0.0113 (3)	−0.0022 (2)	0.0014 (2)	−0.0006 (2)
C8	0.0146 (3)	0.0134 (3)	0.0100 (3)	−0.0032 (2)	0.0014 (2)	0.0001 (2)
C9	0.0122 (3)	0.0110 (3)	0.0106 (3)	−0.0016 (2)	0.0008 (2)	−0.0006 (2)
C6	0.0142 (3)	0.0138 (3)	0.0122 (3)	−0.0042 (2)	0.0013 (2)	−0.0012 (2)
C11	0.0124 (3)	0.0124 (3)	0.0113 (3)	−0.0028 (2)	0.0008 (2)	−0.0003 (2)
C7	0.0123 (3)	0.0124 (3)	0.0122 (3)	−0.0013 (2)	0.0015 (2)	0.0002 (2)
C3	0.0148 (3)	0.0143 (4)	0.0110 (3)	−0.0044 (2)	0.0019 (2)	−0.0013 (2)
C4	0.0146 (3)	0.0151 (4)	0.0093 (3)	−0.0026 (2)	0.0012 (2)	−0.0008 (2)
C12	0.0130 (3)	0.0130 (3)	0.0119 (3)	−0.0035 (2)	0.0011 (2)	0.0002 (2)
C13	0.0129 (3)	0.0124 (3)	0.0119 (3)	−0.0026 (2)	0.0010 (2)	0.0001 (2)
C14	0.0140 (3)	0.0131 (3)	0.0118 (3)	−0.0022 (2)	0.0004 (2)	0.0004 (2)
C5	0.0141 (3)	0.0140 (4)	0.0120 (3)	−0.0033 (2)	0.0012 (2)	−0.0012 (2)
C16	0.0163 (3)	0.0152 (4)	0.0117 (3)	−0.0047 (2)	0.0009 (2)	0.0003 (3)
C15	0.0173 (3)	0.0160 (4)	0.0110 (3)	−0.0055 (3)	0.0010 (2)	0.0002 (3)

Geometric parameters (Å, º)

O13—C13	1.3656 (8)	C2—C3	1.3766 (9)
O13—H13	0.967	C2—C11	1.4640 (10)
O4—C4	1.2752 (9)	C8—C9	1.3900 (10)
O1—C9	1.3582 (9)	C8—C7	1.3922 (10)
O1—C2	1.3666 (8)	C8—H8	1.082
O7—C7	1.3466 (9)	C6—C5	1.3800 (10)
O7—H7	0.967	C6—C7	1.4078 (9)
O5—C5	1.3524 (9)	C6—H6	1.083
O5—H5	0.967	C11—C16	1.4044 (9)
O14—C14	1.3529 (9)	C11—C12	1.4088 (10)
O14—H14	0.967	C3—C4	1.4341 (10)
O3—C3	1.3534 (9)	C12—C13	1.3865 (10)
O3—H3	0.967	C12—H12	1.083
O1W—H2W	0.967	C13—C14	1.4028 (10)
O1W—H1W	0.967	C14—C15	1.3937 (10)
C10—C9	1.3999 (9)	C16—C15	1.3912 (10)
C10—C5	1.4214 (10)	C16—H16	1.083
C10—C4	1.4267 (10)	C15—H15	1.083
O13—C13—C14	117.20 (6)	C2—C3—C4	120.86 (7)
O13—C13—C12	122.32 (8)	C2—C11—C16	120.04 (6)
H13—O13—C13	108.0	C2—C11—C12	121.44 (6)
O4—C4—C3	119.94 (6)	C8—C7—C6	122.04 (8)
O4—C4—C10	122.74 (6)	H8—C8—C9	121.6
O1—C9—C10	120.64 (7)	H8—C8—C7	120.4
O1—C9—C8	117.34 (7)	C9—C10—C5	118.34 (7)
O1—C2—C3	119.83 (8)	C9—C10—C4	119.34 (8)
O1—C2—C11	112.50 (5)	C9—C8—C7	118.00 (8)
O7—C7—C8	116.72 (6)	H6—C6—C5	120.2
O7—C7—C6	121.24 (8)	H6—C6—C7	120.9
H7—O7—C7	110.9	C11—C2—C3	127.67 (8)
O5—C5—C10	119.82 (6)	C11—C16—C15	120.36 (7)
O5—C5—C6	119.42 (6)	C11—C16—H16	119.4
H5—O5—C5	105.2	C11—C12—C13	120.72 (6)
O14—C14—C13	117.59 (7)	C11—C12—H12	119.8
O14—C14—C15	123.49 (8)	C7—C6—C5	118.85 (8)
H14—O14—C14	107.1	C4—C10—C5	122.32 (8)
O3—C3—C2	121.80 (6)	C12—C13—C14	120.48 (6)
O3—C3—C4	117.32 (7)	C12—C11—C16	118.52 (6)
H3—O3—C3	106.8	H12—C12—C13	119.4
H1W—O1W—H2W	102.8	C13—C14—C15	118.92 (6)
C10—C9—C8	122.01 (6)	C14—C15—C16	120.94 (8)
C10—C5—C6	120.75 (8)	C14—C15—H15	117.9
C10—C4—C3	117.32 (6)	C16—C15—H15	121.2
C2—O1—C9	122.00 (7)	H16—C16—C15	120.3
O13—C13—C14—O14	−2.48 (5)	C10—C9—O1—C2	−1.03 (6)
O13—C13—C14—C15	177.96 (6)	C10—C9—C8—C7	−1.03 (6)
O13—C13—C12—C11	−179.80 (6)	C10—C9—C8—H8	177.8
O13—C13—C12—H12	1.3	C10—C5—C6—C7	−0.53 (6)
H13—O13—C13—C14	177.9	C10—C5—C6—H6	−180.0
H13—O13—C13—C12	−1.6	C10—C4—C3—C2	0.02 (6)
O4—C4—C3—O3	1.67 (6)	C2—O1—C9—C8	178.79 (5)
O4—C4—C3—C2	179.89 (7)	C2—C11—C16—C15	179.55 (7)
O4—C4—C10—C9	179.34 (7)	C2—C11—C16—H16	0.0
O4—C4—C10—C5	−0.35 (6)	C2—C11—C12—C13	−179.51 (7)
O1—C9—C10—C5	−178.99 (6)	C2—C11—C12—H12	−0.6
O1—C9—C10—C4	1.31 (6)	C8—C9—C10—C5	1.20 (6)
O1—C9—C8—C7	179.16 (6)	C8—C9—C10—C4	−178.50 (6)
O1—C9—C8—H8	−2.0	C8—C7—C6—C5	0.72 (6)
O1—C2—C3—O3	178.42 (5)	C8—C7—C6—H6	−179.9
O1—C2—C3—C4	0.28 (6)	H8—C8—C7—C6	−178.8
O1—C2—C11—C16	−1.12 (6)	C9—O1—C2—C3	0.22 (6)
O1—C2—C11—C12	179.38 (5)	C9—O1—C2—C11	179.68 (5)
O7—C7—C8—C9	179.65 (7)	C9—C10—C5—C6	−0.40 (6)
O7—C7—C8—H8	0.8	C9—C10—C4—C3	−0.80 (6)
O7—C7—C6—C5	−178.87 (6)	C9—C8—C7—C6	0.05 (6)
O7—C7—C6—H6	0.6	C6—C5—C10—C4	179.30 (7)
H7—O7—C7—C8	−178.4	C11—C2—C3—C4	−179.09 (5)
H7—O7—C7—C6	1.2	C11—C16—C15—C14	−0.90 (6)
O5—C5—C10—C9	178.65 (6)	C11—C16—C15—H15	178.0
O5—C5—C10—C4	−1.66 (6)	C11—C12—C13—C14	0.79 (6)
O5—C5—C6—C7	−179.58 (7)	C3—C2—C11—C16	178.29 (6)
O5—C5—C6—H6	1.0	C3—C2—C11—C12	−1.21 (6)
H5—O5—C5—C10	2.1	C3—C4—C10—C5	179.51 (5)
H5—O5—C5—C6	−178.8	C12—C13—C14—C15	−2.60 (6)
O14—C14—C13—C12	176.96 (6)	C12—C11—C16—C15	−0.94 (6)
O14—C14—C15—C16	−176.87 (6)	C12—C11—C16—H16	179.5
O14—C14—C15—H15	4.2	H12—C12—C13—C14	−178.1
H14—O14—C14—C13	−173.0	H12—C12—C11—C16	179.9
H14—O14—C14—C15	6.5	C13—C14—C15—C16	2.66 (6)
O3—C3—C2—C11	−0.95 (6)	C13—C14—C15—H15	−176.3
O3—C3—C4—C10	−178.20 (7)	C13—C12—C11—C16	0.99 (6)
H3—O3—C3—C2	167.4	C14—C15—C16—H16	178.7
H3—O3—C3—C4	−14.4	H16—C16—C15—H15	−2.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O13^i	0.97	1.82	2.7815 (7)	177
O7—H7···O14^i	0.97	2.41	2.8449 (7)	107
O5—H5···O4	0.97	1.71	2.6066 (7)	152
O3—H3···O4	0.97	2.17	2.6937 (7)	113
C12—H12···O3	1.08	2.06	2.8139 (8)	124
O13—H13···O1W^ii	0.97	1.76	2.7113 (7)	169
O1W—H1W···O5^iii	0.97	2.21	3.0470 (8)	145
O1W—H1W···O5^iv	0.97	2.35	3.0455 (7)	128
O3—H3···O4^v	0.97	1.90	2.7046 (7)	139
O1W—H2W···O4^v	0.97	1.95	2.9059 (7)	172
O14—H14···O7^vi	0.97	1.84	2.8020 (7)	176

Symmetry codes: (i) x−1, y−2, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z; (vi) −x+1, y+3/2, −z+1/2.

2(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one monohydrate (TAAM_THEO_R)

Crystal data

C15H10O7·H2O	F(000) = 664
Mr = 320.24	Dx = 1.672 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 15541 reflections
a = 8.737 (1) Å	θ = 5.1–76.3°
b = 4.852 (1) Å	µ = 0.14 mm^−1
c = 30.160 (1) Å	T = 110 K
β = 95.52 (1)°	, yellow
V = 1272.6 (3) Å^3	0.35 × 0.19 × 0.16 mm
Z = 4

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	2652 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2565 reflections with > 2.0σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 10.4508 pixels mm^-1	θmax = 76.3°, θmin = 5.1°
ω scans	h = −11→10
Absorption correction: multi-scan 'Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'	k = 0→6
Tmin = 0.672, Tmax = 1.000	l = 0→37
69706 measured reflections

Refinement

Refinement on F	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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.027	H-atom parameters constrained
S = 1.11	w = 1/[3.68*σ^2(Fo^2) + 0.001*Yo^2]
2652 reflections	(Δ/^σ)max < 0.001
256 parameters	Δ^ρmax = 0.15 e Å−3
29 restraints	Δ^ρmin =^−0.18 e Å−3

Special details

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27–08-2009 CrysAlis171. NET) (compiled Aug 27 2009,17:19:36)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O13	0.88586 (5)	1.3933 (1)	0.13768 (2)	0.0148 (1)
H13	0.86933	1.36970	0.10573	0.02211*
O4	0.35006 (6)	0.4013 (1)	0.02131 (2)	0.0164 (1)
O1	0.42741 (5)	0.4791 (1)	0.15567 (1)	0.0121 (1)
O7	0.08417 (5)	−0.2283 (1)	0.18239 (2)	0.0145 (1)
H7	0.01406	−0.36324	0.16830	0.02173*
O5	0.14888 (6)	0.0177 (1)	0.03272 (2)	0.0185 (1)
H5	0.21333	0.14528	0.01833	0.02769*
O14	0.91022 (5)	1.3760 (1)	0.22606 (2)	0.0160 (1)
H14	0.91426	1.33526	0.25753	0.02392*
O3	0.55004 (6)	0.7850 (1)	0.05550 (2)	0.0187 (1)
H3	0.53414	0.70465	0.02607	0.02809*
O1W	0.86820 (6)	0.3661 (1)	0.04745 (2)	0.0245 (2)
H1W	0.93023	0.24425	0.03117	0.03666*
H2W	0.78805	0.42917	0.02543	0.03662*
C10	0.29380 (7)	0.2530 (1)	0.09281 (2)	0.0121 (2)
C2	0.50454 (7)	0.6458 (1)	0.12890 (2)	0.0120 (2)
C8	0.25569 (7)	0.1236 (1)	0.16915 (2)	0.0129 (2)
H8	0.28349	0.14528	0.20474	0.01556*
C9	0.32565 (7)	0.2858 (1)	0.13894 (2)	0.0114 (2)
C6	0.11213 (7)	−0.1107 (1)	0.10638 (2)	0.0135 (2)
H6	0.02920	−0.26522	0.09412	0.01632*
C11	0.60745 (7)	0.8393 (1)	0.15424 (2)	0.0122 (2)
C7	0.14942 (7)	−0.0732 (1)	0.15241 (2)	0.0124 (2)
C3	0.47916 (8)	0.6204 (1)	0.08335 (2)	0.0135 (2)
C4	0.37212 (7)	0.4214 (1)	0.06338 (2)	0.0131 (2)
C12	0.69859 (7)	1.0274 (1)	0.13283 (2)	0.0128 (2)
H12	0.69471	1.02758	0.09684	0.01542*
C13	0.79646 (7)	1.2082 (1)	0.15736 (2)	0.0125 (2)
C14	0.80773 (7)	1.2040 (1)	0.20400 (2)	0.0131 (2)
C5	0.18444 (7)	0.0505 (1)	0.07700 (2)	0.0135 (2)
C16	0.61617 (8)	0.8416 (2)	0.20098 (2)	0.0146 (2)
H16	0.54564	0.69995	0.21787	0.01757*
C15	0.71456 (8)	1.0237 (2)	0.22532 (2)	0.0150 (2)
H15	0.72007	1.03153	0.26133	0.01795*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0163 (2)	0.0153 (3)	0.0126 (2)	−0.0052 (2)	0.0018 (2)	−0.0007 (2)
O4	0.0187 (3)	0.0199 (3)	0.0106 (2)	−0.0062 (2)	0.0020 (2)	−0.0006 (2)
O1	0.0136 (2)	0.0126 (3)	0.0099 (2)	−0.0027 (2)	0.0005 (2)	−0.0003 (2)
O7	0.0165 (2)	0.0146 (3)	0.0122 (2)	−0.0045 (2)	0.0017 (2)	0.0006 (2)
O5	0.0218 (3)	0.0219 (3)	0.0116 (2)	−0.0093 (2)	0.0004 (2)	−0.0023 (2)
O14	0.0179 (2)	0.0168 (3)	0.0131 (2)	−0.0063 (2)	0.00016 (18)	0.00012 (19)
O3	0.0233 (3)	0.0208 (3)	0.0121 (2)	−0.0106 (2)	0.0041 (2)	−0.0014 (2)
O1W	0.0280 (3)	0.0311 (3)	0.0139 (2)	0.0029 (2)	−0.0013 (2)	−0.0014 (2)
C10	0.0127 (3)	0.0127 (3)	0.0107 (3)	−0.0021 (2)	0.0008 (2)	−0.0005 (2)
C2	0.0121 (3)	0.0118 (3)	0.0119 (3)	−0.0019 (2)	0.0012 (2)	−0.0009 (2)
C8	0.0146 (3)	0.0135 (3)	0.0106 (3)	−0.0023 (2)	0.0014 (2)	0.0000 (2)
C9	0.0122 (3)	0.0112 (3)	0.0108 (3)	−0.0012 (2)	0.0012 (2)	−0.0003 (2)
C6	0.0138 (3)	0.0136 (3)	0.0131 (3)	−0.0036 (2)	0.0014 (2)	−0.0013 (2)
C11	0.0122 (3)	0.0125 (3)	0.0118 (3)	−0.0022 (2)	0.0009 (2)	−0.0002 (2)
C7	0.0124 (3)	0.0124 (3)	0.0123 (3)	−0.0012 (2)	0.0016 (2)	0.0004 (2)
C3	0.0146 (3)	0.0143 (4)	0.0116 (3)	−0.0037 (2)	0.0024 (2)	−0.0010 (2)
C4	0.0141 (3)	0.0146 (4)	0.0107 (3)	−0.0028 (2)	0.0015 (2)	−0.0006 (2)
C12	0.0132 (3)	0.0133 (3)	0.0119 (3)	−0.0028 (2)	0.0010 (2)	0.0002 (2)
C13	0.0126 (3)	0.0122 (3)	0.0127 (3)	−0.0024 (2)	0.0010 (2)	0.0001 (2)
C14	0.0138 (3)	0.0130 (3)	0.0125 (3)	−0.0022 (2)	0.0003 (2)	0.0003 (2)
C5	0.0143 (3)	0.0145 (4)	0.0116 (3)	−0.0031 (2)	0.0013 (2)	−0.0009 (2)
C16	0.0163 (3)	0.0151 (4)	0.0123 (3)	−0.0045 (2)	0.0010 (2)	0.0004 (3)
C15	0.0173 (3)	0.0162 (4)	0.0114 (3)	−0.0050 (3)	0.0008 (2)	0.0001 (3)

Geometric parameters (Å, º)

O13—C13	1.3633 (8)	C2—C3	1.3760 (9)
O13—H13	0.967	C2—C11	1.4633 (9)
O4—C4	1.2688 (8)	C8—C9	1.3894 (9)
O1—C9	1.3560 (8)	C8—C7	1.3923 (9)
O1—C2	1.3654 (8)	C8—H8	1.083
O7—C7	1.3448 (8)	C6—C5	1.3800 (9)
O7—H7	0.967	C6—C7	1.4070 (9)
O5—C5	1.3512 (8)	C6—H6	1.083
O5—H5	0.967	C11—C16	1.4045 (9)
O14—C14	1.3511 (8)	C11—C12	1.4083 (9)
O14—H14	0.967	C3—C4	1.4357 (9)
O3—C3	1.3515 (8)	C12—C13	1.3877 (9)
O3—H3	0.967	C12—H12	1.083
O1W—H2W	0.967	C13—C14	1.4009 (9)
O1W—H1W	0.967	C14—C15	1.3937 (9)
C10—C9	1.4014 (9)	C16—C15	1.3916 (9)
C10—C5	1.4204 (9)	C16—H16	1.083
C10—C4	1.4284 (9)	C15—H15	1.083
O13—C13—C14	117.31 (6)	C2—C3—C4	120.99 (7)
O13—C13—C12	122.26 (8)	C2—C11—C16	120.05 (6)
H13—O13—C13	108.6	C2—C11—C12	121.50 (6)
O4—C4—C3	120.10 (6)	C8—C7—C6	121.97 (8)
O4—C4—C10	122.78 (6)	H8—C8—C9	121.6
O1—C9—C10	120.57 (7)	H8—C8—C7	120.3
O1—C9—C8	117.50 (7)	C9—C10—C5	118.34 (7)
O1—C2—C3	119.73 (8)	C9—C10—C4	119.37 (7)
O1—C2—C11	112.62 (5)	C9—C8—C7	118.09 (8)
O7—C7—C8	116.82 (6)	H6—C6—C5	120.4
O7—C7—C6	121.21 (8)	H6—C6—C7	120.7
H7—O7—C7	112.0	C11—C2—C3	127.65 (8)
O5—C5—C10	119.77 (6)	C11—C16—C15	120.38 (7)
O5—C5—C6	119.47 (6)	C11—C16—H16	119.3
H5—O5—C5	106.2	C11—C12—C13	120.79 (6)
O14—C14—C13	117.70 (7)	C11—C12—H12	119.7
O14—C14—C15	123.33 (8)	C7—C6—C5	118.90 (8)
H14—O14—C14	108.5	C4—C10—C5	122.29 (8)
O3—C3—C2	121.89 (6)	C12—C13—C14	120.43 (6)
O3—C3—C4	117.09 (7)	C12—C11—C16	118.45 (6)
H3—O3—C3	107.4	H12—C12—C13	119.5
H1W—O1W—H2W	104.4	C13—C14—C15	118.97 (6)
C10—C9—C8	121.93 (6)	C14—C15—C16	120.92 (8)
C10—C5—C6	120.75 (8)	C14—C15—H15	118.0
C10—C4—C3	117.12 (6)	C16—C15—H15	121.1
C2—O1—C9	122.20 (7)	H16—C16—C15	120.4
O13—C13—C14—O14	−2.43 (5)	C10—C9—O1—C2	−1.06 (6)
O13—C13—C14—C15	177.98 (6)	C10—C9—C8—C7	−1.00 (6)
O13—C13—C12—C11	−179.81 (6)	C10—C9—C8—H8	178.0
O13—C13—C12—H12	1.9	C10—C5—C6—C7	−0.54 (6)
H13—O13—C13—C14	178.1	C10—C5—C6—H6	−179.8
H13—O13—C13—C12	−1.3	C10—C4—C3—C2	0.10 (6)
O4—C4—C3—O3	1.59 (6)	C2—O1—C9—C8	178.79 (5)
O4—C4—C3—C2	179.90 (7)	C2—C11—C16—C15	179.55 (7)
O4—C4—C10—C9	179.35 (7)	C2—C11—C16—H16	−0.3
O4—C4—C10—C5	−0.30 (6)	C2—C11—C12—C13	−179.52 (7)
O1—C9—C10—C5	−178.99 (6)	C2—C11—C12—H12	−1.2
O1—C9—C10—C4	1.35 (6)	C8—C9—C10—C5	1.17 (6)
O1—C9—C8—C7	179.15 (6)	C8—C9—C10—C4	−178.50 (6)
O1—C9—C8—H8	−1.9	C8—C7—C6—C5	0.72 (6)
O1—C2—C3—O3	178.43 (5)	C8—C7—C6—H6	179.9
O1—C2—C3—C4	0.21 (5)	H8—C8—C7—C6	−178.9
O1—C2—C11—C16	−1.10 (6)	C9—O1—C2—C3	0.27 (6)
O1—C2—C11—C12	179.39 (5)	C9—O1—C2—C11	179.69 (5)
O7—C7—C8—C9	179.62 (7)	C9—C10—C5—C6	−0.37 (6)
O7—C7—C8—H8	0.6	C9—C10—C4—C3	−0.86 (6)
O7—C7—C6—C5	−178.84 (6)	C9—C8—C7—C6	0.03 (6)
O7—C7—C6—H6	0.4	C6—C5—C10—C4	179.28 (7)
H7—O7—C7—C8	−178.4	C11—C2—C3—C4	−179.12 (5)
H7—O7—C7—C6	1.2	C11—C16—C15—C14	−0.91 (6)
O5—C5—C10—C9	178.66 (6)	C11—C16—C15—H15	178.3
O5—C5—C10—C4	−1.69 (6)	C11—C12—C13—C14	0.82 (6)
O5—C5—C6—C7	−179.57 (7)	C3—C2—C11—C16	178.28 (6)
O5—C5—C6—H6	1.2	C3—C2—C11—C12	−1.24 (6)
H5—O5—C5—C10	2.4	C3—C4—C10—C5	179.49 (5)
H5—O5—C5—C6	−178.6	C12—C13—C14—C15	−2.62 (6)
O14—C14—C13—C12	176.97 (6)	C12—C11—C16—C15	−0.91 (6)
O14—C14—C15—C16	−176.90 (6)	C12—C11—C16—H16	179.2
O14—C14—C15—H15	3.9	H12—C12—C13—C14	−177.5
H14—O14—C14—C13	−173.2	H12—C12—C11—C16	179.3
H14—O14—C14—C15	6.4	C13—C14—C15—C16	2.67 (6)
O3—C3—C2—C11	−0.90 (6)	C13—C14—C15—H15	−176.6
O3—C3—C4—C10	−178.20 (7)	C13—C12—C11—C16	0.96 (6)
H3—O3—C3—C2	167.1	C14—C15—C16—H16	179.0
H3—O3—C3—C4	−14.6	H16—C16—C15—H15	−1.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O13^i	0.97	1.82	2.7824 (7)	176
O7—H7···O14^i	0.97	2.40	2.8487 (7)	108
O5—H5···O4	0.97	1.72	2.6052 (7)	151
O3—H3···O4	0.97	2.17	2.6897 (7)	112
C12—H12···O3	1.08	2.06	2.8154 (8)	124
O13—H13···O1W^ii	0.97	1.76	2.7140 (7)	170
O1W—H1W···O5^iii	0.97	2.20	3.0460 (8)	145
O1W—H1W···O5^iv	0.97	2.36	3.0442 (7)	128
O3—H3···O4^v	0.97	1.90	2.7081 (7)	139
O1W—H2W···O4^v	0.97	1.95	2.9069 (7)	171
O14—H14···O7^vi	0.97	1.84	2.8028 (7)	177

Symmetry codes: (i) x−1, y−2, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z; (vi) −x+1, y+3/2, −z+1/2.