(+)-Pinoresinol–dioxane (1/1)

Stomberg, R.; Ibrahim, W.; Langer, V.; Lundquist, K.

doi:10.1107/S1600536803026114

(+)-Pinoresinol-dioxane (1/1)

R. Stomberg, W. Ibrahim, V. Langer and K. Lundquist

The crystal structure of a dioxane solvate of (+)-pinoresinol, C₂₀H₂₂O₆·C₄H₈O₂, has been determined. The solvate is stabilized by hydrogen bonding between the pinoresinol and dioxane molecules. The five-membered rings in the central dioxabicyclooctane ring system of the pinoresinol molecules adopt envelope conformations, with the benzylic C atoms as flaps.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026114/na6268sup1.cif Contains datablocks I, n
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026114/na6268Isup2.hkl Contains datablock I

CCDC reference: 227900

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.121
Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?
PLAT481_ALERT_4_A Long D...A H-Bond Reported [C]O6  ..  O5       =       2.66 Ang.

Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         93 PerFit
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          c
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup .      P21/c

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.61
PLAT481_ALERT_4_C Long D...A H-Bond Reported [F]C23 ..  O3       =       3.46 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported [G]C23 ..  O4       =       3.48 Ang.
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........      [A]O2
                    [A]O2  H2A
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........      [B]O2
                    [B]O2  H2A
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........      [C]O6
                    [C]O6  H6A
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........      [D]O6
                    [D]O6  H6A
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........     [E]C19
                    [E]C19 H19
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........     [F]C23
                    [F]C23 H23A
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........     [G]C23
                    [G]C23 H23B
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........      [A]O2
                    [A]O2  O1
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........      [B]O2
                    [B]O2  O8
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........      [C]O6
                    [C]O6  O5
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........      [D]O6
                    [D]O6  O7
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........     [E]C19
                    [E]C19 O6
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........     [F]C23
                    [F]C23 O3
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........     [G]C23
                    [G]C23 O4
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........      [A]O2
                    [A]O2  H2A    O1
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........      [B]O2
                    [B]O2  H2A    O8
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........      [C]O6
                    [C]O6  H6A    O5
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........      [D]O6
                    [D]O6  H6A    O7
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........     [E]C19
                    [E]C19 H19    O6
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........     [F]C23
                    [F]C23 H23A   O3
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........     [G]C23
                    [G]C23 H23B   O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C4 H8 O2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.97
           From the CIF: _reflns_number_total               3479
           Count of symmetry unique reflns         3483
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   2 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  26 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

  23 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: TEXSAN-TEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXSAN-TEXRAY; data reduction: TEXSAN-TEXRAY; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.

(+)-pinoresinol–dioxane (1/1) top

Crystal data top

C₂₀H₂₂O₆·C₄H₈O₂	F(000) = 476
M_r = 446.48	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.8318 (16) Å	θ = 23.4–24.9°
b = 6.066 (3) Å	µ = 0.10 mm⁻¹
c = 18.493 (2) Å	T = 153 K
β = 92.891 (13)°	Plate, colourless
V = 1101.5 (6) Å³	0.55 × 0.35 × 0.35 mm
Z = 2

Data collection top

Rigaku AFC6 diffractometer	R_int = 0.013
Radiation source: normal-focus rotating anode	θ_max = 30.0°, θ_min = 2.1°
Graphite monochromator	h = 0→13
ω scans	k = 0→8
3660 measured reflections	l = −25→25
3479 independent reflections	3 standard reflections every 150 reflections
2765 reflections with I > 2σ_I	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0679P)² + 0.1302P] where P = (F_o² + 2F_c²)/3
3479 reflections	(Δ/σ)_max < 0.001
311 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Special details top

Experimental. Data were collected at low temperature using a Rigaku AFC6R diffractometer equiped with a low temperature device. The data were collected using ω-scan. Scans of (1.22 + 0.30tanθ) were made at a speed of 8.0ο/min. The weak reflections (I<10.0σ_I) were rescanned (maximum 3 rescans) and the counts were accumulated to assure good counting statistics. Stationary bacground counts were recored on each side of the reflection. The ratio of peak counting time to backgroud counting time was 2:1. The crystal–to–detector distance was 400 mm.

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

	x	y	z	U_iso*/U_eq
C1	0.86723 (18)	0.7651 (4)	0.39457 (10)	0.0237 (4)
C2	0.78063 (19)	0.6263 (4)	0.43133 (10)	0.0248 (4)
H2	0.7484	0.4974	0.4093	0.042 (8)*
C3	0.74239 (18)	0.6788 (4)	0.50015 (10)	0.0228 (4)
C4	0.79078 (19)	0.8737 (4)	0.53375 (10)	0.0245 (4)
C5	0.8747 (2)	1.0127 (4)	0.49705 (11)	0.0273 (4)
H5	0.9060	1.1427	0.5188	0.043 (8)*
C6	0.91258 (19)	0.9590 (4)	0.42766 (11)	0.0262 (4)
H6	0.9688	1.0539	0.4033	0.042 (8)*
C7	0.5873 (2)	0.3774 (4)	0.50649 (13)	0.0316 (5)
H7A	0.5392	0.4286	0.4632	0.036 (7)*
H7B	0.5237	0.3164	0.5387	0.052 (9)*
H7C	0.6516	0.2661	0.4942	0.044 (8)*
C8	0.91926 (19)	0.6906 (4)	0.32359 (10)	0.0255 (4)
H8	0.9848	0.5711	0.3331	0.038 (7)*
C9	0.9850 (2)	0.8631 (4)	0.27647 (10)	0.0263 (4)
H9	0.9351	1.0029	0.2765	0.029 (7)*
C10	1.1386 (2)	0.8986 (5)	0.29093 (11)	0.0335 (5)
H10A	1.1580	1.0537	0.2991	0.040*
H10B	1.1708	0.8164	0.3334	0.040*
C11	1.15336 (18)	0.6312 (4)	0.11523 (10)	0.0254 (4)
C12	1.23149 (19)	0.7870 (4)	0.08078 (10)	0.0261 (4)
H12	1.2661	0.9084	0.1063	0.046 (8)*
C13	1.25762 (19)	0.7606 (4)	0.00794 (10)	0.0250 (4)
C14	1.20537 (19)	0.5794 (4)	−0.03067 (10)	0.0276 (4)
C15	1.1261 (2)	0.4272 (4)	0.00362 (11)	0.0311 (5)
H15	1.0891	0.3081	−0.0222	0.039 (8)*
C16	1.1013 (2)	0.4517 (4)	0.07677 (11)	0.0293 (4)
H16	1.0495	0.3471	0.0998	0.034 (7)*
C17	1.4086 (2)	1.0689 (4)	0.00630 (13)	0.0339 (5)
H17A	1.3457	1.1710	0.0260	0.045 (8)*
H17B	1.4651	1.1451	−0.0264	0.051 (9)*
H17C	1.4646	1.0053	0.0449	0.048 (8)*
C18	1.11777 (19)	0.6620 (4)	0.19303 (10)	0.0262 (4)
H18	1.1279	0.5212	0.2187	0.039 (7)*
C19	0.97340 (19)	0.7513 (4)	0.20150 (10)	0.0283 (4)
H19	0.9491	0.8590	0.1635	0.033 (7)*
C20	0.8610 (2)	0.5794 (6)	0.20753 (11)	0.0430 (7)
H20A	0.7896	0.6026	0.1702	0.052*
H20B	0.8975	0.4321	0.2022	0.052*
C21	1.4511 (3)	0.5275 (5)	−0.23373 (13)	0.0390 (6)
H21A	1.3798	0.4182	−0.2299	0.047*
H21B	1.5376	0.4575	−0.2206	0.047*
C22	1.4521 (3)	0.6092 (6)	−0.30944 (13)	0.0560 (9)
H22A	1.4701	0.4875	−0.3416	0.067*
H22B	1.3633	0.6694	−0.3237	0.067*
C23	1.5316 (2)	0.9530 (5)	−0.26788 (13)	0.0366 (5)
H23A	1.4453	1.0235	−0.2811	0.044*
H23B	1.6033	1.0617	−0.2715	0.044*
C24	1.5301 (3)	0.8708 (6)	−0.19247 (13)	0.0517 (8)
H24A	1.6188	0.8103	−0.1782	0.062*
H24B	1.5124	0.9927	−0.1603	0.062*
O1	0.65778 (15)	0.5576 (3)	0.54108 (7)	0.0295 (3)
O2	0.75570 (17)	0.9280 (3)	0.60194 (8)	0.0353 (4)
H2A	0.6918	0.8507	0.6134	0.051 (9)*
O3	0.80826 (15)	0.6066 (4)	0.27825 (8)	0.0402 (5)
O4	1.20418 (14)	0.8221 (4)	0.22813 (7)	0.0348 (4)
O5	1.33514 (16)	0.8991 (3)	−0.03163 (8)	0.0326 (4)
O6	1.23224 (18)	0.5481 (4)	−0.10141 (8)	0.0416 (5)
H6A	1.2894	0.6379	−0.1133	0.060 (10)*
O7	1.42862 (19)	0.7052 (4)	−0.18529 (9)	0.0434 (5)
O8	1.5538 (2)	0.7757 (4)	−0.31618 (9)	0.0467 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0198 (7)	0.0274 (10)	0.0239 (8)	−0.0003 (8)	0.0016 (6)	−0.0013 (8)
C2	0.0229 (8)	0.0262 (10)	0.0253 (8)	−0.0019 (8)	0.0010 (7)	−0.0011 (8)
C3	0.0199 (8)	0.0233 (9)	0.0253 (8)	−0.0033 (8)	0.0019 (6)	0.0011 (8)
C4	0.0225 (8)	0.0279 (10)	0.0230 (8)	−0.0008 (8)	0.0005 (7)	−0.0014 (8)
C5	0.0260 (9)	0.0268 (10)	0.0291 (9)	−0.0053 (9)	0.0022 (7)	−0.0030 (9)
C6	0.0218 (8)	0.0301 (11)	0.0269 (9)	−0.0045 (8)	0.0034 (7)	0.0024 (8)
C7	0.0295 (10)	0.0225 (10)	0.0435 (12)	−0.0056 (9)	0.0079 (9)	−0.0025 (9)
C8	0.0216 (8)	0.0303 (10)	0.0247 (8)	−0.0028 (8)	0.0025 (6)	−0.0043 (8)
C9	0.0258 (9)	0.0314 (11)	0.0217 (8)	−0.0006 (8)	0.0024 (7)	0.0001 (8)
C10	0.0300 (10)	0.0448 (14)	0.0260 (9)	−0.0095 (10)	0.0048 (7)	−0.0041 (10)
C11	0.0194 (8)	0.0326 (11)	0.0244 (8)	0.0010 (8)	0.0022 (6)	0.0006 (8)
C12	0.0231 (8)	0.0283 (10)	0.0270 (8)	−0.0015 (8)	0.0017 (7)	−0.0029 (9)
C13	0.0205 (8)	0.0285 (10)	0.0262 (8)	−0.0014 (8)	0.0024 (6)	0.0012 (8)
C14	0.0232 (8)	0.0359 (12)	0.0241 (8)	−0.0034 (9)	0.0035 (7)	−0.0021 (9)
C15	0.0275 (9)	0.0345 (12)	0.0315 (10)	−0.0094 (10)	0.0029 (8)	−0.0066 (10)
C16	0.0256 (9)	0.0322 (11)	0.0305 (10)	−0.0063 (9)	0.0058 (7)	0.0001 (9)
C17	0.0349 (10)	0.0250 (11)	0.0424 (11)	−0.0069 (9)	0.0085 (9)	−0.0043 (10)
C18	0.0225 (8)	0.0315 (11)	0.0247 (8)	0.0001 (8)	0.0015 (7)	0.0002 (8)
C19	0.0216 (8)	0.0416 (13)	0.0215 (8)	0.0014 (9)	−0.0006 (6)	−0.0002 (9)
C20	0.0276 (10)	0.072 (2)	0.0301 (10)	−0.0145 (13)	0.0072 (8)	−0.0175 (13)
C21	0.0431 (12)	0.0302 (12)	0.0450 (13)	−0.0026 (11)	0.0132 (10)	−0.0003 (11)
C22	0.086 (2)	0.0508 (18)	0.0323 (12)	−0.0345 (18)	0.0166 (13)	−0.0117 (13)
C23	0.0334 (11)	0.0323 (12)	0.0451 (12)	−0.0046 (10)	0.0103 (9)	−0.0004 (11)
C24	0.0679 (18)	0.0539 (19)	0.0340 (12)	−0.0288 (16)	0.0099 (12)	−0.0092 (13)
O1	0.0336 (7)	0.0288 (8)	0.0265 (7)	−0.0088 (7)	0.0062 (5)	0.0006 (7)
O2	0.0397 (8)	0.0402 (10)	0.0267 (7)	−0.0131 (8)	0.0092 (6)	−0.0074 (7)
O3	0.0266 (7)	0.0652 (13)	0.0294 (7)	−0.0172 (9)	0.0071 (6)	−0.0143 (9)
O4	0.0235 (6)	0.0541 (11)	0.0270 (7)	−0.0086 (8)	0.0037 (5)	−0.0078 (8)
O5	0.0337 (7)	0.0341 (9)	0.0304 (7)	−0.0121 (8)	0.0053 (6)	−0.0010 (7)
O6	0.0446 (9)	0.0542 (12)	0.0272 (7)	−0.0235 (10)	0.0113 (7)	−0.0108 (8)
O7	0.0540 (10)	0.0442 (11)	0.0339 (8)	−0.0168 (9)	0.0202 (7)	−0.0077 (9)
O8	0.0623 (11)	0.0427 (11)	0.0375 (8)	−0.0181 (11)	0.0263 (8)	−0.0075 (9)

Geometric parameters (Å, º) top

C1—C6	1.390 (3)	C14—C15	1.383 (3)
C1—C2	1.398 (3)	C15—C16	1.395 (3)
C1—C8	1.502 (3)	C15—H15	0.9300
C2—C3	1.382 (3)	C16—H16	0.9300
C2—H2	0.9300	C17—O5	1.423 (3)
C3—O1	1.367 (2)	C17—H17A	0.9600
C3—C4	1.407 (3)	C17—H17B	0.9600
C4—O2	1.364 (2)	C17—H17C	0.9600
C4—C5	1.382 (3)	C18—O4	1.425 (3)
C5—C6	1.393 (3)	C18—C19	1.535 (3)
C5—H5	0.9300	C18—H18	0.9800
C6—H6	0.9300	C19—C20	1.528 (4)
C7—O1	1.428 (3)	C19—H19	0.9800
C7—H7A	0.9600	C20—O3	1.441 (2)
C7—H7B	0.9600	C20—H20A	0.9700
C7—H7C	0.9600	C20—H20B	0.9700
C8—O3	1.436 (2)	C21—O7	1.426 (3)
C8—C9	1.526 (3)	C21—C22	1.486 (4)
C8—H8	0.9800	C21—H21A	0.9700
C9—C10	1.535 (3)	C21—H21B	0.9700
C9—C19	1.542 (3)	C22—O8	1.431 (3)
C9—H9	0.9800	C22—H22A	0.9700
C10—O4	1.434 (2)	C22—H22B	0.9700
C10—H10A	0.9700	C23—O8	1.422 (3)
C10—H10B	0.9700	C23—C24	1.482 (4)
C11—C16	1.384 (3)	C23—H23A	0.9700
C11—C12	1.392 (3)	C23—H23B	0.9700
C11—C18	1.509 (3)	C24—O7	1.427 (3)
C12—C13	1.393 (3)	C24—H24A	0.9700
C12—H12	0.9300	C24—H24B	0.9700
C13—O5	1.370 (3)	O2—H2A	0.8200
C13—C14	1.395 (3)	O6—H6A	0.8200
C14—O6	1.361 (2)

C6—C1—C2	119.04 (18)	C11—C16—H16	119.9
C6—C1—C8	121.58 (18)	C15—C16—H16	119.9
C2—C1—C8	119.12 (19)	O5—C17—H17A	109.5
C3—C2—C1	120.7 (2)	O5—C17—H17B	109.5
C3—C2—H2	119.7	H17A—C17—H17B	109.5
C1—C2—H2	119.7	O5—C17—H17C	109.5
O1—C3—C2	126.0 (2)	H17A—C17—H17C	109.5
O1—C3—C4	114.12 (17)	H17B—C17—H17C	109.5
C2—C3—C4	119.89 (19)	O4—C18—C11	110.93 (17)
O2—C4—C5	119.4 (2)	O4—C18—C19	104.25 (18)
O2—C4—C3	121.02 (19)	C11—C18—C19	113.65 (16)
C5—C4—C3	119.53 (18)	O4—C18—H18	109.3
C4—C5—C6	120.3 (2)	C11—C18—H18	109.3
C4—C5—H5	119.9	C19—C18—H18	109.3
C6—C5—H5	119.9	C20—C19—C18	116.3 (2)
C1—C6—C5	120.60 (19)	C20—C19—C9	104.80 (16)
C1—C6—H6	119.7	C18—C19—C9	102.70 (15)
C5—C6—H6	119.7	C20—C19—H19	110.8
O1—C7—H7A	109.5	C18—C19—H19	110.8
O1—C7—H7B	109.5	C9—C19—H19	110.8
H7A—C7—H7B	109.5	O3—C20—C19	106.4 (2)
O1—C7—H7C	109.5	O3—C20—H20A	110.4
H7A—C7—H7C	109.5	C19—C20—H20A	110.4
H7B—C7—H7C	109.5	O3—C20—H20B	110.4
O3—C8—C1	109.55 (15)	C19—C20—H20B	110.4
O3—C8—C9	103.96 (16)	H20A—C20—H20B	108.6
C1—C8—C9	117.75 (19)	O7—C21—C22	110.4 (2)
O3—C8—H8	108.4	O7—C21—H21A	109.6
C1—C8—H8	108.4	C22—C21—H21A	109.6
C9—C8—H8	108.4	O7—C21—H21B	109.6
C8—C9—C10	115.99 (18)	C22—C21—H21B	109.6
C8—C9—C19	101.40 (18)	H21A—C21—H21B	108.1
C10—C9—C19	104.24 (16)	O8—C22—C21	110.8 (2)
C8—C9—H9	111.5	O8—C22—H22A	109.5
C10—C9—H9	111.5	C21—C22—H22A	109.5
C19—C9—H9	111.5	O8—C22—H22B	109.5
O4—C10—C9	106.99 (16)	C21—C22—H22B	109.5
O4—C10—H10A	110.3	H22A—C22—H22B	108.1
C9—C10—H10A	110.3	O8—C23—C24	110.2 (3)
O4—C10—H10B	110.3	O8—C23—H23A	109.6
C9—C10—H10B	110.3	C24—C23—H23A	109.6
H10A—C10—H10B	108.6	O8—C23—H23B	109.6
C16—C11—C12	119.81 (18)	C24—C23—H23B	109.6
C16—C11—C18	119.32 (19)	H23A—C23—H23B	108.1
C12—C11—C18	120.8 (2)	O7—C24—C23	111.4 (2)
C11—C12—C13	119.8 (2)	O7—C24—H24A	109.4
C11—C12—H12	120.1	C23—C24—H24A	109.4
C13—C12—H12	120.1	O7—C24—H24B	109.4
O5—C13—C12	125.5 (2)	C23—C24—H24B	109.4
O5—C13—C14	114.22 (17)	H24A—C24—H24B	108.0
C12—C13—C14	120.29 (19)	C3—O1—C7	117.29 (16)
O6—C14—C15	119.3 (2)	C4—O2—H2A	109.5
O6—C14—C13	121.2 (2)	C8—O3—C20	105.85 (15)
C15—C14—C13	119.55 (18)	C18—O4—C10	107.89 (16)
C14—C15—C16	120.3 (2)	C13—O5—C17	117.57 (17)
C14—C15—H15	119.9	C14—O6—H6A	109.5
C16—C15—H15	119.9	C24—O7—C21	110.02 (19)
C11—C16—C15	120.3 (2)	C23—O8—C22	110.41 (18)

C6—C1—C2—C3	−1.2 (3)	C12—C11—C16—C15	−0.4 (3)
C8—C1—C2—C3	173.12 (18)	C18—C11—C16—C15	176.1 (2)
C1—C2—C3—O1	179.45 (19)	C14—C15—C16—C11	1.4 (3)
C1—C2—C3—C4	0.0 (3)	C16—C11—C18—O4	166.43 (19)
O1—C3—C4—O2	1.2 (3)	C12—C11—C18—O4	−17.1 (3)
C2—C3—C4—O2	−179.30 (19)	C16—C11—C18—C19	−76.5 (3)
O1—C3—C4—C5	−178.51 (19)	C12—C11—C18—C19	100.0 (2)
C2—C3—C4—C5	1.0 (3)	O4—C18—C19—C20	−148.36 (17)
O2—C4—C5—C6	179.4 (2)	C11—C18—C19—C20	90.7 (2)
C3—C4—C5—C6	−0.8 (3)	O4—C18—C19—C9	−34.6 (2)
C2—C1—C6—C5	1.3 (3)	C11—C18—C19—C9	−155.47 (19)
C8—C1—C6—C5	−172.8 (2)	C8—C9—C19—C20	20.3 (2)
C4—C5—C6—C1	−0.3 (3)	C10—C9—C19—C20	141.1 (2)
C6—C1—C8—O3	−138.4 (2)	C8—C9—C19—C18	−101.68 (19)
C2—C1—C8—O3	47.5 (3)	C10—C9—C19—C18	19.1 (2)
C6—C1—C8—C9	−19.9 (3)	C18—C19—C20—O3	116.6 (2)
C2—C1—C8—C9	165.94 (18)	C9—C19—C20—O3	4.0 (3)
O3—C8—C9—C10	−150.31 (19)	O7—C21—C22—O8	57.5 (3)
C1—C8—C9—C10	88.3 (2)	O8—C23—C24—O7	−57.5 (3)
O3—C8—C9—C19	−38.1 (2)	C2—C3—O1—C7	−9.3 (3)
C1—C8—C9—C19	−159.49 (16)	C4—C3—O1—C7	170.11 (17)
C8—C9—C10—O4	112.8 (2)	C1—C8—O3—C20	169.2 (2)
C19—C9—C10—O4	2.3 (3)	C9—C8—O3—C20	42.5 (3)
C16—C11—C12—C13	−0.5 (3)	C19—C20—O3—C8	−28.8 (3)
C18—C11—C12—C13	−176.90 (18)	C11—C18—O4—C10	160.50 (19)
C11—C12—C13—O5	−178.5 (2)	C19—C18—O4—C10	37.8 (2)
C11—C12—C13—C14	0.3 (3)	C9—C10—O4—C18	−25.2 (3)
O5—C13—C14—O6	0.4 (3)	C12—C13—O5—C17	8.0 (3)
C12—C13—C14—O6	−178.5 (2)	C14—C13—O5—C17	−170.81 (18)
O5—C13—C14—C15	179.7 (2)	C23—C24—O7—C21	57.4 (3)
C12—C13—C14—C15	0.7 (3)	C22—C21—O7—C24	−57.0 (3)
O6—C14—C15—C16	177.7 (2)	C24—C23—O8—C22	56.9 (3)
C13—C14—C15—C16	−1.6 (3)	C21—C22—O8—C23	−57.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
[a]O2—H2A···O1	0.82	2.24	2.671 (3)	113
[b]O2—H2A···O8ⁱ	0.82	1.98	2.718 (2)	149
[c]O6—H6A···O5	0.82	2.22	2.663 (3)	114
[d]O6—H6A···O7	0.82	2.00	2.710 (2)	145
[e]C19—H19···O6ⁱⁱ	0.98	2.37	3.221 (3)	145
[f]C23—H23A···O3ⁱⁱ	0.97	2.55	3.465 (3)	158
[g]C23—H23B···O4ⁱⁱⁱ	0.97	2.56	3.480 (3)	158

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

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